HCID 22179368, compound → HCID 9950493, compound

HRID 897157Notes

Reaction equation

HRID 897157 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[N:12]([CH2:31][CH3:32])[C:11]=2[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[CH2:31]([N:12]1[C:13]2[CH:14]=[CH:15][C:16]([S:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)(=[O:24])=[O:23])=[CH:17][C:18]=2[C:19]2[CH2:20][CH2:21][NH:8][CH2:9][CH2:10][C:11]1=2)[CH3:32]

Participants

4

Reactant 1

HCID 22179368HCID 22179368, compound

Product 1

HCID 9950493HCID 9950493, compound

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 23938PalladiumCatalyst

Procedure

A mixture of 3-benzyl-6-ethyl-9-(phenylsulfonyl)-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (Step I, 107 mg, 0.241 mmol) in methanol (20 mL, 1 drop concentrated hydrochloric acid) is treated with palladium on carbon (10%, 32 mg) and hydrogenated at 25 psi for 48 hr. The resulting mixture is filtered, rinsing with methanol and methylene chloride, and the filtrate is concentrated to a solid. The solid is purified via chromatography (10 g SG; methanol/methylene chloride/ammonium hydroxide, 20/79/1) to give the title compound, mp=224°, dec.; IR (drift) 2982, 2935, 2743, 1473, 1449, 1312. 1300, 1151, 1091, 819, 768, 728, 691, 647 and 623 cm−1; NMR (300 MHz, DMSO-d6) 8.09, 7.85-7.95, 7.45-7.65, 4.20, 2.95-3.25 and 1.15 δ; MS (EI) m/z 354 (M+), 312, 170, 167, 153, 143, 114, 78, 76 and 51; HRMS (FAB) calculated for C20H23N2O2S=355.1480, found 355.1488.

Workup

  1. filtrationThe resulting mixture is filtered
  2. washrinsing with methanol and methylene chloride
  3. concentrationthe filtrate is concentrated to a solid
  4. customThe solid is purified via chromatography (10 g SG; methanol/methylene chloride/ammonium hydroxide, 20/79/1)

Sources & evidence

ORD record
ord-3aa11b71d28645f5bcd0748b219985c6
Source dataset
uspto-grants-2005_07
Patent number
US06921823B2

Reaction notes

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