2-chloro-N,N-dimethylacetamide → HCID 59612553, compound

HRID 1890099Notes

Reaction equation

HRID 1890099 reaction equation
[F:1][CH:2]([F:35])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([F:13])[F:12])=[CH:7][C:6]=1[C:14]1[C:15]2[N:16]([N:20]=[C:21]([NH:23][C:24]3[CH:34]=[CH:33][C:27]4[CH2:28][CH2:29][NH:30][CH2:31][CH2:32][C:26]=4[CH:25]=3)[N:22]=2)[CH:17]=[CH:18][CH:19]=1.Cl[CH2:37][C:38]([N:40]([CH3:42])[CH3:41])=[O:39]>>[F:35][CH:2]([F:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([F:13])[F:12])=[CH:7][C:6]=1[C:14]1[C:15]2[N:16]([N:20]=[C:21]([NH:23][C:24]3[CH:34]=[CH:33][C:27]4[CH2:28][CH2:29][N:30]([CH2:37][C:38]([N:40]([CH3:42])[CH3:41])=[O:39])[CH2:31][CH2:32][C:26]=4[CH:25]=3)[N:22]=2)[CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 59612365HCID 59612365, compound

Product 1

HCID 59612553HCID 59612553, compound

Procedure

2-(7-{8-[2-(2,2-difluoro-ethoxy)-5-difluoromethyl-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino}-1,2,4,5-tetrahydro-3-benzazepin-3-yl)-N,N-dimethyl-acetamide was prepared from {8-[2-(2,2-difluoro-ethoxy)-5-difluoromethyl-phenyl]-[1,2,4]triazolo[1,5-a]pyridin-2-yl}-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-amine (0.065 g, 0.130 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.045 mL, 0.200 mmol) in a manner analogous to Example 313 to give product (0.045 g, 59%). MP=200-201° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.49 (s, 1H), 8.78 (d, 1H), 7.90 (s, 1H), 7.65 (m, 2H), 7.42 (m, 3H), 7.05 (m, 2H), 7.02 (br m, 1H), 6.30 (br m, 1H), 4.42 (m, 2H), 3.22 (s, 2H), 3.05 (s, 3H), 2.80 (m, 7H), 2.60 (m, 4H). MS=571 (MH)+.

Sources & evidence

ORD record
ord-e41ce2bb0a454c39936107033d5ad7d6
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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