Tetrahydrofuran → 10,11-Dihydro-10-[[6-(cyclohexylthio)-3-pyridinyl]carbonyl]-5H-pyrrolo-[2,1-c][1,4]benzodiazepine

HRID 976415

Reaction equation

HRID 976415 reaction equation
[H-].[Na+].[CH:3]1([SH:9])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:10][N:11]1C(=O)N(C)CC[CH2:12]1.[CH:19]1[C:23]2=[CH:24][N:25]=[C:26]3[CH:32]=[CH:31][CH:30]=[CH:29][C:27]3=[CH:28][N:22]2[CH2:21][CH:20]=1.[O:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH:3]1([S:9][C:10]2[N:11]=[CH:12][C:36]([C:37]([N:25]3[C:26]4[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=4[CH2:28][N:22]4[CH:21]=[CH:20][CH:19]=[C:23]4[CH2:24]3)=[O:33])=[CH:35][CH:34]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 15290CyclohexanethiolHCID 24758Sodium hydrideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 66697609Pyrrolo[2,1-c][1,4]benzodiazepine

Product 1

HCID 1891747410,11-Dihydro-10-[[6-(cyclohexylthio)-3-pyridinyl]carbonyl]-5H-pyrrolo-[2,1-c][1,4]benzodiazepine

Procedure

To a suspension of 35 mg of sodium hydride (60% in oil) in 3 ml of tetrahydrofuran is added under argon 0.10 g of cyclohexylmercaptan. A white precipitate forms and after 0.5 hour at room temperature, 1 ml of N,N'-dimethylpropyleneurea is added. To the mixture is added 0.13 g of 10-[(6-chloro-3-pyridinyl)carbonyl]-10,11-dihydro-5[-pyrrolo[2,1-c][1,4]benzodiazepine in 2 ml of tetrahydrofuran. The mixture is stirred at room temperature for 18 hours, quenched with water and ammonium chloride and concentrated under vacuum. The aqueous suspension is filtered and the solid washed with water and hexane. The solid is purified by chromatography on silica gel prep-plates with ethyl acetate-hexane (1:4) as eluent to give 0.13 g of white solid; mass spectrum (CI): 404 (M+H).

Workup

  1. customquenched with water and ammonium chloride
  2. concentrationconcentrated under vacuum
  3. filtrationThe aqueous suspension is filtered
  4. washthe solid washed with water and hexane
  5. customThe solid is purified by chromatography on silica gel prep-plates with ethyl acetate-hexane (1:4) as eluent

Sources & evidence

ORD record
ord-f4f2777d106a43c78e05becf58c6202a
Source dataset
uspto-grants-1997_03
Patent number
US05612334

Linked notes

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