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

HRID 605287

Reaction equation

HRID 605287 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.[CH3:30][N:31]([CH3:39])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH2:38])[CH:33]=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>[CH3:30][N:31]([CH3:39])[C:32]1[CH:33]=[C:34]([NH:38][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:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 178185-Amino-2-methylphenolHCID 76084N,N-dimethyl-m-phenylenediamineHCID 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 67040446N-(3-Dimethylamino-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 N,N-dimethyl-1,3-phenylenediamine according to the procedure from Example 137C substituting N,N-dimethyl-1,3-phenylenediamine 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 (45 mg, 52%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 10.33 (s, 1 H), 9.99 (s, 1 H), 9.11 (dd, J=4.41, 1.84 Hz, 1 H), 8.96 (dd, J=8.46, 1.84 Hz, 1 H), 8.63 (s, 1 H), 8.01 (d, J=1.84 Hz, 1 H), 7.82 (dd, J=8.46, 1.84 Hz, 1 H), 7.70 (dd, J=8.09, 4.41 Hz, 1 H), 7.36-7.43 (m, 2 H), 7.10-7.20 (m, 3 H), 6.97-7.04 (m, 3 H), 6.48 (td, J=4.50, 2.39 Hz, 1 H), 3.77 (s, 3 H), 2.88 (s, 6 H); MS (ESI+) m/z 523.5 (M+H)−, (ESI−) m/z 521.2 (M−H)−.

Sources & evidence

ORD record
ord-ff6af424ed37488389c031e7017724a0
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Linked notes

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