B-(4-((2-Thiazolylamino)carbonyl)phenyl)boronic acid → (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(thiazol-2-yl)benzamide

HRID 928324Notes

Reaction equation

HRID 928324 reaction equation
[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[CH:31]=[CH:30][N:29]=[C:28]1[NH:32][C:33](=[O:43])[C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=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:37]2[CH:38]=[CH:39][C:34]([C:33]([NH:32][C:28]3[S:27][CH:31]=[CH:30][N:29]=3)=[O:43])=[CH:35][CH:36]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 44118748B-(4-((2-Thiazolylamino)carbonyl)phenyl)boronic acidHCID 71233875(S)-Benzyl 2-(8-amino-1-bromoimidazo(1,5-a)pyrazin-3-yl)pyrrolidine-1-carboxylate2×

Product 1

HCID 86720312(S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(thiazol-2-yl)benzamideYield 73.1%

Procedure

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 commercially available N-2-thiazolyl 4-boronobenzamide to afford the title compound (229 mg, 73.1%).

Workup

  1. customThis intermediate was prepared, in an analogous manner

Sources & evidence

ORD record
ord-f29d5c75414e470ebe02568b1087aa5d
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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