Triethylamine → Diisopropyl Ether

HRID 1766200Notes

Reaction equation

HRID 1766200 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:10][C:11]1[CH:40]=[CH:39][C:14]2[N:15]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][CH2:27][C:28]([C:30]4[CH:35]=[C:34]([Br:36])[C:33]([NH2:37])=[C:32]([Br:38])[CH:31]=4)=[O:29])[CH2:21][CH2:20]3)[C:16](=[O:18])[NH:17][C:13]=2[CH:12]=1.C(N(CC)CC)C>C1COCC1>[NH2:37][C:33]1[C:34]([Br:36])=[CH:35][C:30]([C:28](=[O:29])[CH2:27][CH2:26][CH2:25][N:22]2[CH2:21][CH2:20][CH:19]([N:15]3[C:14]4[CH:39]=[CH:40][C:11]([NH:10][C:7]([CH:1]5[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]5)=[O:8])=[CH:12][C:13]=4[NH:17][C:16]3=[O:18])[CH2:24][CH2:23]2)=[CH:31][C:32]=1[Br:38].[CH:1]([O:29][CH:28]([CH3:27])[CH3:30])([CH3:6])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 211098785-amino-1-{1-[4-(4-amino-3,5-dibromophenyl)-4-oxobutyl]-4-piperidinyl}-1,3-dihydro-2(2H)-benzimidazolone

Product 2

HCID 7914Diisopropyl EtherHCID 211097741-{1-[4-(4-amino-3,5-dibromophenyl)-4-oxobutyl]-4-piperidinyl}-5-cyclohexanecarbonylamino-1,3-dihydro-2(2H)-benzimidazolone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

58.64 mg (0.40 mmol) of cyclohexanecarboxylic acid chloride were added to a solution of 200 mg (0.363 mmol) of 5-amino-1-{1-[4-(4-amino-3,5-dibromophenyl)-4-oxobutyl]-4-piperidinyl}-1,3-dihydro-2(2H)-benzimidazolone and 0.056 ml (0.40 mmol) of triethylamine in 10 ml of THF at a reaction temperature of 0° C. and the suspension formed was then stirred for 2 hours at ambient temperature. The mixture was evaporated down in vacuo, the residue was purified by column chromatography on silica gel (30–60 μm) using dichloromethane/methanol/cyclohexane/conc. ammonia 400/40/40/2.5 v/v/v/v as eluant. By working up the appropriate fractions. 106 mg (44% of theoretical) of the desired compound were obtained in the form of colourless crystals (diisopropyl-ether), Rf 0.67 (El B). IR (KBr): 1695.3 (C═O) MS: (M-H2O)+=641/643/645 (Br2)

Workup

  1. customthe suspension formed
  2. customThe mixture was evaporated down in vacuo
  3. customthe residue was purified by column chromatography on silica gel (30–60 μm)

Sources & evidence

ORD record
ord-0c5daf366b3f48a78be07509f3ac62b3
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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