N-(2-aminophenyl)-4-((4-(4-(2-(dimethylamino)ethoxy)phenyl)pyrimidin-2-ylamino)methyl)benzamide → N-(2-Amino-phenyl)-4-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-benzamide

Participants

Role	Name	HCID	Charge
Reactant	N-(2-aminophenyl)-4-((4-(4-(2-(dimethylamino)ethoxy)phenyl)pyrimidin-2-ylamino)methyl)benzamide	HCID 44570974	—
Reactant	2-(4-Trifluoromethoxy-phenyl)-benzothiazole-6-carboxylic acid (2-aminophenyl)-amide	HCID 66622185	—
Reactant	{2-[4-(2,4-Dioxo-thiazolidin-5-ylidenemethyl)-benzoylamino]-phenyl}-carbamic acid tert-butyl ester	HCID 72466473	—
Product	N-(2-Amino-phenyl)-4-(2,4-dioxo-thiazolidin-5-ylidenemethyl)-benzamide	HCID 72466478	37%

Reaction Steps

Following the procedure described for the synthesis of compound 117 (scheme 28) but substituting the amide 116 by the amide 348, title compound was obtained in 37% yield. 1H NMR: (400 MHz, DMSO-d6, δ (Ppm): 9.72 (s, 1H), 8.06 (d, j=8.2 Hz, 2H), 7.79 (s, 1H), 7.69 (d, J=8.4, 2H), 7.14 (d (dd) J=7.8, 1H), 6.95 (d (dd), J=1.6 Hz, J=9.0, 1H), 6.75 (dd, J=1.2 Hz, J=8.0 Hz, 1H), 6.56 (t (dd), J=7.2 Hz 1H). LRMS: 339.4 (calcd.), 340.4 [MH]+ (found).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08088805B2
Source dataset	uspto-grants-2012_01
ORD ID	ord-61aacd5e8ad9468aa879aae3a33f2b1d
Source note	uspto-grants-2012_01