Trifluoroacetic acid → HCID 24697849, compound

HRID 75106Notes

Reaction equation

HRID 75106 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[CH:5][C:6]([NH:9][CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[N:7][CH:8]=1.FC(F)(F)C(O)=O>ClCCl>[NH:13]1[CH2:12][CH2:11][CH:10]([NH:9][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:23])([F:1])[F:24])=[CH:8][N:7]=2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58576452HCID 58576452, compound

Product 1

HCID 24697849HCID 24697849, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.860 g (2.49 mmol) of tert-butyl 4-(5-(trifluoromethyl)(pyridin-2-ylamino)piperidine-1-carboxylate obtained in stage 6.1. is dissolved in 8.5 ml of dichloromethane. 1.91 ml of trifluoroacetic acid are added and the mixture is stirred at ambient temperature for 4 hours. The dichloromethane is evaporated and then the residue is coevaporated twice with 10 ml of 1,2-dichloroethane. The residue is taken up in a mixture of 50 ml of ethyl acetate, 10 ml of a 1N aqueous sodium hydroxide solution and 5 ml of a 33% aqueous ammonia solution. The organic phase is separated by settling. It is washed with 2 times 10 ml of water and then with 10 ml of a saturated aqueous sodium chloride solution. It is dried over sodium sulphate and evaporated to dryness to produce 0.572 g (2.33 mmol) of product in the form of an off-white solid.

Workup

  1. customThe dichloromethane is evaporated
  2. additionThe residue is taken up in a mixture of 50 ml of ethyl acetate, 10 ml of a 1N aqueous sodium hydroxide solution and 5 ml of a 33% aqueous ammonia solution
  3. customThe organic phase is separated
  4. washIt is washed with 2 times 10 ml of water
  5. dry with materialIt is dried over sodium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-99172d101c6d48db8f262eca04c25702
Source dataset
uspto-grants-2014_09
Patent number
US08835418B2

Reaction notes

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