Trifluoroacetic acid → 4-(1-Chloro-5-isoquinolyl)aminopiperidine trifluoroacetate

HRID 10543Notes

Reaction equation

HRID 10543 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([NH:12][CH:13]3[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29]>C(Cl)Cl>[F:26][C:27]([F:32])([F:31])[C:28]([OH:30])=[O:29].[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([NH:12][CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 219798294-(1-Chloro-5-isoquinolyl)amino-1-(tert-butoxycarbonyl)piperidine

Product 1

HCID 219798754-(1-Chloro-5-isoquinolyl)aminopiperidine trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Deprotection was performed (room temperature, 2 hours) by using Intermediate 84 (81.9 mg) and a mixed solution of trifluoroacetic acid and methylene chloride (1:1, 2 ml). The solvent was evaporated under reduced pressure, and the residue was added with methanol (2 ml) and diethyl ether (6 ml). The deposited precipitates were collected by filtration and washed with diethyl ether to obtain the title compound (64 mg) as yellow powdery crystals.

Workup

  1. custom(room temperature, 2 hours)
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue was added with methanol (2 ml) and diethyl ether (6 ml)
  4. customThe deposited precipitates
  5. filtrationwere collected by filtration
  6. washwashed with diethyl ether

Sources & evidence

ORD record
ord-c7ab94fd6f5a4dc4b97d834fc0e5f2b3
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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