2-chloro-N,N-dimethylacetamide → HCID 59612593, compound

HRID 1890050Notes

Reaction equation

HRID 1890050 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([N:14]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)[CH:19]=4)[N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[C:4]([O:30][CH3:31])[CH:3]=1.Cl[CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[N:10]([N:14]=[C:15]([NH:17][C:18]4[CH:19]=[C:20]([CH:24]5[CH2:25][CH2:26][N:27]([CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[CH2:28][CH2:29]5)[CH:21]=[CH:22][CH:23]=4)[N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[C:4]([O:30][CH3:31])[CH:3]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 67481498HCID 67481498, compound

Product 1

HCID 59612593HCID 59612593, compound

Procedure

2-(4-{3-[8-(4-Chloro-2-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidin-1-yl)-N,N-dimethyl-acetamide was prepared from [8-(4-chloro-2-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(3-piperidin-4-yl-phenyl)-amine (0.047 g, 0.110 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.017 mL, 0.160 mmol) in a manner analogous to Example 313 to give product (0.012 g, 21%). MP=79-82° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.59 (s, 1H), 8.77 (d, 1H), 7.60 (m, 3H), 7.45 (d, 1H), 7.25 (s, 1H), 7.15 (m, 2H), 7.05 (m, 1H), 6.75 (d, 1H), 3.78 (s, 3H), 3.15 (s, 2H), 3.05 (s, 3H), 2.95 (m, 2H), 2.80 (s, 3H), 2.35 (m, 1H), 2.15 (m, 2H), 1.65 (m, 4H): MS=520 (MH)+.

Sources & evidence

ORD record
ord-02739a460d2f4feab218d54a17344f8c
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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