Acetic Acid → HCID 66606804, compound

HRID 1810268Notes

Reaction equation

HRID 1810268 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[C:23](=O)[CH3:24])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.[CH2:27]([NH2:29])[CH3:28].C([BH3-])#N.[Na+].C(O)(=O)C.C([O-])(O)=O.[Na+]>CO>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:21])([F:20])[F:22])=[CH:15][C:14]=2[CH:23]([NH:29][CH2:27][CH3:28])[CH3:24])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6341EthylamineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 66606374HCID 66606374, compound

Product 1

HCID 66606804HCID 66606804, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

(2′-Acetyl-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester (0.222 g, 0.61 mmol), ethylamine (2M in THF; 0.46 mL, 0.91 mmol), sodium cyanoborohydride (0.058 g, 0.91 mmol), and acetic acid (0.05 mL, 0.91 mmol) were combined in MeOH (2.2 mL) and heated to 60° C. overnight. Analytical LCMS showed starting material remained, so the reaction was stirred at 60° C. over the weekend. Once minimal starting material was seen by analytical LCMS, the mixture was cooled to room temperature and neutralized with saturated aqueous NaHCO3. The solution was extracted with CH2Cl2, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. extractionThe solution was extracted with CH2Cl2
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-27aafd4fd76841c6b1eee95931fd78b8
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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