Hydrochloric Acid → 5-[3-(Ethylsulfonyl)phenyl]-3-methyl-9H-pyrido[2,3-b]indole-7-carboxamide

HRID 1882232Notes

Reaction equation

HRID 1882232 reaction equation
[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[C:17]3[C:13]=2[C:14]2[CH:26]=[C:25]([CH3:27])[CH:24]=[N:23][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2].[OH-:28].[K+].Cl>O1CCOCC1.OO>[CH2:1]([S:3]([C:6]1[CH:7]=[C:8]([C:12]2[CH:20]=[C:19]([C:21]([NH2:22])=[O:28])[CH:18]=[C:17]3[C:13]=2[C:14]2[CH:26]=[C:25]([CH3:27])[CH:24]=[N:23][C:15]=2[NH:16]3)[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 58880044HCID 58880044, compound

Product 1

HCID 250169945-[3-(Ethylsulfonyl)phenyl]-3-methyl-9H-pyrido[2,3-b]indole-7-carboxamideYield 47%

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 126 (30 mg, 0.08 mmol) stirred in dioxane (2 mL) at r.t. A solution of potassium hydroxide (25 mg, 0.44 mmol) in 30% H2O2 solution (1 mL) was added, and the reaction stirred for 18 h. The solution was neutralized with 1N HCl and concentrated in vacuo. Purification by silica gel chromatography (5 to 8% MeOH/CH2Cl2 gave 14.8 mg (47%) of the title compound as a white solid. 1H NMR (400 MHz, CD3OD) δ 8.28 (s, 1H), 8.22 (s, 1H), 8.12 (s, 1H), 8.10 (d, 1H, J=7.6 Hz), 8.02 (d, 1H, J=7.6 Hz), 7.88 (t, 1H, J=7.6 Hz), 7.68 (s, 1H), 7.62 (s, 1H), 3.34 (q, 2H, J=7.2 Hz), 2.31 (s, 3H), 1.29 (t, 3H, J=7.2 Hz). MS (ES) [m+H] calc'd for C21H19N3O3S, 394; found 394.

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by silica gel chromatography (5 to 8% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1fb6534ec1184674bdd70399e41fbad0
Source dataset
uspto-grants-2012_11
Patent number
US08318939B2

Reaction notes

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