N-(4-ethylpyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide → (S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-ethylpyridin-2-yl)benzamide

HRID 928315Notes

Reaction equation

HRID 928315 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.[CH2:27]([C:29]1[CH:34]=[CH:33][N:32]=[C:31]([NH:35][C:36](=[O:52])[C:37]2[CH:42]=[CH:41][C:40](B3OC(C)(C)C(C)(C)O3)=[CH:39][CH:38]=2)[CH:30]=1)[CH3:28]>>[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:40]2[CH:41]=[CH:42][C:37]([C:36]([NH:35][C:31]3[CH:30]=[C:29]([CH2:27][CH3:28])[CH:34]=[CH:33][N:32]=3)=[O:52])=[CH:38][CH:39]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 71222661N-(4-ethylpyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide2×HCID 71233875(S)-Benzyl 2-(8-amino-1-bromoimidazo(1,5-a)pyrazin-3-yl)pyrrolidine-1-carboxylate2×

Product 1

HCID 71225845(S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-ethylpyridin-2-yl)benzamideYield 89%

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 N-(4-ethylpyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (intermediate 12) to afford the title compound (133.8 mg, 89%).

Workup

  1. customThis intermediate was prepared, in an analogous manner

Sources & evidence

ORD record
ord-9d53db01700b4c17b00789619fd28701
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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