2-OXO-3-(2-THIENYL)PROPANOIC ACID → 8-benzyl-6-phenyl-2-(thiophen-2-ylmethyl)-7H-imidazo[1,2-a]pyrazin-3-one

HRID 1184327Notes

Reaction equation

HRID 1184327 reaction equation
O=[C:2]([CH2:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[C:3]([OH:5])=O.[CH2:12]([C:19]1[C:20]([NH2:31])=[N:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:12]([C:19]1[NH:24][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:22][N:21]2[C:3](=[O:5])[C:2]([CH2:6][C:7]3[S:8][CH:9]=[CH:10][CH:11]=3)=[N:31][C:20]=12)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 20497802-OXO-3-(2-THIENYL)PROPANOIC ACIDHCID 102146592-Amino-3-benzyl-5-phenylpyrazine

Product 1

HCID 1785156628-benzyl-6-phenyl-2-(thiophen-2-ylmethyl)-7H-imidazo[1,2-a]pyrazin-3-one

Procedure

Synthesized from method C using 2-oxo-3-(thiophen-2-yl)propanoic acid and 3-benzyl-5-phenylpyrazin-2-amine as starting materials. 1H NMR (300 MHz, dmso) δ 8.85 (s, 1H), 7.99 (d, J=6.8, 2H), 7.63-7.02 (m, 10H), 6.94 (dd, J=3.5, 5.1, 1H), 4.62 (s, 2H), 4.58 (s, 2H), 2.69 (contaminate); exact mass calculated for C24H20N3OS+ m/z+398.13, found m/z+398.

Workup

  1. customSynthesized from method C

Sources & evidence

ORD record
ord-6dcab653e3694cadac03acaef7e96d96
Source dataset
uspto-grants-2014_03
Patent number
US08669103B2

Reaction notes

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