Triethylamine → HCID 68505802, compound

HRID 1715421Notes

Reaction equation

HRID 1715421 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:4][C:3]=1[CH:18]=O.CCN(CC)CC.[CH:27]1([NH2:30])[CH2:29][CH2:28]1.[BH4-].[Na+].C([O-])(O)=O.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[CH2:12][C:13]([F:16])([F:15])[F:14])=[CH:4][C:3]=1[CH2:18][NH:30][CH:27]1[CH2:29][CH2:28]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86622960HCID 86622960, compound

Product 1

HCID 68505802HCID 68505802, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-[2-(4-chloro-3-formyl-phenyl)-ethyl]-3,3,3-trifluoro-propionamide (175 mg, 0.596 mmol), Et3N (0.125 mL, 0.896 mmol) and cyclopropylamine (0.063 mL, 0.90 mmol) in MeOH (2.00 mL) was heated to reflux for 4 h. The mixture was allowed to cool to rt, and NaBH4 (56.4 mg, 1.49 mmol) was added in portions. The mixture was stirred for 1 h, and aq. sat. NaHCO3 was added. The mixture was extracted with EtOAc several times, and the combined org. extracts were washed with brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (CH2Cl2/MeOH 95:5) yielded the title compound (130 mg, 65%). LC-MS: tR=0.65 min; ES+: 335.12.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. extractionThe mixture was extracted with EtOAc several times
  4. washextracts were washed with brine
  5. dry with materiallayer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customPurification of the residue by FC (CH2Cl2/MeOH 95:5)

Sources & evidence

ORD record
ord-a03d663cf42c40258f350b6caf27204a
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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