Ethanamine, 2,2,2-trifluoro- → HCID 67216406, compound

HRID 1051849Notes

Reaction equation

HRID 1051849 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[O:11][CH3:12].[F:13][C:14]([F:18])([F:17])[CH2:15][NH2:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C(=O)(O)[O-].[Na+]>C1COCC1.O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:16][CH2:15][C:14]([F:18])([F:17])[F:13])=[O:8])=[CH:4][C:3]=1[O:11][CH3:12]

Participants

8

Reactant 5

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 162158674-Bromo-3-methoxybenzoic acid

Product 1

HCID 67216406HCID 67216406, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 4-bromo-3-methoxybenzoic acid (2.0 g) in THF (100 mL) was added 2,2,2-trifluoroethylamine (1.26 g), HATU (3.87 g), and DIPEA (1.7 ml). The mixture was stirred at room temperature for 12 h. Water (350 ml) and saturated sodium bicarbonate solution (350 ml) were added. The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 2.57 g of the title compound.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (sodium sulfate)
  4. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-ec1e1e606a834b918bc2c0e0f6efcafd
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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