1-(4-Amino-3-fluorophenyl)pyrazin-2(1H)-one → 3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid [2-fluoro-4-(2-oxo-2H-pyrazine-1-yl)-phenyl]-amide

HRID 2237643Notes

Reaction equation

HRID 2237643 reaction equation
C(O[C:4]([C:6]1[O:10][N:9]=[C:8]([CH2:11][NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[N:7]=1)=[O:5])C.[NH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:33]=[CH:32][N:31]=[CH:30][C:29]2=[O:34])=[CH:24][C:23]=1[F:35]>>[F:35][C:23]1[CH:24]=[C:25]([N:28]2[CH:33]=[CH:32][N:31]=[CH:30][C:29]2=[O:34])[CH:26]=[CH:27][C:22]=1[NH:21][C:4]([C:6]1[O:10][N:9]=[C:8]([CH2:11][NH:12][C:13]([C:15]2[S:16][C:17]([Cl:20])=[CH:18][CH:19]=2)=[O:14])[N:7]=1)=[O:5]

Participants

3

Reactant 2

HCID 230867741-(4-Amino-3-fluorophenyl)pyrazin-2(1H)-oneHCID 593029563-{[(5-Chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester

Product 1

HCID 249676303-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid [2-fluoro-4-(2-oxo-2H-pyrazine-1-yl)-phenyl]-amide

Procedure

In analogy to example 1E 3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5carboxylic acid ethyl ester (example 1D) was reacted with 1-(4-amino-3-fluoro-phenyl)-pyrazine-2-one (CAS 863015-77-4) to give 3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-[1,2,4]oxadiazole-5-carboxylic acid [2-fluoro-4-(2-oxo-2H-pyrazine-1-yl)-phenyl]-amide. Yellow solid. MS 475.0 ([M+H]−)

Sources & evidence

ORD record
ord-4b7f658ec16048299aca9d0f0231a21b
Source dataset
uspto-grants-2010_05
Patent number
US07718679B2

Reaction notes

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