N-bromobutanimide → HCID 24762945, compound

HRID 253949Notes

Reaction equation

HRID 253949 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH:13]=[N:12][N:11]=[C:10]1[C:14]1[C:15]([NH2:20])=[N:16][CH:17]=[CH:18][N:19]=1.C1C(=O)N([Br:28])C(=O)C1.C([O-])(O)=O.[Na+]>CC#N>[Br:28][C:18]1[N:19]=[C:14]([C:10]2[N:9]([C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=3[F:1])[CH:13]=[N:12][N:11]=2)[C:15]([NH2:20])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 58179594HCID 58179594, compound

Product 1

HCID 24762945HCID 24762945, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(4-(2,3-difluorophenyl)-4H-1,2,4-triazol-3-yl)pyrazin-2-amine (700 mg, 2.55 mmol) in dry CH3CN (20 mL) was added NBS (550 mg, 3.09 (mmol). The solution was stirred at RT for 1 h and poured into saturated NaHCO3 solution. The precipitate was collected by vacuum filtration and washed with water (700 mg, 78%) to produce 5-bromo-3-(4-(2,3-difluorophenyl)-4H-1,2,4-triazol-3-yl)pyrazin-2-amine [LC-MS m/e=353/354.6 (M+H)]. Using the same procedure, 5-bromo-3-(4-(2,3-dichlorophenyl)-4H-1,2,4-triazol-3-yl)pyrazin-2-amine, 5-bromo-3-(4-(3-chloro-2-fluorophenyl)-4H-1,2,4-triazol-3-yl)pyrazin-2-amine, 5-bromo-3-(4-(2,3-difluorophenyl)-4H-1,2,4-triazol-3-yl)pyridin-2-amine, 5-bromo-3-(4-(2,3-dichlorophenyl)-4H-1,2,4-triazol-3-yl)pyridin-2-amine, and 5-bromo-3-(4-(3-chloro-2-fluorophenyl)-4H-1,2,4-triazol-3-yl)pyridin-2-amine can be produced from 3-(4-(2,3-dichlorophenyl)-4H-1,2,4-triazol-3-yl)pyrazin-2-amine, 3-(4-(3-chloro-2-fluorophenyl)-4H-1,2,4-triazol-3-yl)pyrazin-2-amine, 3-(4-(2,3-difluorophenyl)-4H-1,2,4-triazol-3-yl)pyridin-2-amine, 3-(4-(2,3-dichlorophenyl)-4H-1,2,4-triazol-3-yl)pyridin-2-amine, and 3-(4-(3-chloro-2-fluorophenyl)-4H-1,2,4-triazol-3-yl)pyridin-2-amine, respectively.

Workup

  1. filtrationThe precipitate was collected by vacuum filtration
  2. washwashed with water (700 mg, 78%)

Sources & evidence

ORD record
ord-f381d6100d4440ff899f467e98185358
Source dataset
uspto-grants-2011_01
Patent number
US07872031B2

Reaction notes

Loading…