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【结 构 式】

【分子编号】68579

【品名】(4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide

【CA登记号】 

【 分 子 式 】C27H25F2N3O5

【 分 子 量 】509.51

【元素组成】C 63.65% H 4.95% F 7.46% N 8.25% O 15.70%

与该中间体有关的原料药合成路线共 5 条

合成路线1

该中间体在本合成路线中的序号:(XV)

Protection of 3-hydroxy-2-methylpyran-4-one (I) with PhCH2Br in the presence of K2CO3 in acetonitrile at 80 °C or in DMF yields 3-(benzyloxy)-2-methylpyran-4-one (II) , which, after deprotonation with LiHMDS in THF, is condensed with benzaldehyde (III) at –60 °C to afford 3-(benzyloxy)-2-(2-hydroxy-2-phenylethyl) pyran-4-one (IV). Sulfonylation of alcohol (IV) with MsCl and Et3N in THF followed by mesylate elimination by means of DBU in NMP gives alkene (V), which by oxidative cleavage with NaIO4 in the presence of RuCl3, optionally using H2S, in acetonitrile/AcOEt/water, and further oxidation of the obtained aldehyde with NaClO2 or NaClO in the presence of TEMPO, yields the pyrancarboxylic acid (VI). Condensation of the 4-pyranone (VI) with 3-aminopropane-1,2-diol (VII) in EtOH at 80 °C leads to the pyridone (VIII), which is then converted to the methyl ester (IX) using MeI and NaHCO3. Oxidative cleavage of the vicinal diol (IX) with NaIO4 and AcOH or H2SO4 in acetonitrile/water provides the pyridone-1-acetaldehyde hydrate (X), which by cyclization with 3(R)-amino-1-butanol (XI) by means of AcOH in MeOH at 90 °C or diglyme yields the pyrido[1’,2’:4,5]pyrazino[2,1-b][1,3]oxazine derivative (XII). Bromination of compound (XII) with NBS in CH2Cl2 or NMP furnishes the bromopyridone derivative (XIII), which undergoes carbonylation with CO in the presence of 2,4-difluorobenzylamine (XIV) and Pd(PPh3)4/DIEA or Pd(OAc)2/DIEA/DPPB in DMSO at 90 °C to afford carboxamide (XV). Finally, compound (XV) is deprotected by debenzylation with H2 over Pd/C .
The pyrancarboxylic acid (VI) can also be prepared by oxidation of 3-(benzyloxy)-2-methylpyran-4-one (XVI) with SeO2 in bromobenzene at 160 °C to give aldehyde (XVII) and further oxidation with NaClO2 in the presence of NH2SO3H in acetone/H2O .

1 Johns, B.A., Duan, M., Hakogi, T. (Shionogi & Co., Ltd.; GlaxoSmithKline, Inc.). Processes and intermediates for carbamoylpyridone HIV integrase inhibitors. CN 102245572, EP 2376453, JP 2012511574, KR 2011096574, US 2011263855, WO 2010068262.
2 Yoshida, H., Taoda, Y., Johns, B.A. (Shionogi & Co., Ltd.; GlaxoSmithKline, Inc.). Synthesis of carbamoylpyridone HIV integrase inhibitors and intermediates. CN 102245182, EP 2376080, JP 012511573, KR 2011094336, US 2011282055, WO 2010068253.
3 Johns, B.A., Kawasuji, T., Taishi, T., Taoda, Y. (Shionogi & Co., Ltd.). Polycyclic carbamoylpyridone derivative having HIV integrase inhibitory activity. EP 1874117, EP 2465580, JP 2008540343, JP 2009079058, US 200931821, US 8129385, US 2012115875, WO 2006116764.
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) 13671 Hydroxymethylpyrone; 3-Hydroxy-2-methyl-4H-pyran-4-one;Maltol;3-Hydroxy-2-methyl-4-pyrone 118-71-8 C6H6O3 详情 详情
(II) 12074 3-(Benzyloxy)-2-methyl-4H-pyran-4-one;3-(benzyloxy)-2-methylpyran-4-one 61049-69-2 C13H12O3 详情 详情
(III) 10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(IV) 68571 3-(benzyloxy)-2-(2-hydroxy-2-phenylethyl)-4H-pyran-4-one   C20H18O4 详情 详情
(V) 68572 (E)-3-(benzyloxy)-2-styryl-4H-pyran-4-one   C20H16O3 详情 详情
(VI) 68573 3-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid   C13H10O5 详情 详情
(VII) 12979 3-Amino-1,2-propanediol;3-aminopropane-1,2-diol 616-30-8 C3H9NO2 详情 详情
(VIII) 68574 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylic acid   C16H17NO6 详情 详情
(IX) 68575 methyl 3-(benzyloxy)-1-(2,3-dihydroxypropyl)-4-oxo-1,4-dihydropyridine-2-carboxylate   C17H19NO6 详情 详情
(X) 68576 methyl 3-(benzyloxy)-1-(2,2-dihydroxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate   C16H17NO6 详情 详情
(XI) 68577 3(R)-amino-1-butanol;(R)-3-aminobutan-1-ol 61477-39-2 C4H11NO 详情 详情
(XII) 68581 (4R,12aS)-7-(benzyloxy)-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-6,8-dione   C19H20N2O4 详情 详情
(XIII) 68580 (4R,12aS)-7-(benzyloxy)-9-bromo-4-methyl-3,4,12,12a-tetrahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-6,8-dione   C19H19BrN2O4 详情 详情
(XIV) 68578 2,4-difluorobenzylamine 72235-52-0 C7H7F2N 详情 详情
(XV) 68579 (4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide   C27H25F2N3O5 详情 详情
(XVI) 12074 3-(Benzyloxy)-2-methyl-4H-pyran-4-one;3-(benzyloxy)-2-methylpyran-4-one 61049-69-2 C13H12O3 详情 详情
(XVII) 68582 3-(benzyloxy)-4-oxo-4H-pyran-2-carbaldehyde   C13H10O4 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XV)

Condensation of ethyl 3-(dimethylamino)acrylate (XVIII) with (benzyloxy)acetyl chloride (XIX) by means of pyridine in CH2Cl2 gives ethyl 2-[(benzyloxy)acetyl]-3-(dimethylamino)-2-propenoate (XX), which by cyclocondensation with ethyl oxalyl chloride (XXI) in the presence of LiHMDS in THF at –78 °C followed by heating with NH4OAc and AcOH affords pyridone derivative (XXII). Alkylation of pyridone (XXII) with bromoacetaldehyde dimethyl acetal (XXIII) and Cs2CO3 in DMF yields diethyl 1-(2,2-dimethoxyethyl)-3-(benzyloxy)-1,4-dihydropyridine-2,5-dicarboxylate (XXIV), which can also be obtained by condensation of diethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-dicarboxylate (XXV) with 2,2-dimethoxyethylamine (XXVI) in EtOH. Hydrolysis of acetal (XXIV) with H2SO4 and HCOOH in CH2Cl2 yields aldehyde (XXVII), which upon cyclocondensation with 3(R)-amino-1-butanol (XI) by means of AcOH in refluxing MeOH/toluene provides the hexahydropyrido[1’,2’:4,5]pyrazino[2,1-b][1,3]oxazine derivative (XXVIII). Hydrolysis of ester (XXVIII) with NaOH in THF/MeOH/H2O gives the corresponding free acid (XXIX), which is finally condensed with 2,4-difluorobenzylamine (XIV) in the presence of HATU and NMM in DMF .
Propenoate (XX) can also be prepared by condensation of ethyl 4-chloroacetoacetate (XXX) with PhCH2OH in the presence of t-AmONa to give benzyl ether (XXXI), which then reacts with N,N-dimethylformamide dimethyl acetal (XXXII) in toluene .

1 Sumino, Y., Okamoto, K., Masui, M., Yamada, D., Ikarashi, F. (Shionogi & Co., Ltd.). Process for preparing compound having HIV integrase inhibitory activity. WO 2012018065.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 68577 3(R)-amino-1-butanol;(R)-3-aminobutan-1-ol 61477-39-2 C4H11NO 详情 详情
(XIV) 68578 2,4-difluorobenzylamine 72235-52-0 C7H7F2N 详情 详情
(XV) 68579 (4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide   C27H25F2N3O5 详情 详情
(XVIII) 16000 ethyl (E)-3-(dimethylamino)-2-propenoate; Ethyl trans-3-dimethylaminoacrylate 1117-37-9 C7H13NO2 详情 详情
(XIX) 10493 2-(Benzyloxy)acetyl chloride; Benzyloxyacetyl chloride 19810-31-2 C9H9ClO2 详情 详情
(XX) 68583 (E)-ethyl 4-(benzyloxy)-2-((dimethylamino)methylene)-3-oxobutanoate   C16H21NO4 详情 详情
(XXI) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(XXII) 68584 diethyl 3-(benzyloxy)-4-oxo-1,4-dihydropyridine-2,5-dicarboxylate   C18H19NO6 详情 详情
(XXIII) 13183 2-Bromo-1,1-dimethoxyethane; 2-Bromo-1-methoxyethyl methyl ether; Bromoacetaldehyde dimethyl acetal 7252-83-7 C4H9BrO2 详情 详情
(XXIV) 68585 1-(2,2-dimethoxyethyl)-3-(benzyloxy)-1,4-dihydropyridine-2,5-dicarboxylate diethyl;diethyl 3-(benzyloxy)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2,5-dicarboxylate   C22H27NO8 详情 详情
(XXV) 68586 diethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-dicarboxylate   C18H18O7 详情 详情
(XXVI) 34158 aminoacetaldehyde dimethylacetal; 2,2-dimethoxy-1-ethanamine; 2,2-dimethoxyethylamine 22483-09-6 C4H11NO2 详情 详情
(XXVII) 68587 diethyl 3-(benzyloxy)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2,5-dicarboxylate   C20H21NO7 详情 详情
(XXVIII) 68588 (4R,12aS)-ethyl 7-(benzyloxy)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylate   C22H24N2O6 详情 详情
(XXIX) 68589 (4R,12aS)-7-(benzyloxy)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylic acid   C20H20N2O6 详情 详情
(XXX) 23541 ethyl 4-chloro-3-oxobutanoate;Ethyl 4-chloro-3-oxobutanoate;Ethyl 4-chloroacetoacetate 638-07-3 C6H9ClO3 详情 详情
(XXXI) 68590 ethyl 4-(benzyloxy)-3-oxobutanoate   C13H16O4 详情 详情
(XXXII) 11984 N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine; Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal 4637-24-5 C5H13NO2 详情 详情

合成路线3

该中间体在本合成路线中的序号:(XV)

Condensation of methyl 4-chloroacetoacetate (XXXIII) with PhCH2OH in the presence of t-AmONa in THF gives the benzyl ether (XXXIV), which is then condensed with N,N-dimethylformamide dimethyl acetal (XXXII) in dioxane to give methyl 2-[(benzyloxy) acetyl]-3-aminoacrylate (XXXV). Cyclocondensation of acrylate (XXXV) with dimethyl oxalate by means of t-BuONa provides the pyranone derivative (XXXVII), which is then reacted with aminoacetaldehyde dimethyl acetal (XXVI) at reflux to yield pyridone (XXXVIII). Hydrolysis of acetal (XXXVIII) with H2SO4 and HCOOH affords aldehyde (XXXIX), which upon cyclocondensation with 3(R)-amino-1-butanol (XI) in the presence of AcOH in refluxing MeOH/toluene gives the hexahydropyrido[1’,2’:4,5]pyrazino[2,1-b][1,3]oxazine derivative (XL). Finally, methyl ester (XL) is condensed with 2,4-difluorobenzylamine (XIV) in the presence of AcOH in toluene .
Alternatively, coupling of methyl ester (XXXVIII) with 2,4-difluorobenzylamine (XIV) by means of AcOH in toluene/MeOH gives amide (XLI), which upon acetal hydrolysis with H2SO4 and HCOOH in toluene yields aldehyde (XLII). Finally, aldehyde (XLII) is submitted to cyclocondensation with 3(R)-amino-1-butanol (XI) in the presence of AcOH in refluxing MeOH/toluene .

1 Sumino, Y., Okamoto, K., Masui, M., Yamada, D., Ikarashi, F. (Shionogi & Co., Ltd.). Process for preparing compound having HIV integrase inhibitory activity. WO 2012018065.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XL) 68597 (4R,12aS)-methyl 7-(benzyloxy)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylate   C21H22N2O6 详情 详情
(XI) 68577 3(R)-amino-1-butanol;(R)-3-aminobutan-1-ol 61477-39-2 C4H11NO 详情 详情
(XIV) 68578 2,4-difluorobenzylamine 72235-52-0 C7H7F2N 详情 详情
(XV) 68579 (4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide   C27H25F2N3O5 详情 详情
(XXVI) 34158 aminoacetaldehyde dimethylacetal; 2,2-dimethoxy-1-ethanamine; 2,2-dimethoxyethylamine 22483-09-6 C4H11NO2 详情 详情
(XXXII) 11984 N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine; Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal 4637-24-5 C5H13NO2 详情 详情
(XXXIII) 68591 methyl 4-chloro-3-oxobutanoate;Methyl 4-chloro-3-oxo-butanoate;Methyl 4-chloro-3-oxobutyrate;Methyl 4-chloroacetoacetate 32807-28-6 C5H7ClO3 详情 详情
(XXXIV) 68592 methyl 4-(benzyloxy)-3-oxobutanoate   C12H14O4 详情 详情
(XXXV) 68593 (E)-methyl 4-(benzyloxy)-2-((dimethylamino)methylene)-3-oxobutanoate;methyl 2-[(benzyloxy)acetyl]-3-aminoacrylate   C15H19NO4 详情 详情
(XXXVI) 37412 methyl 2-methoxy-2-oxoacetate;dimethyl oxalate;Methyl oxalate 553-90-2 C4H6O4 详情 详情
(XXXVII) 68594 dimethyl 3-(benzyloxy)-4-oxo-4H-pyran-2,5-dicarboxylate   C16H14O7 详情 详情
(XXXVIII) 68595 dimethyl 3-(benzyloxy)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2,5-dicarboxylate   C20H23NO8 详情 详情
(XXXIX) 68596 dimethyl 3-(benzyloxy)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2,5-dicarboxylate   C18H17NO7 详情 详情
(XLI) 68598 methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2-carboxylate   C26H26F2N2O7 详情 详情
(XLII) 68599 methyl 3-(benzyloxy)-5-((2,4-difluorobenzyl)carbamoyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2-carboxylate   C24H20F2N2O6 详情 详情

合成路线4

该中间体在本合成路线中的序号:(XV)

Condensation of methyl 4-methoxyacetoacetate (XLIII) with N,N-dimethylformamide dimethyl acetal (XXXII) produces methyl 3-(dimethylamino)-2-(methoxyacetyl)-2-propenoate (XLIV), which by reaction with 2,2-dimethoxyethylamine (XXVI) in MeOH affords the N-(dimethyoxyethyl)enamine (XLV). Cyclization of enaminoketone (XLV) with dimethyl oxalate (XXXVI) by means of LiH at 40 °C gives the dimethyl pyridone-dicarboxylate (XLVI), which by selective hydrolysis with LiOH yields the monocarboxylic acid (XLVII). Hydrolysis of acetal (XLVII) with MsOH and AcOH in acetonitrile at 58-65 °C followed by in situ cyclization of the resulting aldehyde (XLVIII) with 3(R)-amino-1-butanol (XI) in acetonitrile at 64 °C affords the pyrido[1’,2’:4,5]pyrazino[2,1-b][1,3]oxazine derivative (XLIX). Activation of acid (XLIX) with CDI in DME at 80 °C and subsequent coupling with 2,4-difluorobenzylamine (XIV) gives amide (L), which is finally O-demethylated with either MgBr2 in hot acetonitrile or LiBr in refluxing THF .

1 Wang, H., Goodman, S.N., Mans, D., Kowalski, M. (GlaxoSmithKline, Inc.). Process for preparing carbamoylpyridone derivatives and intermediates. WO 2011119566.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 68577 3(R)-amino-1-butanol;(R)-3-aminobutan-1-ol 61477-39-2 C4H11NO 详情 详情
(XIV) 68578 2,4-difluorobenzylamine 72235-52-0 C7H7F2N 详情 详情
(XV) 68579 (4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide   C27H25F2N3O5 详情 详情
(XXVI) 34158 aminoacetaldehyde dimethylacetal; 2,2-dimethoxy-1-ethanamine; 2,2-dimethoxyethylamine 22483-09-6 C4H11NO2 详情 详情
(XXXII) 11984 N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine; Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal 4637-24-5 C5H13NO2 详情 详情
(XXXVI) 37412 methyl 2-methoxy-2-oxoacetate;dimethyl oxalate;Methyl oxalate 553-90-2 C4H6O4 详情 详情
(XLIII) 26655 methyl 4-methoxy-3-oxobutanoate;Methyl 4-methoxyacetoacetate;Methyl 4-methoxy-3-oxo-butanoate 41051-15-4 C6H10O4 详情 详情
(XLIV) 68600 methyl 3-(dimethylamino)-2-(methoxyacetyl)-2-propenoate;(Z)-methyl 2-((dimethylamino)methylene)-4-methoxy-3-oxobutanoate   C9H15NO4 详情 详情
(XLV) 68601 (Z)-methyl 2-(((2,2-dimethoxyethyl)amino)methylene)-4-methoxy-3-oxobutanoate   C11H19NO6 详情 详情
(XLVI) 68602 dimethyl 1-(2,2-dimethoxyethyl)-3-methoxy-4-oxo-1,4-dihydropyridine-2,5-dicarboxylate   C14H19NO8 详情 详情
(XLVII) 68603 1-(2,2-dimethoxyethyl)-5-methoxy-6-(methoxycarbonyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid   C13H17NO8 详情 详情
(XLVIII) 68604 5-methoxy-6-(methoxycarbonyl)-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-3-carboxylic acid   C11H11NO7 详情 详情
(XLIX) 68606 (4R,12aS)-7-methoxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylic acid   C14H16N2O6 详情 详情
(L) 68605 (4R,12aS)-N-(2,4-difluorobenzyl)-7-methoxy-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide   C21H21F2N3O5 详情 详情

合成路线5

该中间体在本合成路线中的序号:(XV)

Condensation of ethyl 4-chloro-3-oxobutyrate (XXX) with N,Ndimethylformamide dimethylacetal (XXXII) in EtOAc results in ethyl 2-(chloroacetyl)-3-(dimethylamino)-2-propenoate (LI), which by cyclocondensation with ethyl oxalyl chloride (XXI) by means of LiHMDS in THF affords diethyl 3-chloro-4-oxopyran-2,5-dicarboxylate (LII). Condensation of pyranone (LII) with 2,2-dimethoxyethylamine (XXVI) in EtOH gives pyridone (LIII), which is then hydrolyzed using HCOOH and H2SO4 in CH2Cl2 to yield the corresponding aldehyde (LIV). Cyclization of compound (LIV) with 3(R)-amino-1-butanol (XI) and AcOH in refluxing MeOH/toluene provides the hexahydropyrido[1’,2’:4,5]pyrazino[2,1-b][1,3]oxazine derivative (LV), which by hydrolysis with KOSiMe3 in DME affords the hydroxy acid (LVI). Finally, acid (LVI) is coupled with 2,4-difluorobenzylamine (XIV) in the presence of HATU and NMM in DMF .

1 Sumino, Y., Okamoto, K., Masui, M., Yamada, D., Ikarashi, F. (Shionogi & Co., Ltd.). Process for preparing compound having HIV integrase inhibitory activity. WO 2012018065.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XI) 68577 3(R)-amino-1-butanol;(R)-3-aminobutan-1-ol 61477-39-2 C4H11NO 详情 详情
(XIV) 68578 2,4-difluorobenzylamine 72235-52-0 C7H7F2N 详情 详情
(XV) 68579 (4R,12aS)-7-(benzyloxy)-N-(2,4-difluorobenzyl)-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxamide   C27H25F2N3O5 详情 详情
(XXI) 11043 Ethyl 2-chloro-2-oxoacetate; Ethyl oxalyl chloride 4755-77-5 C4H5ClO3 详情 详情
(XXVI) 34158 aminoacetaldehyde dimethylacetal; 2,2-dimethoxy-1-ethanamine; 2,2-dimethoxyethylamine 22483-09-6 C4H11NO2 详情 详情
(XXX) 23541 ethyl 4-chloro-3-oxobutanoate;Ethyl 4-chloro-3-oxobutanoate;Ethyl 4-chloroacetoacetate 638-07-3 C6H9ClO3 详情 详情
(XXXII) 11984 N-(Dimethoxymethyl)-N,N-dimethylamine;dimethylformamide dimethylacetal;1,1-dimethoxy-N,N-dimethylmethanamine; Dimethoxy-N,N-dimethylmethanamine; N,N-Dimethylformamide dimethyl acetal 4637-24-5 C5H13NO2 详情 详情
(LI) 68607 ethyl 2-(chloroacetyl)-3-(dimethylamino)-2- propenoate;(E)-ethyl 4-chloro-2-((dimethylamino)methylene)-3-oxobutanoate   C9H14ClNO3 详情 详情
(LII) 68608 diethyl 3-chloro-4-oxo-4H-pyran-2,5-dicarboxylate   C11H11ClO6 详情 详情
(LIII) 68609 diethyl 3-chloro-1-(2,2-dimethoxyethyl)-4-oxo-1,4-dihydropyridine-2,5-dicarboxylate   C15H20ClNO7 详情 详情
(LIV) 68610 diethyl 3-chloro-4-oxo-1-(2-oxoethyl)-1,4-dihydropyridine-2,5-dicarboxylate   C13H14ClNO6 详情 详情
(LV) 68612 (4R,12aS)-ethyl 7-chloro-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylate   C15H17ClN2O5 详情 详情
(LVI) 68611 (4R,12aS)-7-chloro-4-methyl-6,8-dioxo-3,4,6,8,12,12a-hexahydro-2H-pyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazine-9-carboxylic acid   C13H13ClN2O5 详情 详情
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