5-Amino-2-fluorobenzamide → 2-(3-Carbamoyl-4-fluorophenylamino)-2-(4-fluoro-3-methoxyphenyl)acetic acid

HRID 1515526Notes

Reaction equation

HRID 1515526 reaction equation
C(C1C=C(N[CH:11]([C:15]2[CH:20]=[CH:19][C:18](OC)=[C:17]([O:23][CH3:24])[CH:16]=2)[C:12]([OH:14])=[O:13])C=CC=1)(=O)N.[NH2:25][C:26]1[CH:27]=[C:28]([C:32]([F:35])=[CH:33][CH:34]=1)[C:29]([NH2:31])=[O:30].COC1C=C(B(O)O)C=CC=1[F:44].O.C(O)(=O)C=O>>[C:29]([C:28]1[CH:27]=[C:26]([NH:25][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([F:44])=[C:17]([O:23][CH3:24])[CH:16]=2)[C:12]([OH:14])=[O:13])[CH:34]=[CH:33][C:32]=1[F:35])(=[O:30])[NH2:31]

Participants

5

Reactant 4

HCID 27788995-Amino-2-fluorobenzamideHCID 15620607Glyoxylic acid, monohydrateHCID 44558185(4-Fluoro-3-methoxyphenyl)boronic acidHCID 598380342-(3-Carbamoylphenylamino)-2-(3,4-dimethoxyphenyl)acetic acid

Product 1

HCID 594794522-(3-Carbamoyl-4-fluorophenylamino)-2-(4-fluoro-3-methoxyphenyl)acetic acidYield 43%

Procedure

39A was prepared in a procedure similar to that of 1A using 3-amino-6-fluorobenzamide, 7C and glyoxylic acid monohydrate. Yield: 43%. 1H NMR (400 MHz, Methanol-d4) δ ppm 3.85 (s, 3H) 5.05 (s, 1H) 6.75-6.82 (m, 1H) 6.92-6.97 (m, 1H) 7.03-7.08 (m, 3H) 7.24-7.29 (m, 1H), LCMS: 337 (M+1).

Sources & evidence

ORD record
ord-bf8887147a0847b093cac9578fb8264e
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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