Trifluoroacetic acid → HCID 59134441, compound

HRID 1993694Notes

Reaction equation

HRID 1993694 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:31][C:32]3[N:33]([C:41]4[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=4)[N:34]=[C:35]([C:37]([CH3:40])([CH3:39])[CH3:38])[CH:36]=3)=[O:30])=[C:24]([CH3:48])[N:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[C:37]([C:35]1[CH:36]=[C:32]([NH:31][C:29]([NH:28][C:25]2[C:24]([CH3:48])=[N:23][C:22]([O:21][CH:18]3[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)=[CH:27][CH:26]=2)=[O:30])[N:33]([C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][CH:42]=2)[N:34]=1)([CH3:40])([CH3:39])[CH3:38]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68540208HCID 68540208, compound

Product 1

HCID 59134441HCID 59134441, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

Add trifluoroacetic acid (10 mL) to a cold solution of 4-{5-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-6-methyl-pyridin-2-yloxy}-piperidine-1-carboxylic acid tert-butyl ester (746 mg, 1.33 mmol) in dichloromethane (20 mL). Stir the reaction mixture at 22° C. for 25 min. After removal of solvent, treat the residue with 1 N sodium hydroxide (20 mL) and extract three times with dichloromethane (20 mL each). Dry the combined organic phases over sodium sulfate. Removal of solvent provides a white solid (605 mg, 98% yield). MS(ES+): m/z=463.2 [M+H].

Workup

  1. customAfter removal of solvent
  2. additiontreat the residue with 1 N sodium hydroxide (20 mL)
  3. extractionextract three times with dichloromethane (20 mL each)
  4. dry with materialDry the combined organic phases over sodium sulfate
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-5bdff6aa00724eb9917c7445d85252dc
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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