2-Amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-ol → 2-[5-Chloro-4-(4-methoxy-2-pyrazol-1-yl-phenylamino)-pyrimidin-2-ylamino]-6,7,8,9-tetrahydro-5h-benzocyclohepten-7-ol
Reaction equation
[Cl:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[N:35]2[CH:39]=[CH:38][CH:37]=[N:36]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][CH2:17][CH:16](N4CCOCC4)[CH2:15][CH2:14][C:13]=3[CH:25]=2)=[N:6][CH:7]=1.NC1C=CC2CCC([OH:51])CCC=2C=1>>[Cl:1][C:2]1[C:3]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[N:35]2[CH:39]=[CH:38][CH:37]=[N:36]2)=[N:4][C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]3[CH2:18][CH2:17][CH:16]([OH:51])[CH2:15][CH2:14][C:13]=3[CH:25]=2)=[N:6][CH:7]=1Participants
Reactant 2
Product 1
Procedure
The desired product was also isolated from Example 622, as starting material 7-Morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclo hepten-2-ylamine of Example 622 was contaminated with a small amount of its respective alcohol, 2-Amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-ol. The product 2-[5-Chloro-4-(4-methoxy-2-pyrazol-1-yl-phenylamino)-pyrimidin-2-ylamino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-ol was isolated as a lyophylate (10%); 1H NMR (400 MHz, DMSO-d6) δ 9.79 (s, 1H), 9.23 (s, 1H), 8.26 (s, 1H), 8.09 (s, 1H), 8.02 (d, J=8.62 Hz, 1H), 7.83 (s, 1H), 7.35 (s, 1H), 7.23 (s, 1H), 7.19 (d, J=7.95 Hz, 1H), 7.00 (d, J=8.98 Hz, 1H), 6.90 (d, J=8.20 Hz, 1H), 6.54 (s, 1H), 3.87 (s, 3H), 3.71 (bm, 1H), 2.68 (m, 1H), 2.5 (DMSO-d+H), 1.86 (m, 2H), 1.30 (m, 2H); MS (m/e) 477.43 (M+H).
Sources & evidence
- ORD record
- ord-9063e1be980143d6a32ddd19f7cb5e3f
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08552186B2
Reaction notes
Loading…