N-(3-Aminopyridin-2-yl)-N-methylmethanesulfonamide → N-[3-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-pyridin-2-yl]-N-methyl-methanesulfonamide

HRID 472374Notes

Reaction equation

HRID 472374 reaction equation
[NH2:1][C:2]1[C:3]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1.Br[C:15]1[C:16]2[N:17]([N:21]=[C:22]([Cl:24])[N:23]=2)[CH:18]=[CH:19][CH:20]=1>>[Cl:24][C:22]1[N:23]=[C:16]2[C:15]([NH:1][C:2]3[C:3]([N:8]([CH3:13])[S:9]([CH3:12])(=[O:11])=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=3)=[CH:20][CH:19]=[CH:18][N:17]2[N:21]=1

Participants

3

Reactant 2

HCID 57416061N-(3-Aminopyridin-2-yl)-N-methylmethanesulfonamideHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 67481475N-[3-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-pyridin-2-yl]-N-methyl-methanesulfonamide

Procedure

N-[3-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylamino)-pyridin-2-yl]-N-methyl-methanesulfonamide was prepared from N-(3-amino-pyridin-2-yl)-N-methyl-methanesulfonamide (238.0 mg, 1.183 mmol) and 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine (250.0 mg, 1.075 mmol) in a manner analogous to Example 2d. Product isolated as a pale yellow foam (0.185 g, 48%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.18-8.15 (m, 1H), 8.11 (d, J=6.8 Hz, 1H), 7.81 (d, J=8.0 Hz, 1H), 7.50 (s, 1H), 7.32-7.25 (m, 1H), 7.17 (d, J=7.5 Hz, 1H), 6.93 (t, J=7.3 Hz, 1H), 3.31 (s, 3H), 3.07 (s, 3H). MS=353, 355 (MH)+.

Sources & evidence

ORD record
ord-025e25c1000a42058e27562585f65cde
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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