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

HRID 1517324Notes

Reaction equation

HRID 1517324 reaction equation
[ClH:1].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>[ClH:1].[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 685639645-(Methylsulfonyl)-1-[6-(piperidin-4-yloxy)pyrimidin-4-yl]indoline hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 4 N hydrochloric acid-ethyl acetate solution (20 mL) was added to an ethyl acetate (10 mL) suspension of tert-butyl 4-({6-[5-(methylsulfonyl)indolin-1-yl]pyrimidin-4-yl}oxy)piperidine-1-carboxylate (1.04 g, 2.19 mmol) produced in Example 1 below, and the mixture was stirred at room temperature for 1 hour. The reaction solution was filtered, and the obtained crude product was washed with ethyl acetate to obtain the title compound as white powder (898 mg, yield: equivalent).

Workup

  1. filtrationThe reaction solution was filtered
  2. customthe obtained crude product
  3. washwas washed with ethyl acetate

Sources & evidence

ORD record
ord-2b5740e6827145aaa706320b04b9960f
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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