Triethylamine → HCID 68563097, compound

HRID 1517327Notes

Reaction equation

HRID 1517327 reaction equation
C(N(CC)CC)C.[C:8]([N:15]1[CH:19]=[CH:18][N:17]=[CH:16]1)([N:10]1[CH:14]=[CH:13]N=[CH:11]1)=[O:9].Cl.N1CC[CH:24]([O:27][C:28]2[N:33]=[CH:32][N:31]=[C:30]([N:34]3[C:42]4[C:37](=[CH:38][C:39]([S:43]([CH2:46][CH2:47][CH3:48])(=[O:45])=[O:44])=[CH:40][CH:41]=4)[CH2:36][CH2:35]3)[CH:29]=2)[CH2:23]C1>C1COCC1>[N:15]1([C:8]([N:10]2[CH2:11][CH2:23][CH:24]([O:27][C:28]3[N:33]=[CH:32][N:31]=[C:30]([N:34]4[C:42]5[C:37](=[CH:38][C:39]([S:43]([CH2:46][CH2:47][CH3:48])(=[O:45])=[O:44])=[CH:40][CH:41]=5)[CH2:36][CH2:35]4)[CH:29]=3)[CH2:13][CH2:14]2)=[O:9])[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 68562847HCID 68562847, compound

Product 1

HCID 68563097HCID 68563097, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (286 μL, 2.05 mmol) and 1,1′-carbonyldiimidazole (249 mg, 1.54 mmol) were added to a THF (9.00 mL) solution of the 1-[6-(piperidin-4-yloxy)pyrimidin-4-yl]-5-(propylsulfonyl)indoline hydrochloride (450 mg, 1.03 mmol) produced in Reference Example 32, and the mixture was stirred at room temperature for 3 hours. 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 (291 mg, yield: 57%).

Workup

  1. customproduced in Reference Example 32
  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-6fbb86e4a1024602aebc285d74934058
Source dataset
uspto-grants-2012_07
Patent number
US08232287B2

Reaction notes

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