1,1'-Carbonyldiimidazole → HCID 68561483, compound

HRID 1517326Notes

Reaction equation

HRID 1517326 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)([N:3]1[CH:7]=[CH:6]N=[CH:4]1)=[O:2].[CH3:13][S:14]([C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]1[CH:31]=[C:30]([O:32][CH:33]3CCNC[CH2:34]3)[N:29]=[CH:28][N:27]=1)[CH2:21][CH2:20]2)(=[O:16])=[O:15]>C1COCC1>[N:8]1([C:1]([N:3]2[CH2:4][CH2:34][CH:33]([O:32][C:30]3[N:29]=[CH:28][N:27]=[C:26]([N:22]4[C:23]5[C:19](=[CH:18][C:17]([S:14]([CH3:13])(=[O:16])=[O:15])=[CH:25][CH:24]=5)[CH2:20][CH2:21]4)[CH:31]=3)[CH2:6][CH2:7]2)=[O:2])[CH:12]=[CH:11][N:10]=[CH:9]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 667096685-(Methylsulfonyl)-1-(6-(piperidin-4-yloxy)pyrimidin-4-yl)indoline

Product 1

HCID 68561483HCID 68561483, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-carbonyldiimidazole (67.0 mg, 0.413 mmol) was added to a THF (2.06 mL) solution of the 5-(methylsulfonyl)-1-[6-(piperidin-4-yloxy)pyrimidin-4-yl]indoline (103 mg, 0.275 mmol) produced in Reference Example 28, and the mixture was stirred at room temperature for 1 hour. From the reaction solution, the solvent was distilled off under reduced pressure. To the residue, water was added, and the mixture was stirred. The deposit was collected by filtration and washed with water to obtain the title compound as white powder (105 mg, yield: 82%).

Workup

  1. customproduced in Reference Example 28
  2. distillationFrom the reaction solution, the solvent was distilled off under reduced pressure
  3. additionTo the residue, water was added
  4. stirringthe mixture was stirred
  5. filtrationThe deposit was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-a977f20a1ffd4595bc3492b77f19c760
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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