Ethylene Glycol → HCID 68561617, compound

HRID 1517328Notes

Reaction equation

HRID 1517328 reaction equation
[OH-].[Na+].C(O)CO.N1(C([N:14]2[CH2:19][CH2:18][CH:17]([O:20][C:21]3[N:26]=[CH:25][N:24]=[C:23]([N:27]4[C:35]5[C:30](=[CH:31][C:32]([S:36]([CH2:39][CH2:40][CH3:41])(=[O:38])=[O:37])=[CH:33][CH:34]=5)[CH2:29][CH2:28]4)[CH:22]=3)[CH2:16][CH2:15]2)=O)C=CN=C1>O>[NH:14]1[CH2:15][CH2:16][CH:17]([O:20][C:21]2[N:26]=[CH:25][N:24]=[C:23]([N:27]3[C:35]4[C:30](=[CH:31][C:32]([S:36]([CH2:39][CH2:40][CH3:41])(=[O:38])=[O:37])=[CH:33][CH:34]=4)[CH2:29][CH2:28]3)[CH:22]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 14798Sodium HydroxideHCID 68563097HCID 68563097, compound

Product 1

HCID 68561617HCID 68561617, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 2 N aqueous sodium hydroxide solution (363 mL, 0.726 mmol) was added to an ethylene glycol (3.6 mL) solution of the 1-(6-{[1-(1H-imidazol-1-ylcarbonyl)piperidin-4-yl]oxy}pyrimidin-4-yl)-5-(propylsulfonyl)indoline (180 mg, 0.363 mmol) produced in Reference Example 33, and the mixture was stirred at 100° C. for 2.5 hours. To the reaction solution, water was added, followed by extraction with ethyl acetate three times. The obtained organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the title compound as white powder (106 mg, yield: 73%).

Workup

  1. customproduced in Reference Example 33
  2. extractionfollowed by extraction with ethyl acetate three times
  3. washThe obtained organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4a5a3131fcbd4961bf4214b652e5b498
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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