5-Amino-2-methylphenol → N-(4-Cyanomethyl-phenyl)-4-(4-methoxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

HRID 605285Notes

Reaction equation

HRID 605285 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][C:10]2[CH:18]=[CH:17][C:13]([C:14](Cl)=[O:15])=[CH:12][C:11]=2[NH:19][C:20]2[C:21]3[CH:29]=[CH:28][CH:27]=[N:26][C:22]=3[N:23]=[CH:24][N:25]=2)=[CH:5][CH:4]=1.[NH2:30][C:31]1[CH:39]=[CH:38][C:34]([CH2:35][C:36]#[N:37])=[CH:33][CH:32]=1.NC1C=C(O)C(C)=CC=1.C(C1C=CC2C(NC3C=C(C=CC=3SC3C=CC(OC)=CC=3)C(Cl)=O)=NC=NC=2N=1)(C)C>CO>[C:36]([CH2:35][C:34]1[CH:38]=[CH:39][C:31]([NH:30][C:14](=[O:15])[C:13]2[CH:17]=[CH:18][C:10]([S:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)=[C:11]([NH:19][C:20]3[C:21]4[CH:29]=[CH:28][CH:27]=[N:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH:12]=2)=[CH:32][CH:33]=1)#[N:37]

Participants

6

Reactant 4

HCID 178185-Amino-2-methylphenolHCID 770004-AminophenylacetonitrileHCID 866155503-(7-Isopropyl-pyrido[2,3-d]pyrimidin-4-ylamino)-4-(4-methoxy-phenylsulfanyl)-benzoyl chlorideHCID 866155614-(4-Methoxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzoyl chloride2×

Product 1

HCID 67041030N-(4-Cyanomethyl-phenyl)-4-(4-methoxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 260B was reacted with 4-aminobenzyl cyanide according to the procedure from Example 137C substituting 4-aminobenzyl cyanide for 5-amino-o-cresol and substituting the product from Example 260B for the product from Example 137B to provide the title compound as an off white solid after trituration of the reaction product from methanol (54.7 mg, 64%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 10.60 (s, 1 H), 10.26 (s, 1 H), 9.09 (s, 1 H), 8.95 (s, 1 H), 8.65 (s, 1 H), 7.98 (s, 1 H), 7.64-7.89 (m, J=8.46 Hz, 4 H), 7.36-7.47 (m, 2 H), 7.31 (d, J=8.82 Hz, 2 H), 6.91-7.07 (m, 3 H), 3.99 (s, 2 H), 3.78 (s, 3 H); MS (ESI+) m/z 519.4 (M+H)+, (ESI−) m/z 517.1 (M−H)−.

Sources & evidence

ORD record
ord-34db6f6603ff4febb6a161752c9320a1
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

Loading…