m-Toluidine → 3-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-m-tolyl-benzamide

Participants

Role	Name	HCID	Charge
Reactant	m-Toluidine	HCID 7934	—
Reactant	5-Amino-2-methylphenol	HCID 17818	—
Reactant	3-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzoyl chloride	HCID 86615550	—
Product	3-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-N-m-tolyl-benzamide	HCID 67040349	—

Reaction Steps

The product from Example 137B was reacted with m-toluidine according to the procedure from Example 137C substituting m-toluidine for 5-amino-o-cresol to provide the title compound as an off white solid after silica gel chromatography (56 mg, 70%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.34 (d, J=6.99 Hz, 6H), 2.21 (s, 3H), 3.15-3.29 (m, 1H), 3.78 (s, 3H), 7.00 (d, J=8.82 Hz, 2H), 7.12-7.37 (m, 4H), 7.40 (d, J=8.82 Hz, 2H), 7.64 (d, J=8.46 Hz, 1H), 7.84 (d, J=11.40 Hz, 1H), 7.99 (s, 1H), 8.59 (s, 1H), 8.86 (d, J=8.46 Hz, 1H), 9.87 (s, 1H), 10.21 (s, 1H); MS (APCI) m/z 536 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07910595B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-654d6b4f6fa04d55a1b06bc5218e5d23
Source note	uspto-grants-2011_03