6-(2-amino-5-chlorophenyl)-N-(3-(trifluoromethyl)benzyl)pyrimidin-4-amine → 3-((3-((4-Chloro-2-(6-((3-(trifluoromethyl)benzyl)amino)pyrimidin-4-yl)phenyl)carbamoyl)benzyl)thio)propanoic acid
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=2)[CH:10]=1.N1(C2C=CC(N[C:40]([C:42]3[CH:43]=[C:44]([CH:52]=[CH:53][CH:54]=3)[CH2:45][S:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])=[O:41])=C(C3C=C(NCC4C=CC=C(C)C=4)N=CN=3)C=2)CCCCC1.NC1C=CC(N2CCCCC2)=CC=1C1N=CN=C(NCC2C=CC=C(C)C=2)C=1>>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:40]([C:42]2[CH:43]=[C:44]([CH:52]=[CH:53][CH:54]=2)[CH2:45][S:46][CH2:47][CH2:48][C:49]([OH:51])=[O:50])=[O:41])=[C:3]([C:9]2[CH:10]=[C:11]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:25])([F:24])[F:26])[CH:18]=3)[N:12]=[CH:13][N:14]=2)[CH:4]=1Participants
4
Reactant 3
Product 1
Procedure
This compound was prepared from 6-(2-amino-5-chlorophenyl)-N-(3-(trifluoromethyl)benzyl)pyrimidin-4-amine 65b using the procedure described for the preparation of 3-((3-((4-(piperidin-1-yl)-2-(6-((3-methylbenzyl)amino)pyrimidin-4-yl)phenyl)carbamoyl)benzyl)thio)propanoic acid 3.2 from 6-(2-amino-5-(piperidin-1-yl)phenyl)-N-(3-methylbenzyl)pyrimidin-4-amine 3.2b. 1H-NMR (400 MHz, DMSO-d6, ppm): δ 8.79 (s, 1H), 8.48 (s, 1H), 7.91 (s, 1H), 7.81 (d, J=5.7 Hz, 2H), 7.63 (s, 1H), 7.56 (m, 6H), 7.09 (s, 1H), 4.74 (s, 2H), 3.88 (s, 2H), 2.57 (d, J=4.8 Hz, 2H). MS (ES, m/z): 601 [M+H]+.
Sources & evidence
- ORD record
- ord-a491027ac0a340c0bb667cfe8d2c5c1c
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09301951B2
Reaction notes
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