1-(4-Amino-3-fluorophenyl)pyridin-2-one → 4-chloro-N-(2-(2-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenylamino)-2-oxoethyl)-2H-tetrazol-5-yl)cyclopenta-1,3-dienecarboxamide

HRID 2237573Notes

Reaction equation

HRID 2237573 reaction equation
CO[C:3](=[O:19])[CH2:4][N:5]1[N:9]=[N:8][C:7]([NH:10][C:11]([C:13]2[S:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[O:12])=[N:6]1.[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]2=[O:33])=[CH:23][C:22]=1[F:34]>>[F:34][C:22]1[CH:23]=[C:24]([N:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]2=[O:33])[CH:25]=[CH:26][C:21]=1[NH:20][C:3]([CH2:4][N:5]1[N:9]=[N:8][C:7]([NH:10][C:11]([C:13]2[S:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[O:12])=[N:6]1)=[O:19]

Participants

3

Reactant 2

HCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-oneHCID 42643127{5-[(5-Chloro-thiophene-2-carbonyl)-amino]-tetrazol-2-yl}-acetic acid methyl ester

Product 1

HCID 426431774-chloro-N-(2-(2-(2-fluoro-4-(2-oxopyridin-1(2H)-yl)phenylamino)-2-oxoethyl)-2H-tetrazol-5-yl)cyclopenta-1,3-dienecarboxamide

Procedure

63.3 Using general method F, {5-[(5-chloro-thiophene-2-carbonyl)-amino]-tetrazol-2-yl}-acetic acid methyl ester was reacted with 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (CAS 536747-52-1, prepared according to C. F. Bigge et al., patent application WO 2003045912) to give 5-chloro-thiophene-2-carboxylic acid (2-{[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-methyl}-2H-tetrazol-5-yl)-amide. Off-white solid. MS 474.3 ([M+H]+)

Sources & evidence

ORD record
ord-827b2e6967314757889e433a4270ba48
Source dataset
uspto-grants-2010_05
Patent number
US07718659B2

Reaction notes

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