3-Aminopyridine → 5-Bromo-4-methyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

HRID 2204732Notes

Reaction equation

HRID 2204732 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:32][C:33]1[C:34]([CH3:50])=[CH:35][C:36]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[C:37]([CH:41]=1)[C:38](O)=[O:39]>CN(C)C=O>[Br:32][C:33]1[C:34]([CH3:50])=[CH:35][C:36]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[C:37]([CH:41]=1)[C:38]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:39]

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 666112185-Bromo-4-methyl-2-[(phenylmethyl)oxy]benzoic acid

Product 1

HCID 666112375-Bromo-4-methyl-2-[(phenylmethyl)oxy]-N-3-pyridinylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Aminopyridine (193 mg, 2.06 mmol), and HATU (852 mg, 2.24 mmol) were added to a solution of 5-bromo-4-methyl-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 9; 600 mg, 1.87 mmol) in N,N-dimethylformamide (10 ml). The reaction was stirred overnight and the solid was filtered. Solvent was removed in vacuo and water was added. The solid was filtered and washed with ethyl acetate (10 ml) to give a white solid. The products were combined to yield the title compound as an off white solid. 508 mg.

Workup

  1. filtrationthe solid was filtered
  2. customSolvent was removed in vacuo and water
  3. additionwas added
  4. filtrationThe solid was filtered
  5. washwashed with ethyl acetate (10 ml)
  6. customto give a white solid

Sources & evidence

ORD record
ord-4f3439be070648d38a4584de37fec8c5
Source dataset
uspto-grants-2016_06
Patent number
US09365551B2

Reaction notes

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