Benzene, 1-bromo-3-(methylsulfonyl)- → (3-Methanesulfonyl-phenyl)-[5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine

HRID 472357Notes

Reaction equation

HRID 472357 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:23]=1>>[CH3:31][S:28]([C:24]1[CH:23]=[C:22]([NH:20][C:18]2[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=4)[N:16]3[N:17]=2)[CH:27]=[CH:26][CH:25]=1)(=[O:30])=[O:29]

Participants

3

Reactant 2

HCID 2757146Benzene, 1-bromo-3-(methylsulfonyl)-HCID 674790495-(4-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 59612548(3-Methanesulfonyl-phenyl)-[5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amineYield 40.9%

Procedure

(3-Methanesulfonyl-phenyl)-[5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75 mg, 0.26 mmol) and 1-bromo-3-methanesulfonyl benzene (73 mg, 0.29 mmol) in a manner analogous to Example 77 to yield (3-methanesulfonyl-phenyl)-[5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine (47 mg, 39%) as a white powder following trituration with methanol. MP=279° C. 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 10.18 (s, 1H), 8.49 (s, 1H), 8.37 (d, J=8.0 Hz, 2H), 8.15 (d, J=8.0 Hz, 2H), 7.70-7.81 (m, 3H), 7.55 (t, J=17.4 Hz, 8.0 Hz, 1H), 7.36-7.45 (m, 2H), 3.30 (s, 3H), 3.17 (s, 3H). MS=443 (MH)+.

Sources & evidence

ORD record
ord-d04feadcd7ab4d22818e98d364d9b192
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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