Dimethylamine → HCID 68891654, compound

HRID 1396576Notes

Reaction equation

HRID 1396576 reaction equation
[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15]([Br:19])=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][NH:21][CH3:22].CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.Cl>[CH2:1]([O:8][C:9]1[C:17]([F:18])=[CH:16][C:15]([Br:19])=[CH:14][C:10]=1[C:11]([N:21]([CH3:22])[CH3:20])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 688914765-Bromo-3-fluoro-2-(phenylmethoxy)benzoic acid

Product 1

HCID 68891654HCID 68891654, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

2-Benzyloxy-5-bromo-3-fluoro-benzoic acid (product from step 2) (0.2 g, 0.615 mmol) is dissolved in THF (10 ml) and treated with 2M dimethylamine in THF (0.308 ml), N-methylmorpholine (0.270 ml, 2.46 mmol) and HATU (0.234 g, 0.615 mmol) and stirred at room temperature overnight. The reaction mixture is diluted with 2M HCl and extracted with EtOAc (2×), the organic portions are combined washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting crude residue is dry loaded onto silica and purification by flash chromatography eluting with EtOAc affords the title compound as a white solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washthe organic portions are combined washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. dry with materialThe resulting crude residue is dry loaded onto silica and purification by flash chromatography
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-a4f0f271c05b4ac5b70ef256a3a404f4
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

Loading…