2-chloro-N,N-dimethylacetamide → HCID 59612587, compound

HRID 1890079Notes

Reaction equation

HRID 1890079 reaction equation
[CH3:1][N:2]([CH3:31])[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[CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35]>>[CH3:1][N:2]([CH3:31])[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]([CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[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 59612573HCID 59612573, compound

Product 1

HCID 59612587HCID 59612587, compound

Procedure

2-(4-{4-[8-(3-Dimethylamino-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidin-1-yl)-N,N-dimethyl-acetamide was prepared from [8-(3-dimethylamino-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine (0.100 g, 0.242 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.037 mL, 0.364 mmol) in a manner analogous to Example 313 to give product (0.060 g, 50%). MP=100-104° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.56 (s, 1H), 8.75 (d, 1H), 7.82 (d, 1H), 7.62 (d, 2H), 7.50 (s, 1H), 7.32 (m, 2H), 7.15 (m, 3H), 6.80 (d, 1H), 3.15 (s, 2H), 3.05 (s, 3H), 3.00 (s, 6H), 2.95 (m, 2H), 2.82 (s, 3H), 2.45 (m, 1H), 2.15 (m, 2H), 1.65 (m, 4H). MS=498 (MH)+.

Sources & evidence

ORD record
ord-ca8f2e80c0ae4d498769298646a90f8c
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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