Acryloyl chloride → HCID 86720316, compound

HRID 928331Notes

Reaction equation

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

Participants

Reactant 2

HCID 13140Acryloyl chloride

HCID 71226005HCID 71226005, compound2×

Product 1

HCID 86720316HCID 86720316, compoundYield 27.4%

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-(4-methylpyrimidin-2-yl)benzamide (intermediate 29) and acryloylchloride, to afford the title compound (4.5 mg, 27.4%). Data: UPLC(C) Rt: 1.79 min; m/z 483.3 (M+H)+.

Workup

customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record: ord-c8433629019c4073a6c1a52d4ea9401f
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290504B2

Reaction notes

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