2-chloro-N,N-dimethylacetamide → 2-(4-{4-[8-(2-Fluoro-3-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidin-1-yl)-N,N-dimethyl-acetamide

HRID 472608Notes

Reaction equation

HRID 472608 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:11]2[N:12]([N:16]=[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)=[CH:22][CH:21]=3)[N:18]=2)[CH:13]=[CH:14][CH:15]=1.Cl[CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35]>>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]1[C:11]2[N:12]([N:16]=[C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH:26]4[CH2:27][CH2:28][N:29]([CH2:33][C:34]([N:36]([CH3:38])[CH3:37])=[O:35])[CH2:30][CH2:31]4)=[CH:22][CH:21]=3)[N:18]=2)[CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 59612444HCID 59612444, compound

Product 1

HCID 596123582-(4-{4-[8-(2-Fluoro-3-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidin-1-yl)-N,N-dimethyl-acetamide

Procedure

2-(4-{4-[8-(2-Fluoro-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-(2-fluoro-3-methoxy-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-yl]-(4-piperidin-4-yl-phenyl)-amine (0.150 g, 0.359 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.055 mL, 0.539 mmol) in a manner analogous to Example 313 to give product (0.075 g, 42%). MP=237-240° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.62 (s, 1H), 8.82 (d, 1H), 7.60 (m, 3H), 7.25 (m, 3H), 7.10 (m, 3H), 3.90 (s, 3H), 3.15 (s, 2H), 3.05 (s, 3H), 2.95 (m, 2H), 2.85 (s, 3H), 2.35 (m, 1H), 2.10 (m, 2H), 1.65 (m, 4H). MS=503 (MH)+.

Sources & evidence

ORD record
ord-4efee81c8ce84ee797d0fbbe3571cfbc
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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