3-Aminopyridine → 3-Amino-6-bromo-N-pyridin-3-ylpyrazine-2-carboxamide

HRID 217771Notes

Reaction equation

HRID 217771 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.[NH2:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:1][C:2]1[C:3]([C:9]([NH:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[O:11])=[N:4][C:5]([Br:8])=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 100093-AminopyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 104021623-Amino-6-bromo-N-pyridin-3-ylpyrazine-2-carboxamideYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the product of step (iv) (100 g, 0.45 mol) in DMF (350 mL) was added TEA (129 mL, 0.91 mol) and 3-aminopyridine (42.3 g, 0.45 mol). HATU (174 g, 0.45 mol) was added to the solution portionwise. The suspension was filtered, washed with water and dried under a reduced pressure to afford the subtitle compound (v) as a yellow solid (105 g).

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with water
  3. customdried under a reduced pressure

Sources & evidence

ORD record
ord-27e1bc192fcf4223a0e32d07d6ecb165
Source dataset
uspto-grants-2012_06
Patent number
US08198285B2

Reaction notes

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