2-chloro-N,N-dimethylacetamide → HCID 49839609, compound

HRID 1890047Notes

Reaction equation

HRID 1890047 reaction equation
[F:1][CH:2]([F:37])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[C:15]1[C:16]2[N:17]([N:21]=[C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[CH:27][CH:26]=3)[N:23]=2)[CH:18]=[CH:19][CH:20]=1.Cl[CH2:39][C:40]([N:42]([CH3:44])[CH3:43])=[O:41]>>[F:37][CH:2]([F:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:12])([F:13])[F:14])=[CH:7][C:6]=1[C:15]1[C:16]2[N:17]([N:21]=[C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH:31]4[CH2:32][CH2:33][N:34]([CH2:39][C:40]([N:42]([CH3:44])[CH3:43])=[O:41])[CH2:35][CH2:36]4)=[CH:27][CH:26]=3)[N:23]=2)[CH:18]=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 86648364HCID 86648364, compound

Product 1

HCID 49839609HCID 49839609, compound

Procedure

2-[4-(4-{8-[2-(2,2-Difluoro-ethoxy)-5-trifluoromethyl-phenyl]-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino}-phenyl)-piperidin-1-yl]-N,N-dimethyl-acetamide was prepared from {8-[2-(2,2-difluoro-ethoxy)-5-trifluoromethyl-phenyl]-[1,2,4]-triazolo[1,5-a]pyridin-2-yl}-(4-piperidin-4-yl-phenyl)-amine (0.067 g, 0.130 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.020 mL, 0.190 mmol) in a manner analogous to Example 313 to give product (0.020 g, 26%). MP=98-101° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.54 (s, 1H), 8.80 (d, 1H), 8.08 (s, 1H), 7.82 (d, 1H), 7.68 (d, 1H), 7.58 (m, 2H), 7.45 (d, 1H), 7.10 (m, 3H), 6.30 (br m, 1H), 4.49 (m, 2H), 3.15 (s, 2H), 3.05 (s, 3H), 2.95 (m, 2H), 2.82 (s, 3H), 2.38 (m, 1H), 2.12 (m, 2H), 1.55-1.72 (br m, 4H): MS=603 (MH)+.

Sources & evidence

ORD record
ord-e60830efa65f475b987fc342b57db89d
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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