4-Hydroxy-4-methylpent-2-ynoic acid → (S)-4-(8-Amino-3-(1-(4-hydroxy-4-methylpent-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide

HRID 928343Notes

Reaction equation

HRID 928343 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:26]3[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[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:16])=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[OH:31][C:32]([CH3:39])([CH3:38])[C:33]#[C:34][C:35](O)=[O:36]>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:26]3[CH2:30][CH2:29][CH2:28][N:27]3[C:35](=[O:36])[C:34]#[C:33][C:32]([OH:31])([CH3:39])[CH3:38])=[N:9][C:10]=2[C:11]2[CH:25]=[CH:24][C:14]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)=[O:16])=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 31641664-Hydroxy-4-methylpent-2-ynoic acidHCID 71226368(S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide

Product 1

HCID 71226505(S)-4-(8-Amino-3-(1-(4-hydroxy-4-methylpent-2-ynoyl)pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamideYield 25.1%

Procedure

This compound was prepared, in an analogous manner as described in Example 2, from the compound described in intermediate 2b and 4-hydroxy-4-methylpent-2-ynoic acid, to afford the title compound (8.0 mg, 25.1%). Data: UPLC (C) Rt: 1.53 min; m/z 510.3 (M+H)+.

Workup

  1. customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record
ord-5662687f6f1540efa2ffb8eefea9a725
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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