3-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-(3-trifluoromethyl-phenyl)-benzamide → N-(2-Bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

Participants

Role	Name	HCID	Charge
Reactant	3-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-(3-trifluoromethyl-phenyl)-benzamide	HCID 24757614	—
Reactant	N'-(3-Cyano-pyridin-2-yl)-N,N-dimethyl-formamidine	HCID 66808319	—
Reactant	3-Amino-N-(4-bromo-phenyl)-4-(4-hydroxy-phenylsulfanyl)-benzamide	HCID 67040269	—
Reactant	3-Amino-N-(2-bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-benzamide	HCID 67040346	—
Product	N-(2-Bromo-benzyl)-4-(4-hydroxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide	HCID 67040661	60%

Reaction Steps

The product of Example 31A was reacted with the product of Example 29A using the procedure of Example 22C substituting the product of Example 3 1A for the product of Example 22B and substituting the product of Example 29A for the product of Example 8E to provide the crude title compound which was purified by column chromatography on silica gel using methanol/dichloromethane as eluent to provide the title product (58 mg, 60%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 4.48 (d, J=5.88 Hz, 2 H) 6.84 (d, J=8.46 Hz, 2 H) 6.87-7.02 (m, 1 H) 7.13-7.44 (m, 5 H) 7.58-7.64 (m, 1 H) 7.64-7.84 (m, 2 H) 7.93 (s, 1 H) 8.62 (d, J=1.84 Hz, 1 H) 8.82-9.20 (m, 3 H) 9.94 (s, 1 H) 10.30 (s, 1 H); MS (ESI+) m/z 558/560 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07910595B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-2364f559f6824ae08fb5158aeda9a812
Source note	uspto-grants-2011_03