4-Aminobenzonitrile → N-(4-Cyano-phenyl)-4-(4-methoxy-phenylsulfanyl)-3-(pyrido[2,3-d]pyrimidin-4-ylamino)-benzamide
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:38]=[CH:37][C:34]([C:35]#[N:36])=[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:35]([C:34]1[CH:37]=[CH:38][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:36]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The product from Example 260B was reacted with 4-aminobenzonitrile according to the procedure from Example 137C substituting 4-aminobenzonitrile 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 (51.5 mg, 62%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 11.11 (s, 1 H), 10.62 (s, 1 H), 9.11 (s, 1 H), 9.00 (d, J=5.51 Hz, 1 H), 8.57-8.80 (m, 1 H), 7.97 (d, J=8.82 Hz, 2 H), 7.68-7.90 (m, J=8.82 Hz, 3 H), 7.38-7.52 (m, 2 H), 6.88-7.12 (m, 3 H), 6.45-6.71 (m, 1 H), 3.77 (s, 3 H).
Sources & evidence
- ORD record
- ord-3ff5c184f3644084ac98dde30a2822e7
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07910595B2
Reaction notes
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