HCID 71222557, compound → HCID 71226346, compound

HRID 928320Notes

Reaction equation

HRID 928320 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.[F:27][C:28]1[CH:42]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:40]=[CH:39][C:29]=1[C:30]([NH:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)=[O:31]>>[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:40]=[CH:39][C:29]([C:30]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[O:31])=[C:28]([F:27])[CH:42]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 71222557HCID 71222557, compound2×HCID 71233875(S)-Benzyl 2-(8-amino-1-bromoimidazo(1,5-a)pyrazin-3-yl)pyrrolidine-1-carboxylate2×

Product 1

HCID 71226346HCID 71226346, compoundYield 76%

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 2-Fluoro-N-(pyridin-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (intermediate 16) to afford the title compound (160 mg, 76%).

Workup

  1. customThis intermediate was prepared, in an analogous manner

Sources & evidence

ORD record
ord-546e0c79a2ea4a5ba980ca03bb93255f
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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