Dichloromethane → HCID 68560613, compound

HRID 1517334Notes

Reaction equation

HRID 1517334 reaction equation
C(N(C(C)C)CC)(C)C.Cl[C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12].ClCCl.[CH3:21][S:22]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34]1[CH:39]=[C:38]([O:40][CH:41]3[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]3)[N:37]=[CH:36][N:35]=1)[CH2:29][CH2:28]2)(=[O:24])=[O:23]>O>[CH3:21][S:22]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([C:34]1[N:35]=[CH:36][N:37]=[C:38]([O:40][CH:41]3[CH2:46][CH2:45][N:44]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[CH2:43][CH2:42]3)[CH:39]=1)[CH2:29][CH2:28]2)(=[O:24])=[O:23]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 61140Butyl chloroformateHCID 81531DiisopropylethylamineHCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

Product 1

HCID 68560613HCID 68560613, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Diisopropylethylamine (186 μL, 1.07 mmol) and butyl chloroformate (51 μL, 0.40 mmol) were added at 0° C. to a dichloromethane (5 mL) solution of the 5-(methylsulfonyl)-1-[6-(piperidin-4-yloxy)pyrimidin-4-yl]indoline (100 mg, 0.267 mmol) produced in Reference Example 28, and the mixture was stirred at room temperature for 1 hour. To the reaction solution, water was added, followed by extraction with ethyl acetate three times. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-1:2, V/V) to obtain the title compound as white powder (53.9 mg, yield: 43%).

Workup

  1. customproduced in Reference Example 28
  2. extractionfollowed by extraction with ethyl acetate three times
  3. washThe obtained organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1-1:2, V/V)

Sources & evidence

ORD record
ord-7af1099dd3344c1d9f9ad543482cb904
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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