3-(Furan-2-yl)-2-oxopropanoic acid → 8-benzyl-2-(furan-2-ylmethyl)-6-phenyl-7H-imidazo[1,2-a]pyrazin-3-one

HRID 2407202Notes

Reaction equation

HRID 2407202 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7](=O)[C:8]([OH:10])=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:8](=[O:10])[C:7]([CH2:6][C:2]3[O:1][CH:5]=[CH:4][CH:3]=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 20497783-(Furan-2-yl)-2-oxopropanoic acidHCID 102146592-Amino-3-benzyl-5-phenylpyrazine

Product 1

HCID 1785156418-benzyl-2-(furan-2-ylmethyl)-6-phenyl-7H-imidazo[1,2-a]pyrazin-3-one

Procedure

Synthesized from method C using 3-(furan-2-yl)-2-oxopropanoic acid and 3-benzyl-5-phenylpyrazin-2-amine as starting materials. 1H NMR (300 MHz, dmso) δ 8.88 (s, 1H), 8.02 (d, J=7.9, 2H), 7.61-7.38 (m, 6H), 7.37-7.14 (m, 3H), 6.38 (s, 1H), 6.26 (d, J=3.2, 1H), 4.64 (s, 3H), 4.40 (s, 3H); exact mass calculated for C24H20N3O2+ m/z+ 382.16, found m/z+ 382.

Workup

  1. customSynthesized from method C

Sources & evidence

ORD record
ord-a5b957733a0546b0a9635c81050e6c24
Source dataset
uspto-grants-2014_08
Patent number
US08809529B2

Reaction notes

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