1,1'-Carbonyldiimidazole → HCID 21196159, compound

HRID 1066803Notes

Reaction equation

HRID 1066803 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:22])[C:10]3[C:15]([C:16]=2[CH2:17][CH2:18][C:19](O)=[O:20])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1.[C:25]([N:32]1[CH:36]=[CH:35]N=[CH:33]1)(N1C=CN=C1)=O.CN([N:40]1[CH2:45]CC[CH2:42][CH2:41]1)C>O1CCCC1>[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:22])[C:10]3[C:15]([C:16]=2[CH2:17][CH2:18][C:19]([N:40]2[CH2:45][CH2:35][CH:36]([N:32]([CH3:25])[CH3:33])[CH2:42][CH2:41]2)=[O:20])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 1426901-Piperidinamine, N,N-dimethyl-HCID 21196068HCID 21196068, compound

Product 1

HCID 21196159HCID 21196159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere 3-{2-[(4-chlorophenoxy)methyl]-1-methyl-1H-indol-3-yl}propanoic acid (0.286 g, 0.832 mmol) was dissolved in 6 ml of dry tetrahydrofuran. To this solution 1,1′-carbonyldiimidazole (0.141 g, 0.874 mmol) was added and the resulting mixture was stirred at room temperature for about two hours. The progress of the reaction was monitored by thin layer chromatography. The reaction mixture was then heated to 65° C. and maintained at this temperature for about 35 minutes. To this reaction mixture dimethylaminopiperidine (0.112 g, 0.874 mmol), dissolved in about 3.6 ml of tetrahydrofuran. This mixture was stirred at room temperature overnight.

Workup

  1. temperatureThe reaction mixture was then heated to 65° C.
  2. temperaturemaintained at this temperature for about 35 minutes
  3. stirringThis mixture was stirred at room temperature overnight

Sources & evidence

ORD record
ord-fb602e1baffa4adc900020459a877f79
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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