2-chloro-N,N-dimethylacetamide → HCID 59612384, compound

HRID 1890052Notes

Reaction equation

HRID 1890052 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:28]=[CH:27][C:26]([CH:29]4[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]4)=[CH:25][CH:24]=3)[N:21]=2)[CH:16]=[CH:17][CH:18]=1.Cl[CH2:36][C:37]([N:39]([CH3:41])[CH3:40])=[O:38]>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:11])([F:10])[F:12])=[CH:5][C:4]=1[C:13]1[C:14]2[N:15]([N:19]=[C:20]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([CH:29]4[CH2:34][CH2:33][N:32]([CH2:36][C:37]([N:39]([CH3:41])[CH3:40])=[O:38])[CH2:31][CH2:30]4)=[CH:25][CH:24]=3)[N:21]=2)[CH:16]=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 59612622HCID 59612622, compound

Product 1

HCID 59612384HCID 59612384, compound

Procedure

2-(4-{4-[8-(2-Methoxy-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-methoxy-5-trifluoromethyl-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine (0.150 g, 0.321 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.049 mL, 0.481 mmol) in a manner analogous to Example 313 to give product (0.060 g, 34%). MP=109-112° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.55 (s, 1H), 8.79 (d, 1H), 7.95 (s, 1H), 7.82 (d, 1H), 7.62 (d, 1H), 7.55 (d, 2H), 7.35 (d, 1H), 7.05 (m, 3H), 3.85 (s, 3H), 3.15 (s, 2H), 3.05 (s, 3H), 2.95 (m, 2H), 2.82 (s, 3H), 2.40 (m, 1H), 2.10 (m, 2H), 1.65 (br m, 4H): MS=553 (MH)+.

Sources & evidence

ORD record
ord-4bce5a73577e4e829ad1235850f9ffe6
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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