2-chloro-N,N-dimethylacetamide → HCID 49839723, compound

HRID 1890062Notes

Reaction equation

HRID 1890062 reaction equation
[F: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][C:21]([CH:24]5[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.Cl[CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33]>>[F: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][C:21]([CH:24]5[CH2:29][CH2:28][N:27]([CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33])[CH2:26][CH2:25]5)=[CH:20][CH:19]=4)[N:16]=3)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 59612429HCID 59612429, compound

Product 1

HCID 49839723HCID 49839723, compound

Procedure

2-(4-{4-[8-(4-Fluoro-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidin-1-yl)-N,N-dimethyl-acetamide was prepared from [8-(4-fluoro-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine (0.092 g, 0.240 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.037 mL, 0.360 mmol) in a manner analogous to Example 313 to give product (0.035 g, 31%). MP=209-212° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.64 (s, 1H), 8.79 (d, 1H), 8.22 (m, 2H), 7.82 (d, 1H), 7.60 (d, 2H), 7.35 (m, 2H), 7.12 (m, 3H), 3.13 (s, 2H), 3.05 (s, 3H), 2.92 (m, 2H), 2.82 (s, 3H), 2.40 (m, 1H), 2.12 (m, 2H), 1.64-1.70 (br m, 4H). MS=473 (MH)+.

Sources & evidence

ORD record
ord-ffd619789aeb4819834c4787d9a65578
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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