2-chloro-N,N-dimethylacetamide → HCID 49838008, compound

HRID 1890049Notes

Reaction equation

HRID 1890049 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([N:14]=[C:15]([NH:17][C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[CH2:24][NH:23][CH2:22][CH2:21]5)[N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[C:4]([O:28][CH3:29])[CH:3]=1.Cl[CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([N:14]=[C:15]([NH:17][C:18]4[CH:19]=[C:20]5[C:25](=[CH:26][CH:27]=4)[CH2:24][N:23]([CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[CH2:22][CH2:21]5)[N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[C:4]([O:28][CH3:29])[CH:3]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 67481494HCID 67481494, compound

Product 1

HCID 49838008HCID 49838008, compound

Procedure

2-{6-[8-(4-Chloro-2-methoxy-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-(4-chloro-2-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(1,2,3,4-tetrahydro-isoquinolin-6-yl)-amine (0.077 g, 0.190 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.029 mL, 0.284 mmol) in a manner analogous to Example 313 to give product (0.015 g, 16%). MP=103-106° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.53 (s, 1H), 8.78 (d, 1H), 7.58 (m, 2H), 7.42 (m, 2H), 7.25 (s, 1H), 7.15 (d, 1H), 7.05 (t, 1H), 6.92 (d, 1H), 3.78 (s, 3H), 3.54 (s, 2H), 3.28 (s, 2H), 3.05 (s, 3H), 2.85 (s, 3H), 2.78 (m, 2H), 2.70 (m, 2H): MS=491 (MH)+.

Sources & evidence

ORD record
ord-21433e8b73f846dd9c75bb1f18bca5ed
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

Loading…