Potassium Carbonate → tert-butyl (1S,2R)-2-(5-cyano-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)cyclohexylcarbamate
반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:5]=[N:4][C:3]=1[C:23]#[N:24].[N:25]1[CH:30]=[CH:29][CH:28]=[N:27][C:26]=1[C:31]1[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=1)[NH2:34].C([O-])([O-])=O.[K+].[K+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:23]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[N:7][C:2]=1[NH:34][C:33]1[CH:35]=[CH:36][CH:37]=[C:31]([C:26]2[N:25]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH:32]=1)#[N:24]참가 물질
7
반응물 4
생성물 1
시약·촉매·용매 2
실험 절차
A mixture of tert-butyl (1S,2R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)cyclohexylcarbamate (100 mg, 0.284 mmol), 3-(pyrimidin-2-yl)aniline (100 mg, 0.584 mmol), K2CO3 (118 mg, 0.855 mmol), BINAP (30 mg, 0.048 mmol) and Pd(OAc)2 (15 mg, 0.066 mmol) in dioxane (2 mL) was degassed with Ar, then was stirred at 110 C for 20 h. Water and EtOAc were added. Organic phase was separated, dried over Na2SO4, concentrated in vacuo to give a crude tert-butyl (1S,2R)-2-(5-cyano-6-(3-(pyrimidin-2-yl)phenylamino)pyrazin-2-ylamino)cyclohexylcarbamate.
후처리
- customwas degassed with Ar
- additionWater and EtOAc were added
- customOrganic phase was separated
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
출처 및 근거
- ORD 기록
- ord-5f0ffb7d5f99427db3975554dcaf8fee
- 출처 데이터셋
- uspto-grants-2016_06
- 특허 번호
- US09359308B2
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