HCID 18612888, compound → HCID 18612725, compound

HRID 1420607Notes

Reaction equation

HRID 1420607 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[N:15]([C:23]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)=O)[CH2:14][CH:13]2[C:31](OC)=[O:32])(=[O:11])=[O:10])=[CH:5][CH:4]=1>O1CCCC1.CO>[OH:32][CH2:31][CH:13]1[N:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[CH2:18][C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=2[N:15]([CH2:23][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH2:14]1

Participants

4

Reactant 1

HCID 18612888HCID 18612888, compound

Product 1

HCID 18612725HCID 18612725, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.100 g (0.208 mmol) of methyl 4-(4-methoxybenzenesulfonyl)-1-(3-pyridinylcarbonyl)-2,3,4,5-tetrahydro-1H-[1,4]benzodiazepine-3-carboxylate and 3 ml of borane-tetrahydroforan complex in tetrahydrofuran (1.0 M) was refluxed overnight. The solution was cooled to room temperature, diluted with methanol and the solvent removed. Methanol was added several times and, after each addition. the solvent was removed. To the residue was added 1N NaHCO3. The mixture was stirred for 45 minutes and then extracted with ethyl acetate. The extract was concentrated and then washed with H2O, brine and dried with Na2SO4. The solvent was removed under vacuum and the residue chromatographed on thick layer silica gel plates with 10% methanol in ethyl acetate as solvent to give 60 mg of solid (RF 0.26). Crystallization from ethyl acetate gave 30 mg of white crystals. Anal. for C23H25N3O4S: Calc'd: C,62.8; H,5.7; N,9.6; S,7.3; Found: C,61.1; H,5.6; N,9.2; S,7.3; Mass spectrum (ES) 440.2 (M+H).

Workup

  1. temperaturewas refluxed overnight
  2. customthe solvent removed
  3. additionMethanol was added several times
  4. additionafter each addition
  5. customthe solvent was removed
  6. additionTo the residue was added 1N NaHCO3
  7. extractionextracted with ethyl acetate
  8. concentrationThe extract was concentrated
  9. washwashed with H2O, brine
  10. dry with materialdried with Na2SO4
  11. customThe solvent was removed under vacuum
  12. customthe residue chromatographed on thick layer silica gel plates with 10% methanol in ethyl acetate as solvent

Sources & evidence

ORD record
ord-1f0d170784674cab9cbf6a6b6804e736
Source dataset
uspto-grants-2000_06
Patent number
US06071903

Reaction notes

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