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【结 构 式】 
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【分子编号】16824 【品名】2-cyclopropylacetonitrile; Cyclopropylacetonitrile 【CA登记号】6542-60-5 |
【 分 子 式 】C5H7N 【 分 子 量 】81.11732 【元素组成】C 74.03% H 8.7% N 17.27% |
合成路线1
该中间体在本合成路线中的序号：(VI)The reaction of 3-chlorotetrafluoropyridine (I) with sodium tert-butoxide in THF gives 4-tert-butoxy-3-chloro-2,5,6-trifluoropyridine (II), which is dechlorinated with H2 over Pd/C in methanol yielding 4-tert-butoxy-2,3,6-trifluoropyridine (III). The methylation of (III) with methyl iodide and lithium diethylamide (LDA) in THF affords 4-tert-butoxy-2,3,6-trifluoro-5-methylpyridine (IV), which is selectively defluorinated with hydrazine in refluxing propanol to give 4-tert-butoxy-2,5-difluoro-3-methylpyridine (V). The condensation of (V) with cyclopropylacetonitrile (VI) by means of LDA in THF yields 2-(4-tert-butoxy-5-fluoro-3-methyl-2-pyridyl)-2-cyclopropylacetonitrile (VII), which is treated first with trifluoroacetic acid and then with POCl3 to afford 2-(4-chloro-5-fluoro-3-methyl-2-pyridyl)-2-cyclopropylacetonitrile (VIII). The alcoholysis of (VIII) with ethanol/HCl gives the corresponding ethyl ester (IX), which is partially reduced with LiAlH4 in THF to afford the corresponding aldehyde (X). The condensation of (X) with diethyl malonate (XI) by means of piperidine in refluxing ethanol yields the ethylidenemalonate (XII), which, without isolation, is cyclized by heating at 235 C in Dowtherm to afford 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester (XIII). The reaction of (XIII) with 3(S)-(tert-butoxycarbonylamino)pyrrolidine (XIV) by means of NaHCO3 in acetonitrile gives the corresponding condensation product (XV), which is hydrolyzed ith LiOH in THF/water to the corresponding free acid (XVI). Finally, this compound is deprotected with 4N HCl in dioxandichloromethane.
| 【1】 Fromtling, R.A.; Castañer, J.; ABT-719. Drugs Fut 1995, 20, 11, 1103. |
| 【2】 Chu, D.T.W.; Li, Q.; Claiborne, A.; et al.; Synthesis and antibacterial activity of A-86719.1 and related 2-pyridones: A novel series of potent DNA gyrase inhibitors. 34th Intersci Conf Antimicrob Agents Chemother (Oct 4-7, Orlando) 1994, Abst F41. |
| 【3】 Chu, D.T.; Li, Q.; Cooper, C.S.; Fung, A.K.L.; Lee, C.M.; Plattner, J.J. (Abbott Laboratories Inc.); Quinolizinone type cpds. JP 1997503783; WO 9510519 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 16819 | 3-chloro-2,4,5,6-tetrafluoropyridine; Pyridine, 3-chloro-2,4,5,6-tetrafluoro- | 1735-84-8 | C5ClF4N | 详情 | 详情 |
| (II) | 16820 | 4-(tert-butoxy)-3-chloro-2,5,6-trifluoropyridine; tert-butyl 3-chloro-2,5,6-trifluoro-4-pyridinyl ether | C9H9ClF3NO | 详情 | 详情 | |
| (III) | 16821 | 4-(tert-butoxy)-2,3,6-trifluoropyridine; tert-butyl 2,3,6-trifluoro-4-pyridinyl ether | C9H10F3NO | 详情 | 详情 | |
| (IV) | 16822 | tert-butyl 2,3,6-trifluoro-5-methyl-4-pyridinyl ether; 4-(tert-butoxy)-2,3,6-trifluoro-5-methylpyridine | C10H12F3NO | 详情 | 详情 | |
| (V) | 16823 | tert-butyl 2,5-difluoro-3-methyl-4-pyridinyl ether; 4-(tert-butoxy)-2,5-difluoro-3-methylpyridine | C10H13F2NO | 详情 | 详情 | |
| (VI) | 16824 | 2-cyclopropylacetonitrile; Cyclopropylacetonitrile | 6542-60-5 | C5H7N | 详情 | 详情 |
| (VII) | 16825 | 2-[4-(tert-butoxy)-5-fluoro-3-methyl-2-pyridinyl]-2-cyclopropylacetonitrile | C15H19FN2O | 详情 | 详情 | |
| (VIII) | 16826 | 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetonitrile | C11H10ClFN2 | 详情 | 详情 | |
| (IX) | 16827 | ethyl 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetate | C13H15ClFNO2 | 详情 | 详情 | |
| (X) | 16828 | 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetaldehyde | C11H11ClFNO | 详情 | 详情 | |
| (XI) | 16829 | Diethyl malonate | 105-53-3 | C7H12O4 | 详情 | 详情 |
| (XII) | 16830 | diethyl 2-[2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylethylidene]malonate | C18H21ClFNO4 | 详情 | 详情 | |
| (XIII) | 16831 | ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate | C16H15ClFNO3 | 详情 | 详情 | |
| (XIV) | 11685 | tert-butyl N-[(3S)tetrahydro-1H-pyrrol-3-yl]carbamate | C9H18N2O2 | 详情 | 详情 | |
| (XV) | 16833 | ethyl 8-[(3S)-3-[(tert-butoxycarbonyl)amino]tetrahydro-1H-pyrrol-1-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate | C25H32FN3O5 | 详情 | 详情 | |
| (XVI) | 16834 | 8-[(3S)-3-[(tert-butoxycarbonyl)amino]tetrahydro-1H-pyrrol-1-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid | C23H28FN3O5 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(VI)The reaction of 3-chlorotetrafluoropyridine (I) with potassium tert-butoxide in THF gives the 4-tert-butoxypyridine (II), which is dechlorinated with H2 over Pearlman's catalyst in methanol yielding 4-tert-butoxy-2,3,6-trifluoropyridine (III). The methylation of (III) with methyl iodide and LDA in THF affords the 5-methyl derivative (IV), which is partially defluorinated with hydrazine in refluxing propanol to provide 4-tert-butoxy-2,5-difluoro-3-methylpyridine (V). The condensation of (V) with cyclopropylacetonitrile (VI) by means of LDA in THF gives the alpha substituted acetonitrile (VII), which is treated with trifluoroacetic acid yielding the phenol (VIII). The reaction of (VIII) with POCl3 in dichloromethane/DMF affords the corresponding chloro derivative (IX), which is treated with dry HCl in ethanol giving the carboxylic ester (X). The reduction of (X) with LiAlH4 in THF affords the expected aldehyde (XI), which is cyclized with diethyl malonate, piperidine and acetic acid in refluxing ethanol giving the quinolizine carboxylate (XIII). The reaction of (XIII) with (1S,6S)-2-(tert-butoxycarbonyl)-2,8-diazabicyclo[4.3.0]nonane (XIV) by means of NaHCO3 in refluxing acetonitrile yields the condensation product (XV), which is saponified with LiOH in THF/wter providing the protcted target compound (XVI). Finally, this compound is deprotected with HCl in dioxane/methylene chloride.
| 【1】 Chu, D.T.; Li, Q.; Cooper, C.S.; Fung, A.K.L.; Lee, C.M.; Plattner, J.J.; Ma, Z.; Wang, W.-B. (Abbott Laboratories Inc.); Quinolizinone type cpds.. EP 0871628; JP 1999510478; WO 9639407 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 16819 | 3-chloro-2,4,5,6-tetrafluoropyridine; Pyridine, 3-chloro-2,4,5,6-tetrafluoro- | 1735-84-8 | C5ClF4N | 详情 | 详情 |
| (II) | 16820 | 4-(tert-butoxy)-3-chloro-2,5,6-trifluoropyridine; tert-butyl 3-chloro-2,5,6-trifluoro-4-pyridinyl ether | C9H9ClF3NO | 详情 | 详情 | |
| (III) | 16821 | 4-(tert-butoxy)-2,3,6-trifluoropyridine; tert-butyl 2,3,6-trifluoro-4-pyridinyl ether | C9H10F3NO | 详情 | 详情 | |
| (IV) | 16822 | tert-butyl 2,3,6-trifluoro-5-methyl-4-pyridinyl ether; 4-(tert-butoxy)-2,3,6-trifluoro-5-methylpyridine | C10H12F3NO | 详情 | 详情 | |
| (V) | 16823 | tert-butyl 2,5-difluoro-3-methyl-4-pyridinyl ether; 4-(tert-butoxy)-2,5-difluoro-3-methylpyridine | C10H13F2NO | 详情 | 详情 | |
| (VI) | 16824 | 2-cyclopropylacetonitrile; Cyclopropylacetonitrile | 6542-60-5 | C5H7N | 详情 | 详情 |
| (VII) | 16825 | 2-[4-(tert-butoxy)-5-fluoro-3-methyl-2-pyridinyl]-2-cyclopropylacetonitrile | C15H19FN2O | 详情 | 详情 | |
| (VIII) | 27200 | 2-cyclopropyl-2-(5-fluoro-4-hydroxy-3-methyl-2-pyridinyl)acetonitrile | C11H11FN2O | 详情 | 详情 | |
| (IX) | 16826 | 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetonitrile | C11H10ClFN2 | 详情 | 详情 | |
| (X) | 16827 | ethyl 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetate | C13H15ClFNO2 | 详情 | 详情 | |
| (XI) | 16828 | 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetaldehyde | C11H11ClFNO | 详情 | 详情 | |
| (XII) | 16829 | Diethyl malonate | 105-53-3 | C7H12O4 | 详情 | 详情 |
| (XIII) | 16831 | ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate | C16H15ClFNO3 | 详情 | 详情 | |
| (XIV) | 27201 | tert-butyl (4aS,7aS)octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate | C12H22N2O2 | 详情 | 详情 | |
| (XV) | 27202 | ethyl 8-[(4aS,7aS)-1-(tert-butoxycarbonyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate | C28H36FN3O5 | 详情 | 详情 | |
| (XVI) | 27203 | 8-[(4aS,7aS)-1-(tert-butoxycarbonyl)octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid | C26H32FN3O5 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(VII)Treatment of a commercial mixture of 4-chloro-tetrafluropyridine (I) and 3-chlorotetrafluoropyridine (II) with sodium tert-butoxide, followed by chromatographic separation, afforded 4-tert-butoxy-3-chloro-2,5,6-trifluoropyridine (III). Subsequent hydrogenolysis of the chlorine atom of (III) provided (IV), which was methylated with iodomethane in the presence of LDA yielding methylpyridine (V). Selective removal of the 6-fluorine of (V) to give (VI) was achieved by treatment with hydrazine hydrate in boiling n-propanol, followed by air oxidation of the intermediate pyridyl hydrazine. Alkylation of cyclopropaneacetonitrile (VII) with (VI) furnished the pyridinyl cyclopropaneacetonitrile (VIII). After acid cleavage of the tert-butyl group of (VIII), treatment with phosphoryl chloride in DMF gave rise to 4-chloropyridine derivative (IX). Then, alcoholysis of the cyano group of (IX) produced ethyl ester (X). Ester reduction by means of LiAlH4 and subsequent Swern oxidation of the resulting alcohol (XI) provided aldehyde (XII). The required quinolizinone system (XIII) was prepared by Knoevenagel condensation of pyridine aldehyde (XII) with diethyl malonate (1). The chiral piperidine (XV) was obtained by chiral HPLC resolution of racemic cis-N-carbobenzoxy-3-(tert-butoxycarbonylamino)-4-methylpiperidine (XIV), followed by hydrogenolytic cleavage of the carbobenzoxy group. Aromatic substitution of chloroquinolizinone (XIII) with piperidine (XV) yielded adduct (XVI). Hydrolysis of the ethyl ester of (XVI) with LiOH and further acid deprotection of the Boc group furnished the title compound.
| 【1】 Wang, S.; Ma, Z.; Flamm, R.K.; Cooper, C.S.; Li, Q.; Nilius, J.D.; Chu, D.T.W.; Sun OR, Y.; Meulbroek, J.A.; Shen, L.L.; Fung, A.K.L.; Synthesis and antimicrobial activity of 4H-4-oxoquinolizine derivatives: Consequences of structural modification at the C-8 position. J Med Chem 1999, 42, 20, 4202. |
| 【2】 Chu, D.T.; Li, Q.; Cooper, C.S.; Fung, A.K.L.; Lee, C.M.; Plattner, J.J.; Ma, Z.; Wang, W.-B. (Abbott Laboratories Inc.); Quinolizinone type cpds.. EP 0871628; JP 1999510478; WO 9639407 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 16829 | Diethyl malonate | 105-53-3 | C7H12O4 | 详情 | 详情 |
| (I) | 40621 | 4-chloro-2,3,5,6-tetrafluoropyridine | C5ClF4N | 详情 | 详情 | |
| (II) | 16819 | 3-chloro-2,4,5,6-tetrafluoropyridine; Pyridine, 3-chloro-2,4,5,6-tetrafluoro- | 1735-84-8 | C5ClF4N | 详情 | 详情 |
| (III) | 16820 | 4-(tert-butoxy)-3-chloro-2,5,6-trifluoropyridine; tert-butyl 3-chloro-2,5,6-trifluoro-4-pyridinyl ether | C9H9ClF3NO | 详情 | 详情 | |
| (IV) | 16821 | 4-(tert-butoxy)-2,3,6-trifluoropyridine; tert-butyl 2,3,6-trifluoro-4-pyridinyl ether | C9H10F3NO | 详情 | 详情 | |
| (V) | 16822 | tert-butyl 2,3,6-trifluoro-5-methyl-4-pyridinyl ether; 4-(tert-butoxy)-2,3,6-trifluoro-5-methylpyridine | C10H12F3NO | 详情 | 详情 | |
| (VI) | 16823 | tert-butyl 2,5-difluoro-3-methyl-4-pyridinyl ether; 4-(tert-butoxy)-2,5-difluoro-3-methylpyridine | C10H13F2NO | 详情 | 详情 | |
| (VII) | 16824 | 2-cyclopropylacetonitrile; Cyclopropylacetonitrile | 6542-60-5 | C5H7N | 详情 | 详情 |
| (VIII) | 16825 | 2-[4-(tert-butoxy)-5-fluoro-3-methyl-2-pyridinyl]-2-cyclopropylacetonitrile | C15H19FN2O | 详情 | 详情 | |
| (IX) | 16826 | 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetonitrile | C11H10ClFN2 | 详情 | 详情 | |
| (X) | 16827 | ethyl 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetate | C13H15ClFNO2 | 详情 | 详情 | |
| (XI) | 31627 | 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropyl-1-ethanol | C11H13ClFNO | 详情 | 详情 | |
| (XII) | 16828 | 2-(4-chloro-5-fluoro-3-methyl-2-pyridinyl)-2-cyclopropylacetaldehyde | C11H11ClFNO | 详情 | 详情 | |
| (XIII) | 16831 | ethyl 8-chloro-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate | C16H15ClFNO3 | 详情 | 详情 | |
| (XIV) | 40623 | benzyl (3S,4S)-3-[(tert-butoxycarbonyl)amino]-4-methyl-1-piperidinecarboxylate | C19H28N2O4 | 详情 | 详情 | |
| (XV) | 40622 | tert-butyl (3S,4S)-4-methylpiperidinylcarbamate | C11H22N2O2 | 详情 | 详情 | |
| (XVI) | 40624 | ethyl 8-[(3S,4S)-3-[(tert-butoxycarbonyl)amino]-4-methylpiperidinyl]-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate | C27H36FN3O5 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(X)Condensation of cyclopropaneacetonitrile (X) with bis(dimethylamino)-tert-butoxymethane gave rise to the enamino nitrile (XI). This was then cyclized with amidine (IX) to produce the target pyrimidine derivative.
| 【1】 Starub, A.; et al.; NO-independent stimulators of soluble guanylate cyclase. Bioorg Med Chem Lett 2001, 11, 6, 781. |
| 【2】 Feurer, A.; Stahl, E.; Stasch, J.-P.; Straub, A.; Dembowsky, K.; Alonso-Alija, C.; Perzborn, E.; Hutter, J. (Bayer AG); Substd. pyrazole derivs.. DE 19834047; EP 1102767; WO 0006568 . |
合成路线5
该中间体在本合成路线中的序号：(X)In a related method, Claisen condensation of ethyl formate with cyclopropaneacetonitrile (X), followed by acetylation of the intermediate potassium enolate (XII) with Ac2O, furnished the (acetoxy)acrylonitrile (XIII). This was finally cyclized with amidine (IX) in the presence of Et3N in refluxing toluene.
| 【1】 Straub, A.; Alonso-Alija, C.; Preiss, M.; Janichen, J. (Bayer AG); Method for the production of substd. pyrimidine derivs.. DE 19942809; WO 0117998 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IX) | 50477 | 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide | 256376-68-8 | C14H12FN5 | 详情 | 详情 |
| (X) | 16824 | 2-cyclopropylacetonitrile; Cyclopropylacetonitrile | 6542-60-5 | C5H7N | 详情 | 详情 |
| (XII) | 50479 | potassium (E)-2-cyano-2-cyclopropyl-1-ethenolate | C6H6KNO | 详情 | 详情 | |
| (XIII) | 50480 | (E)-2-cyano-2-cyclopropylethenyl acetate | C8H9NO2 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(I)The reaction of 2-cyclopropylacetonitrile (I) with ethyl formate (II) by means of t-BuOK in THF gives the hydroxymethylene derivative (III), which is cyclized with 1-(2-fluorobenzyl)pyrazolo[3,4-b]pyridine-3-carboxamidine (IV)(see scheme no. 28591301a, intermediate (IX)) by heating at 105 C to afford the target aminopyrimidine derivative.
| 【1】 Feurer, A.; et al.; 3-(2-Pyrimidinyl)pyrazolo[3,4-b]pyridines: A novel class of orally active NO-independent stimulators of soluble guanylate cyclase. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 205. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 16824 | 2-cyclopropylacetonitrile; Cyclopropylacetonitrile | 6542-60-5 | C5H7N | 详情 | 详情 |
| (II) | 45474 | methyl formate | 107-31-3 | C2H4O2 | 详情 | 详情 |
| (III) | 63160 | (Z)-2-cyclopropyl-3-hydroxy-2-propenenitrile | C6H7NO | 详情 | 详情 | |
| (IV) | 50477 | 1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine-3-carboximidamide | 256376-68-8 | C14H12FN5 | 详情 | 详情 |
合成路线7
该中间体在本合成路线中的序号：(III)4-Bromo-3-fluorotoluene (I) is converted into the Grignard reagent (II) with magnesium in boiling Et2O, and subsequently added to cyclopropylacetonitrile (III) to produce ketone (IV). Condensation of (IV) with hydroxylamine affords oxime (V), which is further alkylated with benzyl bromide to yield the O-benzyl oxime (VI). Asymmetric reduction of oxime (VI) with borane in the presence of the aminoalcohol chiral auxiliary (VII) provides the (S)-amine (VIII). Reaction of amine (VIII) with ammonium thiocyanate and benzoyl chloride, followed by treatment with hydrazine hydrate, gives rise to the thiourea (IX). Friedel-Crafts acylation of 4-chloro-2-methoxytoluene (X) with 2-bromopropionyl bromide (XI) employing AlCl3 furnishes the bromo ketone (XII). Then, condensation of thiourea (IX) with bromo ketone (XII) in the presence of Et3N in boiling EtOH gives rise to the aminothiazole (XIII). Finally, alkylation of the amino group of (XIII) with propargyl bromide (XIV) and NaH furnishes the title compound
| 【1】 Roger, P.; Gully, D.; Pradines, A.; Fontaine, E.; Geslin, M. (Sanofi-Synthelabo); Aminothiazole derivs. and their use as CRF receptor ligands. EP 1200419; FR 2796380; JP 2003505380; WO 0105776 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 60397 | 4-bromo-2-fluoro-1-methylbenzene | C7H6BrF | 详情 | 详情 | |
| (II) | 60398 | bromo(3-fluoro-4-methylphenyl)magnesium | C7H6BrFMg | 详情 | 详情 | |
| (III) | 16824 | 2-cyclopropylacetonitrile; Cyclopropylacetonitrile | 6542-60-5 | C5H7N | 详情 | 详情 |
| (IV) | 60399 | 2-cyclopropyl-1-(3-fluoro-4-methylphenyl)-1-ethanone | C12H13FO | 详情 | 详情 | |
| (V) | 60400 | 2-cyclopropyl-1-(3-fluoro-4-methylphenyl)-1-ethanone oxime | C12H14FNO | 详情 | 详情 | |
| (VI) | 60401 | 2-cyclopropyl-1-(3-fluoro-4-methylphenyl)-1-ethanone O-benzyloxime | C19H20FNO | 详情 | 详情 | |
| (VII) | 10103 | (2R)-2-Amino-3-methyl-1,1-diphenyl-1-butanol | 56755-20-5 (hydrochloride) | C17H21NO | 详情 | 详情 |
| (VIII) | 60402 | (1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)-1-ethanamine; (1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethylamine | C12H16FN | 详情 | 详情 | |
| (IX) | 60403 | N-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]thiourea | C13H17FN2S | 详情 | 详情 | |
| (X) | 60405 | 5-chloro-2-methylphenyl methyl ether; 4-chloro-2-methoxy-1-methylbenzene | C8H9ClO | 详情 | 详情 | |
| (XI) | 13127 | 2-Bromopropionyl bromide; 2-Bromopropanoyl bromide | 563-76-8 | C3H4Br2O | 详情 | 详情 |
| (XII) | 60404 | 2-bromo-1-(2-chloro-4-methoxy-5-methylphenyl)-1-propanone | C11H12BrClO2 | 详情 | 详情 | |
| (XIII) | 60406 | 4-(2-chloro-4-methoxy-5-methylphenyl)-N-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-1,3-thiazol-2-amine; N-[4-(2-chloro-4-methoxy-5-methylphenyl)-5-methyl-1,3-thiazol-2-yl]-N-[(1S)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]amine | C24H26ClFN2OS | 详情 | 详情 | |
| (XIV) | 23634 | acetylene | 74-86-2 | C2H2 | 详情 | 详情 |