Dichloromethane → HCID 68564660, compound

HRID 1517343Notes

Reaction equation

HRID 1517343 reaction equation
[CH:1]([N:4]=[C:5]=[O:6])([CH3:3])[CH3:2].ClCCl.[CH3:10][S:11]([C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([C:23]1[CH:28]=[C:27]([O:29][CH:30]3[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[N:26]=[CH:25][N:24]=1)[CH2:18][CH2:17]2)(=[O:13])=[O:12]>O>[CH:1]([NH:4][C:5]([N:33]1[CH2:32][CH2:31][CH:30]([O:29][C:27]2[CH:28]=[C:23]([N:19]3[C:20]4[C:16](=[CH:15][C:14]([S:11]([CH3:10])(=[O:13])=[O:12])=[CH:22][CH:21]=4)[CH2:17][CH2:18]3)[N:24]=[CH:25][N:26]=2)[CH2:35][CH2:34]1)=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 61277Isopropyl isocyanateHCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

Product 1

HCID 68564660HCID 68564660, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isopropyl isocyanate (31 μL, 0.315 mmol) was added to a dichloromethane (5 mL) solution of the 5-(methylsulfonyl)-1-[6-(piperidin-4-yloxy)pyrimidin-4-yl]indoline (78.1 mg, 0.209 mmol) produced in Reference Example 28, and the mixture was stirred at room temperature for 30 minutes. To the reaction solution, water was added, followed by extraction with ethyl acetate three times. The obtained organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate) to obtain the title compound as white powder (87.3 mg, yield: 91%).

Workup

  1. customproduced in Reference Example 28
  2. extractionfollowed by extraction with ethyl acetate three times
  3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-413abcdc7cd84a659c0c9df80864c996
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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