5-Amino-2-fluorobenzamide → 2-(3-Carbamoyl-4-fluorophenylamino)-2-(3-ethoxy-4-isopropoxyphenyl)acetic acid

Participants

Role	Name	HCID	Charge
Reactant	5-Amino-2-fluorobenzamide	HCID 2778899	—
Reactant	Glyoxylic acid, monohydrate	HCID 15620607	—
Reactant	2-(3-Carbamoyl-4-fluorophenylamino)-2-(3,4-dimethoxyphenyl)acetic acid	HCID 59479392	—
Reactant	Boronic acid, [3-ethoxy-4-(1-methylethoxy)phenyl]-	HCID 59838044	—
Product	2-(3-Carbamoyl-4-fluorophenylamino)-2-(3-ethoxy-4-isopropoxyphenyl)acetic acid	HCID 59479509	55%

Reaction Steps

21A was prepared in a procedure similar to that of 13A using 3-amino-6-fluorobenzamide, 3-ethoxy-4-isopropoxyphenylboronic acid and glyoxylic acid monohydrate. Yield: 55%. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.28 (s, 3H) 1.29 (s, 3H) 1.37 (t, J=7.03 Hz, 3H) 4.05 (q, J=7.03 Hz, 2H) 4.46-4.55 (m, 1H) 5.00 (s, 1H) 6.78-6.84 (m, 1H) 6.90-6.99 (m, 2H) 7.02 (dd, J=8.35, 2.20 Hz, 1H) 7.07-7.12 (m, 2H), LCMS: 391 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08222453B2
Source dataset	uspto-grants-2012_07
ORD ID	ord-bb9b923e0772422ba7f5f7438d6273da
Source note	uspto-grants-2012_07