(S)-Benzyl 2-(8-amino-1-bromoimidazo(1,5-a)pyrazin-3-yl)pyrrolidine-1-carboxylate → (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)benzamide

HRID 928318노트

반응식

HRID 928318 반응식
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:12]3[CH2:16][CH2:15][CH2:14][N:13]3C(OCC3C=CC=CC=3)=O)=[N:9][C:10]=2Br)[CH:5]=[CH:6][N:7]=1.[S:27]1[C:31]2[CH2:32][CH2:33][CH2:34][CH2:35][C:30]=2[N:29]=[C:28]1[NH:36][C:37](=[O:53])[C:38]1[CH:43]=[CH:42][C:41](B2OC(C)(C)C(C)(C)O2)=[CH:40][CH:39]=1>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:12]3[CH2:16][CH2:15][CH2:14][NH:13]3)=[N:9][C:10]=2[C:41]2[CH:42]=[CH:43][C:38]([C:37]([NH:36][C:28]3[S:27][C:31]4[CH2:32][CH2:33][CH2:34][CH2:35][C:30]=4[N:29]=3)=[O:53])=[CH:39][CH:40]=2)[CH:5]=[CH:6][N:7]=1

참가 물질

3

반응물 2

HCID 71233875(S)-Benzyl 2-(8-amino-1-bromoimidazo(1,5-a)pyrazin-3-yl)pyrrolidine-1-carboxylate2회HCID 86720308N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2회

생성물 1

HCID 71607621(S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)benzamide수율 60%

실험 절차

This intermediate was prepared, in an analogous manner as described for intermediate 2, from (S)-benzyl 2-(8-amino-1-bromoimidazo[1,5-a]pyrazin-3-yl)pyrrolidine-1-carboxylate (Intermediate 1e) and N-(4,5,6,7-tetrahydrobenzo[d]thiazol-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (intermediate 14b) to afford the title compound (260 mg, 60%).

후처리

  1. customThis intermediate was prepared, in an analogous manner

출처 및 근거

ORD 기록
ord-4573eeca54f1419f80840ebe10c26b9d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290504B2

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