HCID 22179371, compound → HCID 9840312, compound

HRID 992254Notes

Reaction equation

HRID 992254 reaction equation
C([N:8]1[CH2:21][CH2:20][C:19]2[C:18]3[CH:17]=[C:16]([S:22]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:24])=[O:23])[CH:15]=[CH:14][C:13]=3[NH:12][C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[C:25]1([S:22]([C:16]2[CH:15]=[CH:14][C:13]3[NH:12][C:11]4[CH2:10][CH2:9][NH:8][CH2:21][CH2:20][C:19]=4[C:18]=3[CH:17]=2)(=[O:24])=[O:23])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 22179371HCID 22179371, compound

Product 1

HCID 9840312HCID 9840312, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-benzyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (VIII, Step II, 453 mg, 1.09 mmol) in methanol (50 mL) is treated with palladium hydroxide (118 mg) and hydrogenated at 30 psi for 5 days. The mixture is filtered, rinsing with methanol and methylene chloride, and the filtrate concentrated under reduced pressure to give an amorphous solid. The material is purified by flash chromatography (Biotage 40M; methanol/methylene chloride, 5/95; methanol/methylene chloride/ammonium hydroxide, 20/79/1) to give the title compound. Analytical data for the hydrochloride salt, mp=290-291.5°; IR (drift) 3382, 2751, 2698, 2689, 2646, 2438, 1297, 1150, 1131, 1095, 801, 759, 722, 684 and 616 cm−1; NMR (300 MHz, DMSO-d6) 11.65, 7.35, 8.05-8.15, 7.85-7.95, 7.40-7.65, 3.20-3.40 and 3.10-3.25 δ; MS (EI) m/z 326 (M+), 298, 297, 286, 285, 284, 143 and 77; HRMS (FAB) calculated for C18H19N2O2S=327.1167, found 327.1165.

Workup

  1. filtrationThe mixture is filtered
  2. washrinsing with methanol and methylene chloride
  3. concentrationthe filtrate concentrated under reduced pressure
  4. customto give an amorphous solid
  5. customThe material is purified by flash chromatography (Biotage 40M; methanol/methylene chloride, 5/95; methanol/methylene chloride/ammonium hydroxide, 20/79/1)

Sources & evidence

ORD record
ord-dd1b871f941549b6922687255fc37c2e
Source dataset
uspto-grants-2002_10
Patent number
US06468999B1

Reaction notes

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