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【结 构 式】 
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【分子编号】60046 【品名】4-chloro-7H-pyrrolo[2,3-d]pyrimidine；6-Chloro-7-deazapurine；4-chloropyrrolo[2,3-d]pyrimidine；4-Chloro-1H-pyrrolo[2,3-d]pyrimidine 【CA登记号】3680-69-1 |
【 分 子 式 】C6H4ClN3 【 分 子 量 】153.57068 【元素组成】C 46.93% H 2.63% Cl 23.09% N 27.36% |
合成路线1
该中间体在本合成路线中的序号：(III)Racemic CP-690550 can be obtained by the following method. Reductive amination of 1-benzyl-4-methylpiperidin-3-one (I) with methylamine and sodium triacetoxyborohydride in THF gives N-methyl-1-benzyl-4-methylpiperidin-3-amine (II), which is condensed with 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (III) by means of triethylamine in a sealed tube at 100 °C to yield the tertiary amine (IV). After deprotection of (IV) by catalytic hydrogenolysis over Pd(OH)2/C, the debenzylated piperidine (V) is acylated with cyanoacetyl chloride (VI) and pyridine in CH2Cl2 to provide the target compound (1). Scheme 1.
| 【1】 Blumenkopf, T.A., Flanagan, M.E., Munchhof, M.J. (Pfizer Products Inc.). Pyrrolo[2,3-d]pyrimidine cpds. EP 1235830, JP 2003516405, US 2001053782, US 6627754, WO 0142246. |
| 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) | 65390 | 1-benzyl-4-methylpiperidin-3-one | C12H17NO | 详情 | 详情 | |
| (II) | 65391 | 1-Benzyl-N,4-dimethylpiperidin-3-amine; (1-Benzyl-4-methylpiperidin-3-yl)methylamine | 384338-23-2 | C14H22N2 | 详情 | 详情 |
| (III) | 60046 | 4-chloro-7H-pyrrolo[2,3-d]pyrimidine；6-Chloro-7-deazapurine；4-chloropyrrolo[2,3-d]pyrimidine；4-Chloro-1H-pyrrolo[2,3-d]pyrimidine | 3680-69-1 | C6H4ClN3 | 详情 | 详情 |
| (IV) | 65392 | N-Methyl-N-[(3RS,4RS)-4-methyl-1-(phenylmethyl)-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine | C20H25N5 | 详情 | 详情 | |
| (V) | 65393 | N-Methyl-N-[(3RS,4RS)-4-methyl-3-piperidinyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine | C13H19N5 | 详情 | 详情 | |
| (VI) | 65394 | cyanoacetyl chloride | C3H2ClNO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(IV)Condensation of cyano ester (I) with formamidine in the presence of NaOEt afforded the pyrimidinone derivative (II). Acetal hydrolysis of (II) with concomitant intramolecular cyclization under acidic conditions produced the pyrrolopyrimidinone (III), which was further chlorinated to (IV) in refluxing POCl3. Displacement of the 4-chloro of (IV) with 3-chloro-4-fluoroaniline (V) in the presence of silver triflate in hot DMF afforded the anilino pyrrolopyrimidine (VI). Oxidation of (VI) using pyridinium bromide perbromide furnished the alpha,alpha-dibromo lactam (VII). Reductive debromination of (VII) by means of zinc dust in AcOH gave intermediate (VIII).
| 【1】 Wei, C.C.; Tang, P.C.; McMahon, G.; Sun, L.; Hirth, K.P.; Liang, C.; Cui, J. (Sugen, Inc.); 4-Substd. 7-aza-indolin-2-ones and their use as protein kinase inhibitors. EP 1244672; WO 0146196 . |
| 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) | 14789 | ethyl 2-cyano-4,4-diethoxybutanoate | C11H19NO4 | 详情 | 详情 | |
| (II) | 60644 | 2-[4-bromo-2-(2-fluorobenzoyl)anilino]-2-oxoethyl 4-methylbenzenesulfonate | C22H17BrFNO5S | 详情 | 详情 | |
| (III) | 60045 | 3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one | C6H5N3O | 详情 | 详情 | |
| (IV) | 60046 | 4-chloro-7H-pyrrolo[2,3-d]pyrimidine；6-Chloro-7-deazapurine；4-chloropyrrolo[2,3-d]pyrimidine；4-Chloro-1H-pyrrolo[2,3-d]pyrimidine | 3680-69-1 | C6H4ClN3 | 详情 | 详情 |
| (V) | 18688 | 3-Chloro-4-fluorophenylamine; 3-Chloro-4-fluoroaniline | 367-21-5 | C6H5ClFN | 详情 | 详情 |
| (VI) | 60850 | N-(3-chloro-4-fluorophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine; N-(3-chloro-4-fluorophenyl)-N-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine | C12H8ClFN4 | 详情 | 详情 | |
| (VII) | 60851 | 5,5-dibromo-4-(3-chloro-4-fluoroanilino)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one | C12H6Br2ClFN4O | 详情 | 详情 | |
| (VIII) | 60852 | 4-(3-chloro-4-fluoroanilino)-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one | C12H8ClFN4O | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(V)Condensation of 2-cyano-4,4-diethoxybutyric acid ethyl ester (I) with formamidine hydrochloride (II) in the presence of NaOEt provides the pyrimidine derivative (III). Subsequent hydrolysis of the diethyl acetal of (III) under acidic conditions leads to the pyrrolopyrimidinone (IV). This is converted to the 4-chloro derivative (V) upon treatment with POCl3. Then, oxidation of (V) by means of pyridinium bromide perbromide furnishes the dibromo pyrrolopyridinone (VI), which is further debrominated to (VII) employing zinc dust in AcOH
| 【1】 Wei, C.C.; Tang, P.C.; McMahon, G.; Sun, L.; Hirth, K.P.; Liang, C.; Cui, J. (Sugen, Inc.); 4-Substd. 7-aza-indolin-2-ones and their use as protein kinase inhibitors. EP 1244672; WO 0146196 . |
| 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) | 14789 | ethyl 2-cyano-4,4-diethoxybutanoate | C11H19NO4 | 详情 | 详情 | |
| (II) | 15369 | Iminoformamide; Methanimidamide | 463-52-5 | CH4N2 | 详情 | 详情 |
| (III) | 60044 | 6-amino-5-(2,2-diethoxyethyl)-4(3H)-pyrimidinone | C10H17N3O3 | 详情 | 详情 | |
| (IV) | 60045 | 3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one | C6H5N3O | 详情 | 详情 | |
| (V) | 60046 | 4-chloro-7H-pyrrolo[2,3-d]pyrimidine；6-Chloro-7-deazapurine；4-chloropyrrolo[2,3-d]pyrimidine；4-Chloro-1H-pyrrolo[2,3-d]pyrimidine | 3680-69-1 | C6H4ClN3 | 详情 | 详情 |
| (VI) | 60047 | 5,5-dibromo-4-chloro-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one | C6H2Br2ClN3O | 详情 | 详情 | |
| (VII) | 60048 | 4-chloro-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one | C6H4ClN3O | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(I)N-Protection of 4-chloropyrrolo[2,3-d]pyrimidine (I) with POM-Cl by means of NaH in DME yields the POM-protected deazapurine (II), which is then subjected to Suzuki coupling with pinacol 1-(1-ethoxyethyl)-4-pyrazolylboronate (III) using K2CO3 and Pd(PPh3)4 in BuOH at 82 °C to give the protected pyrazolyl-deazapurine derivative (IV). Without isolation, compound (IV) is N-deprotected with HCl in THF, providing the pyrazole-deazapurine (V), which is then condensed with 2-[1-(ethylsulfonyl)azetidin-3-ylidene]acetonitrile (VI) in the presence of DBU in DMF to produce the 3-[1-(ethylsulfonyl)azetidin-3-yl]pyrazole derivative (VII). Finally, the POM protecting group is removed from precursor (VII) by means of NaOH in MeOH/THF or LiOH·H2O in acetonitrile/i-PrOH .
Coupling of SEM-protected deazapurine (VIII) with azetidine derivative (VI) in the presence of DBU in DMF affords the corresponding ethylsulfonyl derivative (IX), which is then N-deprotected by means of LiBF4 in acetonitrile/water and finally, without isolation, is reacted with NH4OH .
| 【1】 Rodgers, J.D., Shepard, S., Li, Y.-L., Zhou, J., Liu, P., Meloni, D., Xia, M.(Incyte Corp.). Azetidine and cyclobutane derivatives as JAK inhibitors. CN 102026999, EP 2288610, JP 2011514909, KR 2010121657, KR 2012108042, US 2009233903, US 2012077798, US 8158616, US 8420629, US 2013225556, WO 2009114512. |
| 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) | 60046 | 4-chloro-7H-pyrrolo[2,3-d]pyrimidine；6-Chloro-7-deazapurine；4-chloropyrrolo[2,3-d]pyrimidine；4-Chloro-1H-pyrrolo[2,3-d]pyrimidine | 3680-69-1 | C6H4ClN3 | 详情 | 详情 |
| (II) | 69168 | C6H3ClN3.POM | 详情 | 详情 | ||
| (III) | 68071 | 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | C13H23BN2O3 | 详情 | 详情 | |
| (V) | 69169 | C9H6N5.POM | 详情 | 详情 | ||
| (VI) | 68070 | 2-[1-(ethylsulfonyl)azetidin-3-ylidene]acetonitrile | C7H10N2O2S | 详情 | 详情 | |
| (VIII) | 68072 | 4-(1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine | C15H21N5OSi | 详情 | 详情 | |
| (IX) | 68073 | 2-(1-(ethylsulfonyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile | C22H31N7O3SSi | 详情 | 详情 | |
| (X) | 68074 | 2-(1-(ethylsulfonyl)-3-(4-(7-(hydroxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile | C17H19N7O3S | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(I)N-Protection of 4-chloropyrrolo[2,3-d]pyrimidine (I) by means of SEM-Cl in the presence of NaH in DMAc or DMF yields the protected deazapurine (XX) , which is then subjected to Suzuki coupling with pinacol 1-(1-ethoxyethyl)-4-pyrazolylboronate (III) in the presence of K2CO3 and Pd(PPh3)4 in BuOH to give the pyrazol-deazapurine derivative (XXI). Without isolation, compound (XXI) is N-deprotected by acidic hydrolysis to afford the SEM-protected deazapurine (VIII) . Alternatively, intermediate (VIII) can be obtained by Suzuki coupling of N-SEM-4-chloropyrrolo[2,3-d]pyrimidine (XX) with unprotected pyrazolylboronate (XXII) in the presence of K2CO3 and Pd(PPh3)4 in DMF at 125 °C . Coupling of SEM-protected deazapurine (VIII) with N-Boc-3-(cyanomethylene)azetidine (XVII) in the presence of DBU in acetonitrile affords the corresponding acetonitrile derivative (XXIII) , which is then N-deprotected by means of HCl in CH2Cl2 or 1,4-dioxane to provide the azetidine derivative (XXIV) . Finally, condensation of compound (XXIV) with ethanesulfonyl chloride (XIX) using DIEA in THF/EtOAc, followed by N-deprotection of the resulting adduct (IX) with TFA in CH2Cl2 affords baricitinib trifluoroacetate .
Alternatively, N,N-deprotection of intermediate (XXIII) with TFA in CH2Cl2, followed by condensation of the resulting imine (XXVI) with ethanesulfonyl chloride (XIX) using Et3N in THF also results in baricitinib trifluoroacetate .
| 【1】 Rodgers, J.D., Shepard, S., Li, Y.-L., Zhou, J., Liu, P., Meloni, D., Xia, M.(Incyte Corp.). Azetidine and cyclobutane derivatives as JAK inhibitors. CN 102026999, EP 2288610, JP 2011514909, KR 2010121657, KR 2012108042, US 2009233903, US 2012077798, US 8158616, US 8420629, US 2013225556, WO 2009114512. |
| 【2】 Friedman, P.A., Fridman, J.S., Luchi, M.E., Williams, W.V. (Incyte Corp.). Janus kinase inhibitors for treatment of dry eye and other eye related dis-eases. EP 2349260, JP 2012504639, US 201011416, US 2012301464, WO 2010039939. |
| 【3】 Rodgers, J.D., Shepard, S., Maduskuie, T.P. Jr. et al. (Incyte Corp.). Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as Janus kinase inhibitors. CA 2632466, EP 1966202, EP 2343298, EP 2343299, EP 2348023, EP 2426129, EP 2455382, EP 2474545, JP 2009519340, KR 2012120462, KR 2012120463, US 2007135461, US 7598257, WO 2007070514. |
| 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) | 60046 | 4-chloro-7H-pyrrolo[2,3-d]pyrimidine；6-Chloro-7-deazapurine；4-chloropyrrolo[2,3-d]pyrimidine；4-Chloro-1H-pyrrolo[2,3-d]pyrimidine | 3680-69-1 | C6H4ClN3 | 详情 | 详情 |
| (III) | 68071 | 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | C13H23BN2O3 | 详情 | 详情 | |
| (VIII) | 68072 | 4-(1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine | C15H21N5OSi | 详情 | 详情 | |
| (X) | 68074 | 2-(1-(ethylsulfonyl)-3-(4-(7-(hydroxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile | C17H19N7O3S | 详情 | 详情 | |
| (XVII) | 68077 | N-Boc-3-(cyanomethylene)azetidine | C10H14N2O2 | 详情 | 详情 | |
| (XIX) | 54065 | Ethanesulfonyl chloride; Ethylsulfonyl chloride | 594-44-5 | C2H5ClO2S | 详情 | 详情 |
| (XX) | 68079 | 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine | C12H18ClN3OSi | 详情 | 详情 | |
| (XXI) | 68080 | 4-(1-(1-ethoxyethyl)-1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine | C19H29N5O2Si | 详情 | 详情 | |
| (XXII) | 68081 | 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | C9H15BN2O2 | 详情 | 详情 | |
| (XXIII) | 68082 | tert-butyl 3-(cyanomethyl)-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate | C25H35N7O3Si | 详情 | 详情 | |
| (XXIV) | 68083 | 2-(3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile | C20H27N7OSi | 详情 | 详情 | |
| (XXVI) | 68084 | 2-(3-(4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)azetidin-3-yl)acetonitrile bis(2,2,2-trifluoroacetate) | C14H13N7.2C2HF3O2 | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(I)N-Protection of 4-chloropyrrolo[2,3-d]pyrimidine (I) with either 2-(trimethylsilyl) ethoxymethyl chloride (SEM-Cl) in DMA or pivaloyloxymethyl chloride (POM-Cl) in THF in the presence of NaH yields the protected deazapurines (IIa) and (IIb) , respectively, which by Suzuki coupling with pinacol 1-(1-ethoxyethyl)-4-pyrazolylboronate (III) by means of Pd(PPh3)4 and K2CO3, followed by acidic hydrolysis of the ethoxyethyl group, affords the respective pyrazolyl deazapurines (Va) and (Vb) . Alternatively, intermediate (Va) can be obtained by Suzuki coupling of deazapurine (IIa) with unprotected pyrazolylboronate (IV) by means of Pd(PPh3)4 and K2CO3 in DMF/H2O at 125 °C . Michael addition of pyrazole derivative (Va) to 3-cyclopentylacrylonitrile (VI) (obtained by Wittig condensation of cyclopentylcarboxaldehyde [VII] with diethyl cyanomethylphosphonate [VIII] by means of t-BuOK in THF) in the presence of DBU in acetonitrile, followed by resolution using chiral preparative HPLC, provides the desired (R)-adduct (IXa) . Alternatively, in an enantioselective procedure, asymmetric aza-Michael reaction of (Va) or (Vb) with (E)-3-cyclopentylacrylaldehyde (X) in the presence of p-nitrobenzoic acid (p-NBA) and a chiral diarylprolinol silyl ether in CHCl3 gives aldehydes (XIa) and (XIb), which by subsequent condensation with NH4OH, followed by oxidation of the intermediate imines with I2 in aqueous solution, leads to the corresponding nitriles (IXa) and (IXb) . Finally, ruxolitinib is obtained by deprotection of compound (IXa) by sequential treatment with LiBF4 in refluxing acetonitrile/H2O followed by aqueous NH4OH , or with TFA in CH2Cl2 and subsequent basification of obtained TFA salt with ethylenediamine (EDA) in MeOH , or by deprotection of compound (IXb) by treatment with NaOH in MeOH/H2O .
In an alternative strategy, ruxolitinib can be directly obtained by Suzuki coupling of unprotected 4-chloropyrrolo[2,3-d]pyrimidine (I) with the pyrazolylboronate (XII) in the presence of Pd(PPh3)4 and K2CO3 in 1,4-dioxane/H2O at 100 °C .
| 【1】 Lin, Q., Meloni, D., Pan, Y. et al. Enantioselective synthesis of Janus kinase inhibitor INCB018424 via an organocatalytic aza-Michael reaction. Org Lett 2009, 11(9): 1999-2002. |
| 【2】 Rodgers, J.D., Shepard, S., Maduskuie, T.P. Jr. et al. (Incyte Corp.). Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as Janus kinase inhibitors. US 20090181959. |
| 【3】 Rodgers, J.D., Shepard, S., Maduskuie, T.P. Jr. et al. (Incyte Corp.). Heteroaryl substituted pyrrolo[2,3-b]pyridines and pyrrolo[2,3-b]pyrimidines as Janus kinase inhibitors. CA 2632466, EP 1966202, JP 2009519340, US 2007135461, US 7598257, WO 2007070514. |
| 【4】 Friedman, P.A., Fridman, J.S., Luchi, M.E., Williams, W.V. (Incyte Corp.). Janus kinase inhibitors for treatment of dry eye and other eye related diseases. WO 2010039939. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IIa) | 68079 | 4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine | C12H18ClN3OSi | 详情 | 详情 | |
| (IIb) | 69168 | C6H3ClN3.POM | 详情 | 详情 | ||
| (Va) | 68072 | 4-(1H-pyrazol-4-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine | C15H21N5OSi | 详情 | 详情 | |
| (Vb) | 69169 | C9H6N5.POM | 详情 | 详情 | ||
| (IXa) | 69172 | (R)-3-cyclopentyl-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)propanenitrile | C23H32N6OSi | 详情 | 详情 | |
| (IXb) | 69175 | C17H17N6.POM | 详情 | 详情 | ||
| (XIa) | 69173 | (R)-3-cyclopentyl-3-(4-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl)propanal | C23H33N5O2Si | 详情 | 详情 | |
| (XIb) | 69174 | C17H18N5O.POM | 详情 | 详情 | ||
| (I) | 60046 | 4-chloro-7H-pyrrolo[2,3-d]pyrimidine；6-Chloro-7-deazapurine；4-chloropyrrolo[2,3-d]pyrimidine；4-Chloro-1H-pyrrolo[2,3-d]pyrimidine | 3680-69-1 | C6H4ClN3 | 详情 | 详情 |
| (III) | 68071 | 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | C13H23BN2O3 | 详情 | 详情 | |
| (IV) | 68081 | 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | C9H15BN2O2 | 详情 | 详情 | |
| (VI) | 69170 | cyclopentylcarboxaldehyde;3-cyclopentyl-2-Propenenitrile | 591769-05-0 | C8H11N | 详情 | 详情 |
| (VII) | 69171 | cyclopentylcarboxaldehyde；Cyclopentanecarbaldehyde;Cyclopentanealdehyde;Cyclopentyl aldehyde;Cyclopentylformaldehyde;Formylcyclopentane | 872-53-7 | C6H10O | 详情 | 详情 |
| (VIII) | 10045 | Diethyl cyanomethylphosphonate | 2537-48-6 | C6H12NO3P | 详情 | 详情 |
| (X) | 69176 | (E)-3-cyclopentylacrylaldehyde | C8H12O | 详情 | 详情 | |
| (XII) | 69177 | (S)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile | C17H26BN3O2 | 详情 | 详情 |