HCID 66850494, compound → HCID 66850828, compound

HRID 873673Notes

Reaction equation

HRID 873673 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([C:19]([C:21]4[CH:22]=[CH:23][C:24]([Cl:30])=[C:25]([S:27]([NH2:29])=[O:28])[CH:26]=4)=[O:20])=[CH:16][CH:17]=3)[C:12]3[CH2:31][CH2:32][N:33]([C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:34][C:11]2=3)(=O)=O)C=CC=CC=1>CO.[OH-].[Na+]>[Cl:30][C:24]1[CH:23]=[CH:22][C:21]([C:19]([C:15]2[CH:14]=[C:13]3[C:18](=[CH:17][CH:16]=2)[NH:10][C:11]2[CH2:34][N:33]([C:35](=[O:40])[C:36]([CH3:37])([CH3:38])[CH3:39])[CH2:32][CH2:31][C:12]3=2)=[O:20])=[CH:26][C:25]=1[S:27]([NH2:29])=[O:28]

Participants

4

Reactant 1

HCID 66850494HCID 66850494, compound

Product 1

HCID 66850828HCID 66850828, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-[9-Benzenesulfonyl-2-(2,2-dimethyl-propionyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-6-carbonyl]-2-chloro-benzenesulfinamide and its isomer (0.12 g, 0.195 mmol) are dissolved in 3 mL of 2:1 (v:v) mixture of methanol and 5 N aqueous sodium hydroxide then heated at reflux for 20 minutes. The reaction mixture is allowed to cool to room temperature and the methanol is removed in vacuo. The aqueous solution is acidified with 5 N HCl to pH 3 and then thoroughly extracted with ethyl acetate, the combined organic extracts are washed with water then a saturated sodium chloride solution, dried with magnesium sulfate, and concentrated in vacuo. Purification via preparative HPLC provides 0.014 g (15%) of the title compound as a yellow solid. 1H NMR (DMSO): δ 11.40 (s, 1H), 8.30 (s, 1H), 7.90 (m, 2H), 7.80 (m, 3H), 7.50-7.60 (m, 2H), 4.74 (s, 2H), 4.00 (m, 2H), 2.80 (m, 2H). MS (m/z): 472.1 (M−1).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 20 minutes
  3. customthe methanol is removed in vacuo
  4. extractionthoroughly extracted with ethyl acetate
  5. washthe combined organic extracts are washed with water
  6. dry with materiala saturated sodium chloride solution, dried with magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification via preparative HPLC

Sources & evidence

ORD record
ord-ec8198e19254483787869b33087a3afd
Source dataset
uspto-grants-2015_03
Patent number
US08975439B2

Reaction notes

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