N-(3-Bromophenyl)acetamide → HCID 59612376, compound

HRID 472551Notes

Reaction equation

HRID 472551 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH2:20])[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:22]1[CH:23]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:25]=[CH:26][CH:27]=1>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]3[N:13]([N:17]=[C:18]([NH:20][C:22]4[CH:23]=[C:24]([NH:28][C:29](=[O:31])[CH3:30])[CH:25]=[CH:26][CH:27]=4)[N:19]=3)[CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

Participants

3

Reactant 2

HCID 12123N-(3-Bromophenyl)acetamideHCID 575023768-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine

Product 1

HCID 59612376HCID 59612376, compound

Procedure

N-{3-[8-(4-Methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino]-phenyl}-acetamide was prepared from 8-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (70.6 mg, 0.245 mmol) and N-(3-bromo-phenyl)-acetamide (52.4 mg, 0.245 mmol) in a manner analogous to Example 2d. Product isolated as a white lyophilate (19 mg, 18%). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.89 (s, 1H), 9.77 (s, 1H), 8.83 (d, J=6.5 Hz, 1H), 8.46 (d, J=8.4 Hz, 2H), 8.07 (d, J=8.6 Hz, 2H), 7.99-7.95 (m, 2H), 7.40 (d, J=8.0 Hz, 1H), 7.21-7.12 (m, 3H), 3.29 (s, 3H), 2.06 (s, 3H). MS=422 (MH)+.

Workup

  1. customProduct isolated as a white lyophilate (19 mg, 18%)

Sources & evidence

ORD record
ord-c737fdfb6f0a4350a002d4e7f354779f
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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