Trifluoroacetic acid → 1,1-Dimethylpropyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate

HRID 1517345Notes

Reaction equation

HRID 1517345 reaction equation
F[C:2](F)(F)C(O)=O.[CH3:8][S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[N:26]=[CH:25][N:24]=[C:23]([O:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]3)[CH:22]=1)[CH2:16][CH2:15]2)(=[O:11])=[O:10]>ClCCl>[CH3:2][C:28]1([OH:27])[CH2:29][CH2:30][CH2:32][CH2:33]1.[CH3:39][C:37]([OH:36])([CH2:40][CH3:2])[CH3:38].[CH3:8][S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[N:26]=[CH:25][N:24]=[C:23]([O:27][CH:28]3[CH2:29][CH2:30][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH2:38][CH3:2])=[O:35])[CH2:32][CH2:33]3)[CH:22]=1)[CH2:16][CH2:15]2)(=[O:11])=[O:10]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 25242414Tert-butyl 4-((6-(5-(methylsulfonyl)indolin-1-yl)pyrimidin-4-yl)oxy)piperidine-1-carboxylate

Product 3

HCID 64052-Methyl-2-butanolHCID 738301-MethylcyclopentanolHCID 685631211,1-Dimethylpropyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylateYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (2 mL) was added to a dichloromethane (10 mL) solution of the tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate (430 mg, 0.881 mmol) produced in Example 1, and the mixture was stirred at room temperature for 2 hours. From the reaction solution, the solvent was distilled off under reduced pressure. The same reaction as in the method described in Example 102 was performed using a portion (201 mg) of the obtained residue and, instead of 1-methylcyclopentanol, 2-methyl-2-butanol to obtain the title compound as white powder (50.4 mg, yield: 19%).

Workup

  1. distillationFrom the reaction solution, the solvent was distilled off under reduced pressure
  2. customThe same reaction as in the method

Sources & evidence

ORD record
ord-54ebcadfbc3e41b991e169930848bbb4
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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