(2E)-4-methoxybut-2-enoic acid → (S,E)-4-(8-Amino-3-(1-(4-methoxybut-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-propylpyridin-2-yl)benzamide

HRID 928311Notes

Reaction equation

HRID 928311 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:29]3[CH2:33][CH2:32][CH2:31][NH:30]3)=[N:9][C:10]=2[C:11]2[CH:28]=[CH:27][C:14]([C:15]([NH:17][C:18]3[CH:23]=[C:22]([CH2:24][CH2:25][CH3:26])[CH:21]=[CH:20][N:19]=3)=[O:16])=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH3:34][O:35][CH2:36]/[CH:37]=[CH:38]/[C:39](O)=[O:40]>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:29]3[CH2:33][CH2:32][CH2:31][N:30]3[C:39](=[O:40])/[CH:38]=[CH:37]/[CH2:36][O:35][CH3:34])=[N:9][C:10]=2[C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:17][C:18]3[CH:23]=[C:22]([CH2:24][CH2:25][CH3:26])[CH:21]=[CH:20][N:19]=3)=[O:16])=[CH:27][CH:28]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 15302979(2E)-4-methoxybut-2-enoic acid2×HCID 71226711(S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-propylpyridin-2-yl)benzamide2×

Product 1

HCID 71226728(S,E)-4-(8-Amino-3-(1-(4-methoxybut-2-enoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-propylpyridin-2-yl)benzamideYield 65.7%

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-(4-propylpyridin-2-yl)benzamide (intermediate 9) and (E)-4-methoxybut-2-enoic acid (Intermediate 3), to afford the title compound (30.9 mg, 65.7%). Data: UPLC (C) R: 2.73 min; m/z 566.3 (M+H)+.

Workup

  1. customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record
ord-4cbb38d902264e20b236d9b192b8f9ae
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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