Aniline → HCID 117771515, compound

HRID 2201516Notes

Reaction equation

HRID 2201516 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:16]([OH:18])=O)=[N:11][C:12]([Br:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(ON1N=N[C:29]2[CH:30]=[CH:31][CH:32]=[N:33][C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:43]1(N)C=CC=C[CH:44]=1>CN(C=O)C>[CH2:32]([NH:33][C:16](=[O:18])[C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=[C:12]([Br:15])[N:11]=1)[C:31]1[CH:44]=[CH:43][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 87131485HCID 87131485, compound

Product 1

HCID 117771515HCID 117771515, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(benzyloxy)-6-bromopicolinic acid (0.50 g, 1.62 mmol) and HATU (1.23 g, 3.24 mmol) in DMF (5 mL) was added phenylamine (0.52 g, 4.87 mmol) dropwise. After stirring at room temperature overnight, the mixture was concentrated and the residue was diluted with water and extracted with EtOAc. The combined organic phase was washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash gel chromatography (DCM:MeOH=50:1) to afford the product of N-benzyl-3-(benzyloxy)-6-bromopicolinamide (0.60 g, yield: 93.2%). 1H-NMR (CDCl3, 400 MHz) δ 7.79 (br s, 1H), 7.38˜7.41 (m, 3H), 7.19˜7.32 (m, 9H), 5.18 (s, 2H), 4.58 (d, J=5.6 Hz, 2H). MS (M+H)+: 397/399.

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash gel chromatography (DCM:MeOH=50:1)

Sources & evidence

ORD record
ord-e087835338984d098a7b07d2fdf25c36
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

Loading…