Acryloyl chloride → HCID 86720314, compound

HRID 928328Notes

Reaction equation

[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:28]3[CH2:33][CH2:32][CH2:31][CH2:30][NH:29]3)=[N:9][C:10]=2[C:11]2[CH:27]=[CH:26][C:14]([C:15]([NH:17][C:18]3[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][N:19]=3)=[O:16])=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[C:34](Cl)(=[O:37])[CH:35]=[CH2:36]>>[C:34]([N:29]1[CH2:30][CH2:31][CH2:32][CH2:33][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:12]=[CH:13][C:14]([C:15]([NH:17][C:18]3[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][N:19]=3)=[O:16])=[CH:26][CH:27]=2)[N:9]=1)(=[O:37])[CH:35]=[CH2:36]

Participants

Reactant 2

HCID 13140Acryloyl chloride

HCID 71226716HCID 71226716, compound2×

Product 1

HCID 86720314HCID 86720314, compoundYield 10.4%

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-cyanopyridin-2-yl)benzamide (intermediate 24) and acryloylchloride, to afford the title compound (4.8 mg, 10.4%). Data: UPLC(C) Rt: 2.31 min.

Workup

customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record: ord-82ab9407fd944e5d88784420a725eb82
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290504B2

Reaction notes

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