6-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline → 6-[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester
Reaction equation
Cl[C:2]1[N:22]=[C:5]2[C:6]([C:10]3[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=3[O:20][CH3:21])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:23]([O:27][C:28]([N:30]1[CH2:39][CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[C:35]([NH2:40])[CH:36]=2)[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>>[C:23]([O:27][C:28]([N:30]1[CH2:39][CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[C:35]([NH:40][C:2]3[N:22]=[C:5]4[C:6]([C:10]5[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=5[O:20][CH3:21])=[CH:7][CH:8]=[CH:9][N:4]4[N:3]=3)[CH:36]=2)[CH2:31]1)=[O:29])([CH3:26])([CH3:24])[CH3:25]Participants
3
Reactant 2
Product 1
Procedure
6-[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester was prepared from 2-chloro-8-(2-methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine (0.250 g, 0.763 mmol) and 6-amino-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (0.284 g, 1.14 mmol) in a manner analogous to Example 311a and 311b to give product. MP=86-90° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.59 (s, 1H), 8.78 (d, 1H), 7.95 (s, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.45 (m, 2H), 7.38 (d, 1H), 7.05 (m, 2H), 4.40 (m, 2H), 3.85 (s, 3H), 3.52 (m, 2H), 2.75 (m, 2H), 1.42 (s, 9H): MS=540 (MH)+.
Workup
- customto give product
Sources & evidence
- ORD record
- ord-b229b6c31246447b844560a9c8725dc2
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08633173B2
Reaction notes
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