Acryloyl chloride → HCID 86720315, compound

HRID 928330Notes

Reaction equation

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

Participants

Reactant 2

HCID 13140Acryloyl chloride

HCID 71226446HCID 71226446, compound2×

Product 1

HCID 86720315HCID 86720315, compoundYield 26.2%

Procedure

This compound was prepared, in an analogous manner as described in Example 1, from (S)-4-(8-amino-3-(piperidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyrimidin-2-yl)benzamide (intermediate 27) and acryloylchloride, to afford the title compound (5.9 mg, 26.2%). Data: UPLC(C) Rt: 1.70 min; m/z 469.3 (M+H)+.

Workup

customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record: ord-bcf2883b59e84b06b7f23bfedb1f85d7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290504B2

Reaction notes

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