Trifluoroacetic acid → HCID 57832821, compound

HRID 729623Notes

Reaction equation

HRID 729623 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([NH:25][C:26]([NH:28][C:29]3[N:30]([C:38]4[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=4)[N:31]=[C:32]([C:34]([CH3:37])([CH3:36])[CH3:35])[CH:33]=3)=[O:27])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:34]([C:32]1[CH:33]=[C:29]([NH:28][C:26]([NH:25][C:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]([O:14][CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[N:16][CH:17]=2)=[O:27])[N:30]([C:38]2[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][CH:39]=2)[N:31]=1)([CH3:37])([CH3:35])[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69056157HCID 69056157, compound

Product 1

HCID 57832821HCID 57832821, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

To a cold solution of 4-{4-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-isoquinolin-1-yloxy}-piperidine-1-carboxylic acid tert-butyl ester (820 mg, 1.37 mmol) in dichloromethane (50 mL), add trifluoroacetic acid (15 mL). Stir the reaction mixture at 22° C. for 1.5 hours. After removal of solvent, treat the residue with 1N sodium hydroxide saturated with NaCl (50 mL) and extract five times with dichloromethane (50 mL each). Dry the combined organic phases over sodium sulfate. Filter the mixture and subject residue to silica gel chromatography eluting with dichloromethane and methanol to provide a white solid (515 mg, 75% yield, LCMS ES+ (m/z) 499.5 [M+H]).

Workup

  1. customAfter removal of solvent
  2. additiontreat the residue with 1N sodium hydroxide saturated with NaCl (50 mL)
  3. extractionextract five times with dichloromethane (50 mL each)
  4. dry with materialDry the combined organic phases over sodium sulfate
  5. filtrationFilter the mixture
  6. washeluting with dichloromethane and methanol
  7. customto provide a white solid (515 mg, 75% yield, LCMS ES+ (m/z) 499.5 [M+H])

Sources & evidence

ORD record
ord-259722e5a8b04e7f9be62e2e3aa9cf93
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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