Trifluoroacetic acid → HCID 86722597, compound

HRID 1503072Notes

Reaction equation

HRID 1503072 reaction equation
[NH2:1][C:2]([CH3:34])([CH3:33])[CH2:3][NH:4][C:5](=[O:32])[C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[CH:14]([C:19]2[CH:24]=[C:23]([Cl:25])[C:22]([Cl:26])=[C:21]([Cl:27])[CH:20]=2)[C:15]([F:18])([F:17])[F:16])=[CH:8][C:7]=1[C:28]([F:31])([F:30])[F:29].F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.[F:59][C:60]([F:65])([F:64])[C:61](O)=[O:62].CN1CCOCC1>CN(C=O)C>[CH3:33][C:2]([NH:1][C:61](=[O:62])[C:60]([F:65])([F:64])[F:59])([CH3:34])[CH2:3][NH:4][C:5](=[O:32])[C:6]1[CH:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[CH:14]([C:19]2[CH:24]=[C:23]([Cl:25])[C:22]([Cl:26])=[C:21]([Cl:27])[CH:20]=2)[C:15]([F:18])([F:16])[F:17])=[CH:8][C:7]=1[C:28]([F:31])([F:30])[F:29]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 86722598HCID 86722598, compoundHCID 178484293HCID 178484293, compound

Product 1

HCID 86722597HCID 86722597, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-N-(2-amino-2-methylpropyl)-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)-2-(trifluoromethyl)benzamide (155 mg, 0.283 mmol), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU) (118 mg, 0.311 mmol), and 2,2,2-trifluoroacetic acid (0.026 mL, 0.340 mmol) in DMF (1 mL) was—added N-methylmorpholine (0.062 mL, 0.566 mmol). The mixture was stirred at ambient temperature for 18 h, —then partitioned between water and EtOAc. The organic phase was washed with water and—brine, —dried (sodium sulfate) and concentrated—under reduced pressure. Purification by column chromatography eluting with EtOAc in hexanes (10%-100%)—afforded the title compound as a yellow oil (26 mg, 13%).

Workup

  1. custom—then partitioned between water and EtOAc
  2. washThe organic phase was washed with water
  3. dry with material—brine, —dried (sodium sulfate)
  4. customPurification by column chromatography
  5. washeluting with EtOAc in hexanes (10%-100%)—afforded the title compound as a yellow oil (26 mg, 13%)

Sources & evidence

ORD record
ord-c477bc0342384e3d814b47d07b71d2f8
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

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