2-Methyl-3-oxo-3-(phenylamino)propanoic acid → N1-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-methyl-N3-phenylmalonamide

Participants

Role	Name	HCID	Charge
Reactant	2-Methyl-3-oxo-3-(phenylamino)propanoic acid	HCID 12605880	—
Reactant	N-(2-Methoxy-phenyl)-malonamic acid	HCID 12664594	—
Reactant	N1-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-N3-(2-methoxyphenyl)malonamide	HCID 16040869	—
Reactant	3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine	HCID 59424480	—
Product	N1-(3-Fluoro-4-(2-(1-methyl-1H-imidazol-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)-2-methyl-N3-phenylmalonamide	HCID 16041061	—

Reaction Steps

Starting from the amine 9 and following the procedure described above for compound 28a (example 8, step 2) but substituting acid 27 for the acid 37, title compound 38 was obtained as a white solid (20% yield). 1H NMR (d6-DMSO) δ (ppm): 10.99 (s, 1H), 10.51 (s, 1H), 8.64 (d. 1H), 8.25 (s, 1H), 7.94 (s, 1H), 7.80 (s, 1H), 7.65 (d, 2H) 7.57-7.48 (m, 2H), 7.28 (t, 2H), 7.03 (t, 1H), 6.88 (d, 1H), 4.08 (s, 3H), 1.18 (s, 3H). MS (m/z): 516.1 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08093264B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-a22b275402b343048a1d6ed0faa830c7
Source note	uspto-grants-2012_01