Triethylamine → HCID 178479693, compound

HRID 278620

Reaction equation

HRID 278620 reaction equation
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([S:17]([C:20]3[CH:29]=[CH:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([Cl:30])[CH:26]=4)[CH:21]=3)(=[O:19])=[O:18])[CH2:13][CH2:12]2)=[O:10])[CH2:5][CH2:4]1.C(N(CC)CC)C.CS[C:40]1[NH:41][CH2:42][CH2:43][N:44]=1>C(O)C>[ClH:30].[Cl:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][CH:24]=1)[CH:21]=[C:20]([S:17]([N:14]1[CH2:13][CH2:12][N:11]([C:9]([C@H:6]3[CH2:7][CH2:8][C@H:3]([NH:2][N:44]4[CH2:43][CH2:42][N:41]=[CH:40]4)[CH2:4][CH2:5]3)=[O:10])[CH2:16][CH2:15]1)(=[O:18])=[O:19])[CH:29]=[CH:28]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 883692-Methylthio-2-imidazoline hydroiodideHCID 178479260HCID 178479260, compound

Product 1

HCID 178479693HCID 178479693, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-(trans-4-aminocyclohexane-1-ylcarbonyl)-4-(6-chloronaphthalene-2-sulfonyl)piperazine hydrochloride (100 mg) and triethylamine (120 mg) in ethanol (10 ml) was added 2-methylthioimidazoline (116 mg), and the mixture was heated for 48 hours under reflux. The reaction solution was concentrated, and the residue was purified with silica gel column chromatography (dichloromethane/methanol containing 10% ammonia=10/1) and transformed into hydrochloride with 4 N hydrochloric acid in ethyl acetate to give a colorless solid of the title compound (30 mg).

Workup

  1. temperaturethe mixture was heated for 48 hours
  2. temperatureunder reflux
  3. concentrationThe reaction solution was concentrated
  4. customthe residue was purified with silica gel column chromatography (dichloromethane/methanol containing 10% ammonia=10/1)

Sources & evidence

ORD record
ord-0b9c4a1b28694e43996b770efe9ae48b
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Linked notes

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