Trifluoroacetic acid → HCID 89586276, compound

HRID 1747831Notes

Reaction equation

HRID 1747831 reaction equation
[C:1]([CH2:3][N:4]([C:12]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:15]=[CH:14][CH:13]=1)C(=O)OC(C)(C)C)#[N:2].C(O)(C(F)(F)F)=O>ClCCl>[C:17]1([N:16]2[C:12]([NH:4][CH2:3][C:1]#[N:2])=[CH:13][CH:14]=[N:15]2)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 123151891HCID 123151891, compound

Product 1

HCID 89586276HCID 89586276, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (cyanomethyl)(1-phenyl-1H-pyrazol-5-yl)carbamate (4.38 g) in dichloromethane was added TFA (16.7 g) at room temperature, and the mixture was stirred for 5 hr. The reaction mixture was concentrated under reduced pressure, and adjusted to pH 9-10 with 1N aqueous sodium hydroxide solution. The reaction mixture was extracted with dichloromethane. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (1.90 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol)

Sources & evidence

ORD record
ord-9b97cdfa2f034327b68ab982e50d0187
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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