Hydrogen chloride-ethyl acetate → 5-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

HRID 1517325Notes

Reaction equation

HRID 1517325 reaction equation
Cl.C(OCC)(=O)C.[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(OC(C)(C)C)=O)[CH2:30][CH2:29]3)[CH:22]=1)[CH2:16][CH2:15]2)(=[O:11])=[O:10]>C(OCC)(=O)C>[CH3:8][S:9]([C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[N:17]([C:21]1[CH:22]=[C:23]([O:27][CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[N:24]=[CH:25][N:26]=1)[CH2:16][CH2:15]2)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 25242414Tert-butyl 4-((6-(5-(methylsulfonyl)indolin-1-yl)pyrimidin-4-yl)oxy)piperidine-1-carboxylate

Product 1

HCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indolineYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 4 N hydrochloric acid-ethyl acetate solution (9.45 mL) was added at 0° C. to an ethyl acetate (3.15 mL) suspension of tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate (630 mg, 1.33 mmol) produced in Example 1 below, and the mixture was stirred for 1 hour. The solvent was distilled off under reduced pressure. To the obtained residue, a 1 N aqueous sodium hydroxide solution (20 mL) was added, and the deposit was collected by filtration and washed with water to obtain the title compound as white powder (489 mg, yield: 99%).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. additionTo the obtained residue, a 1 N aqueous sodium hydroxide solution (20 mL) was added
  3. filtrationthe deposit was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-23a288d727d74915b0c5bc8be1fe90dc
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

Loading…