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

HRID 472614Notes

Reaction equation

HRID 472614 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:30]=[C:17]4[C:18]([C:22]5[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=5)=[CH:19][CH:20]=[CH:21][N:16]4[N:15]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.Cl[CH2:32][C:33]([N:35]([CH3:37])[CH3:36])=[O:34]>>[C:26]([C:25]1[CH:24]=[CH:23][C:22]([C:18]2[C:17]3[N:16]([N:15]=[C:14]([NH:13][C:10]4[CH:9]=[CH:8][C:7]([CH:4]5[CH2:5][CH2:6][N:1]([CH2:32][C:33]([N:35]([CH3:37])[CH3:36])=[O:34])[CH2:2][CH2:3]5)=[CH:12][CH:11]=4)[N:30]=3)[CH:21]=[CH:20][CH:19]=2)=[CH:29][CH:28]=1)#[N:27]

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 49839725HCID 49839725, compound

Product 1

HCID 498397222-(4-{4-[8-(4-Cyano-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidin-1-yl)-N,N-dimethyl-acetamide

Procedure

2-(4-{4-[8-(4-Cyano-phenyl)-[1,2,4]-triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-piperidin-1-yl)-N,N-dimethyl-acetamide was prepared from 4-[2-(4-piperidin-4-yl-phenylamino)-[1,2,4]triazolo[1,5-a]pyridine-8-yl]benzonitrile (0.111 g, 0.281 mmol) and 2-chloro-N,N-dimethyl-acetamide (0.043 mL, 0.422 mmol) in a manner analogous to Example 313 to give product (0.060 g, 44%). MP=245-246° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.71 (s, 1H), 8.87 (d, 1H), 8.40 (d, 2H), 8.00 (m, 3H), 7.62 (d, 2H), 7.15 (m, 3H), 3.12 (s, 2H), 3.05 (s, 3H), 2.95 (m, 2H), 2.80 (s, 3H), 2.40 (m, 1H), 2.12 (m, 2H), 1.65 (m, 4H). MS=480 (MH)+.

Sources & evidence

ORD record
ord-bd9d4b0c618d4506b6ee077bb76769a5
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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