HCID 66850494, compound → HCID 66850828, compound

HRID 1515473Notes

Reaction equation

HRID 1515473 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-fcb6cfe6dc4a417bb9dbd150d6843f44
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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