2-Butynoic acid → US9758524, Example 10

HRID 928314Notes

Reaction equation

HRID 928314 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:30]3[CH2:34][CH2:33][CH2:32][NH:31]3)=[N:9][C:10]=2[C:11]2[CH:29]=[CH:28][C:14]([C:15]([NH:17][C:18]3[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=3)=[O:16])=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[C:35](O)(=[O:39])[C:36]#[C:37][CH3:38]>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:30]3[CH2:34][CH2:33][CH2:32][N:31]3[C:35](=[O:39])[C:36]#[C:37][CH3:38])=[N:9][C:10]=2[C:11]2[CH:29]=[CH:28][C:14]([C:15]([NH:17][C:18]3[CH:23]=[C:22]([C:24]([F:25])([F:27])[F:26])[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 685352-Butynoic acidHCID 86720306(S)-4-(8-Amino-3-(pyrrolidin-2-yl)imidazo[1,5-a]pyrazin-1-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide2×

Product 1

HCID 71226328US9758524, Example 10Yield 31.1%

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-(trifluoromethyl)pyridin-2-yl)benzamide (intermediate 11) and 2-butynoic acid, to afford the title compound (7.1 mg, 31.1%). Data: UPLC (C) Rt: 2.63 min; m/z 534.2 (M+H)+.

Workup

  1. customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record
ord-fccc351f7ff54765877adc735f20a9a6
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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