2-chloro-N,N-dimethylacetamide → 2-{6-[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-3,4-dihydro-1H-isoquinolin-2-yl}-N,N-dimethyl-acetamide

HRID 1890055Notes

Reaction equation

HRID 1890055 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[C:14]2[N:15]([N:19]=[C:20]([NH:22][C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH2:29][NH:28][CH2:27][CH2:26]4)[N:21]=2)[CH:16]=[CH:17][CH:18]=1.Cl[CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:10])[F:11])=[CH:5][C:4]=1[C:13]1[C:14]2[N:15]([N:19]=[C:20]([NH:22][C:23]3[CH:24]=[C:25]4[C:30](=[CH:31][CH:32]=3)[CH2:29][N:28]([CH2:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36])[CH2:27][CH2:26]4)[N:21]=2)[CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 49838140[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-amine

Product 1

HCID 596125062-{6-[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-3,4-dihydro-1H-isoquinolin-2-yl}-N,N-dimethyl-acetamide

Procedure

2-{6-[8-(2-Methoxy-5-trifluoromethyl-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-3,4-dihydro-1H-isoquinolin-2-yl}-N,N-dimethyl-acetamide was prepared from [8-(2-methoxy-5-trifluoromethyl-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-amine (0.150 g, 0.341 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.053 mL, 0.512 mmol) in a manner analogous to Example 313 to give product (0.060 g, 34%). MP=99-102° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.51 (s, 1H), 8.79 (d, 1H), 7.95 (s, 1H), 7.80 (d, 1H), 7.62 (d, 1H), 7.38 (m, 3H), 7.05 (t, 1H), 6.90 (d, 1H), 3.85 (s, 3H), 3.52 (s, 2H), 3.28 (s, 2H), 3.05 (s, 3H), 2.82 (s, 3H), 2.70 (br m, 4H): MS=525 (MH)+.

Sources & evidence

ORD record
ord-0c32d1ccdc7b486789b610222382e2c6
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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