Acetonitrile → (R)-3-(7-chloro-4-((2,2,2-trifluoroethylamino)methyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

HRID 132445Notes

Reaction equation

HRID 132445 reaction equation
[C:1]([O:9][C@H:10]([CH2:15][C:16]1[C:17]([CH2:26]Cl)=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[NH:21][N:20]=[CH:19]2)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(#N)C.[F:31][C:32]([F:36])([F:35])[CH2:33][NH2:34].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:9][C@H:10]([CH2:15][C:16]1[C:17]([CH2:26][NH:34][CH2:33][C:32]([F:36])([F:35])[F:31])=[C:18]2[C:22](=[C:23]([Cl:25])[CH:24]=1)[NH:21][N:20]=[CH:19]2)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 11430Potassium CarbonateHCID 59732079(R)-3-(7-chloro-4-(chloromethyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

Product 1

HCID 59732084(R)-3-(7-chloro-4-((2,2,2-trifluoroethylamino)methyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(R)-3-(7-chloro-4-(chloromethyl)-1H-indazol-5-yl)-1-methoxy-1-oxopropan-2-yl benzoate (6.80 g, 16.7 mmol) in acetonitrile (70.0 ml, 1340 mmol) was added 2,2,2-trifluoroethylamine (8.27 g, 84 mmol). After 20 min, potassium carbonate (2.308 g, 16.70 mmol) was added and the reaction mixture was refluxed for 2 h. The solvent was evaporated and the crude product was dissolved in a mixture of dichloromethane and chloroform. A thick emulsion formed and addition of methanol provided a clear organic phase. The organic layer was dried (Na2SO4), the solvent was removed and the crude product was used as such for the next step. MS (ESI) 470 (M+H); Rf=1.56.

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  2. customThe solvent was evaporated
  3. dissolutionthe crude product was dissolved in a mixture of dichloromethane and chloroform
  4. customA thick emulsion formed
  5. customprovided a clear organic phase
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. customthe solvent was removed

Sources & evidence

ORD record
ord-b0018a94c0ef46599cbee26c901b1357
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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