(2E)-4-(Dimethylamino)-2-butenoic acid → (S,E)-4-(8-Amino-3-(1-(4-(dimethylamino)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(thiazol-2-yl)benzamide

HRID 928325Notes

Reaction equation

HRID 928325 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:25]3[CH2:29][CH2:28][CH2:27][NH:26]3)=[N:9][C:10]=2[C:11]2[CH:24]=[CH:23][C:14]([C:15]([NH:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)=[O:16])=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH3:30][N:31]([CH3:38])[CH2:32]/[CH:33]=[CH:34]/[C:35](O)=[O:36]>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:25]3[CH2:29][CH2:28][CH2:27][N:26]3[C:35](=[O:36])/[CH:34]=[CH:33]/[CH2:32][N:31]([CH3:38])[CH3:30])=[N:9][C:10]=2[C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)=[O:16])=[CH:23][CH:24]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 14805664(2E)-4-(Dimethylamino)-2-butenoic acidHCID 86720312(S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(thiazol-2-yl)benzamide2×

Product 1

HCID 71607622(S,E)-4-(8-Amino-3-(1-(4-(dimethylamino)but-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(thiazol-2-yl)benzamideYield 29.7%

Procedure

This compound was prepared, in an analogous manner as described in Example 2, from (S)-4-(8-amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(thiazol-2-yl)benzamide (intermediate 20) and (E)-4-(dimethylamino)but-2-enoic acid, to afford the title compound (18.9 mg, 29.7%). Data: UPLC (C) Rt: 1.38 min; m/z 517.3 (M+H)+.

Workup

  1. customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record
ord-fda8f99c586c48238d256b83abfbe119
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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