1,1'-Carbonyldiimidazole → HCID 24756896, compound

HRID 1820371Notes

Reaction equation

HRID 1820371 reaction equation
[N:1]1([C:7]([C:9]2[N:10]([CH2:21][C:22]([F:25])([F:24])[F:23])[C:11]3[C:16]([CH:17]=2)=[CH:15][C:14]([C:18]([OH:20])=O)=[CH:13][CH:12]=3)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH:38]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1)([CH3:40])[CH3:39]>O1CCCC1>[CH:38]([N:41]1[CH2:46][CH2:45][N:44]([C:18]([C:14]2[CH:15]=[C:16]3[C:11](=[CH:12][CH:13]=2)[N:10]([CH2:21][C:22]([F:23])([F:25])[F:24])[C:9]([C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:8])=[CH:17]3)=[O:20])[CH2:43][CH2:42]1)([CH3:40])[CH3:39]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 780131-IsopropylpiperazineHCID 686815812-(Morpholine-4-carbonyl)-1-(2,2,2-trifluoro-ethyl)-1H-indole-5-carboxylic acid

Product 1

HCID 24756896HCID 24756896, compoundYield 68.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(morpholine-4-carbonyl)-1-(2,2,2-trifluoro-ethyl)-1H-indole-5-carboxylic acid (100 mg, 0.28 mmol) and 1,1′-carbonyl-diimidazole (59 mg, 0.37 mmol) in tetrahydrofuran was stirred at room temperature overnight. 1-Isopropylpiperazine (72 mg, 0.56 mmol) was then added and the mixture was stirred for an additional 40 min. The volatiles were removed in vacuo and the residue was purified by flash chromatography on silica gel with dichloromethane:methanol:ammonia (95:5:0.25 v/v) as eluant, to give 90 mg (68%) of the desired compound as an off-white solid.

Workup

  1. stirringthe mixture was stirred for an additional 40 min
  2. customThe volatiles were removed in vacuo
  3. customthe residue was purified by flash chromatography on silica gel with dichloromethane:methanol:ammonia (95:5:0.25 v/v) as eluant

Sources & evidence

ORD record
ord-8e65cdb8b0fe46e887b7efbf39ecbfd2
Source dataset
uspto-grants-2009_10
Patent number
US07601711B2

Reaction notes

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