2-chloro-N,N-dimethylacetamide → HCID 59612607, compound

HRID 1890064Notes

Reaction equation

HRID 1890064 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([CH:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.Cl[CH2:32][C:33]([N:35]([CH3:37])[CH3:36])=[O:34]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]3[N:11]([N:15]=[C:16]([NH:18][C:19]4[CH:24]=[CH:23][C:22]([CH:25]5[CH2:30][CH2:29][N:28]([CH2:32][C:33]([N:35]([CH3:37])[CH3:36])=[O:34])[CH2:27][CH2:26]5)=[CH:21][CH:20]=4)[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 59612407HCID 59612407, compound

Product 1

HCID 59612607HCID 59612607, compound

Procedure

2-(4-{4-[8-(3-Methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidin-1-yl)-N,N-dimethyl-acetamide was prepared from [8-(3-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine (0.150 g, 0.375 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.057 mL, 0.563 mmol) in a manner analogous to Example 313 to give product (0.065 g, 36%). MP=178-179° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.61 (s, 1H), 8.78 (d, 1H), 7.85 (d, 1H), 7.80 (s, 1H), 7.65 (m, 3H), 7.40 (m, 1H), 7.15 (m, 3H), 7.05 (m, 1H), 3.86 (s, 3H), 3.15 (s, 2H), 3.05 (s, 3H), 2.92 (m, 2H), 2.85 (s, 3H), 2.40 (m, 1H), 2.10 (m, 2H), 1.65 (m, 4H). MS=485 (MH)+.

Sources & evidence

ORD record
ord-af75364d8be5429b9786d4c4d82fafd5
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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