2,2,2-Trifluoroethylamine hydrochloride → HCID 86633168, compound

HRID 1919946Notes

Reaction equation

HRID 1919946 reaction equation
Cl.[F:2][C:3]([F:7])([F:6])[CH2:4][NH2:5].C([O-])(=O)C.[Na+].[CH3:13][O:14][C:15](=[O:37])[CH2:16][C:17]1[CH:18]=[C:19]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][C:26]=2[CH:35]=O)[C:20]([O:23][CH3:24])=[CH:21][CH:22]=1.C([BH3-])#N.[Na+]>CO>[CH3:13][O:14][C:15](=[O:37])[CH2:16][C:17]1[CH:18]=[C:19]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:27][C:26]=2[CH2:35][NH:5][CH2:4][C:3]([F:7])([F:6])[F:2])[C:20]([O:23][CH3:24])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86633167(2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

Product 1

HCID 86633168HCID 86633168, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2,2,2-Trifluoroethylamine hydrochloride (0.101 g, 0.71 mmol) was treated with sodium acetate (0.061 g, 0.71 mmol) in MeOH (1 mL) with heating and sonication. (2′-Formyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.207 g, 0.59 mmol) in MeOH (2 mL) was added, followed by sodium cyanoborohydride (0.069 g, 1.06 mmol), and the reaction was stirred at room temperature for 1 hour. Once no starting material was seen by analytical LCMS, the mixture was quenched with H2O and extracted twice with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. temperaturewith heating
  2. customsonication
  3. customthe mixture was quenched with H2O
  4. extractionextracted twice with CH2Cl2
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4eaeb8810c8c43c6bec2f56cd5aecaf7
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

Loading…