2-Butynoic acid → HCID 86720321, compound

HRID 928341Notes

Reaction equation

HRID 928341 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:26]([NH2:28])[CH3:27])=[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.[C:29](O)(=[O:33])[C:30]#[C:31][CH3:32]>>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([C@@H:26]([NH:28][C:29](=[O:33])[C:30]#[C:31][CH3:32])[CH3:27])=[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 685352-Butynoic acidHCID 71226593HCID 71226593, compound2×

Product 1

HCID 86720321HCID 86720321, compoundYield 26.9%

Procedure

This compound was prepared, in an analogous manner as described in Example 2, from (S)-4-(8-amino-3-(1-aminoethyl)imidazo[1,5-a]pyrazin-1-yl)-N-(pyridin-2-yl)benzamide (intermediate 45) and 2-butynoic acid, to afford the title compound (9.5 mg, 26.9%). Data: UPLC(C) Rt: 1.38 min; m/z 440.3 (M+H)+.

Workup

  1. customThis compound was prepared, in an analogous manner

Sources & evidence

ORD record
ord-ab22608c25ef44afab89244f2ed34370
Source dataset
uspto-grants-2016_03
Patent number
US09290504B2

Reaction notes

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