Acryloyl chloride → HCID 86720311, compound

HRID 928323Notes

Reaction equation

HRID 928323 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:28]3[CH2:32][CH2:31][CH2:30][NH:29]3)=[N:9][C:10]=2[C:11]2[CH:25]=[CH:24][C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:16])=[C:13]([O:26][CH3:27])[CH:12]=2)[CH:5]=[CH:6][N:7]=1.[C:33](Cl)(=[O:36])[CH:34]=[CH2:35]>>[C:33]([N:29]1[CH2:30][CH2:31][CH2:32][C@H:28]1[C:8]1[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]2=[C:10]([C:11]2[CH:25]=[CH:24][C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:16])=[C:13]([O:26][CH3:27])[CH:12]=2)[N:9]=1)(=[O:36])[CH:34]=[CH2:35]

Participants

3

Reactant 2

HCID 13140Acryloyl chlorideHCID 71226538HCID 71226538, compound2×

Product 1

HCID 86720311HCID 86720311, compoundYield 35.5%

Procedure

This compound was prepared, in an analogous manner as described in Example 1, from (S)-4-(8-amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-2-methoxy-N-(pyridin-2-yl)benzamide (intermediate 19) and acryloylchloride, to afford the title compound (14 mg, 35.5%). Data: UPLC (C) Rt: 1.74 min; m/z 484.3 (M+H)+.

Workup

  1. customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record
ord-5aff5434d7ac420ca884cac90b8f1716
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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