3-(morpholin-4-ylsulfonyl)-7-nitro-1H-indole-2-carboxamide → 7-Amino-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide

HRID 227469Notes

Reaction equation

HRID 227469 reaction equation
[N:1]1([S:7]([C:10]2[C:18]3[C:13](=[C:14]([N+:19]([O-])=O)[CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[C:22]([NH2:24])=[O:23])(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H][H]>CO.[Pd]>[NH2:19][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[NH:12][C:11]([C:22]([NH2:24])=[O:23])=[C:10]2[S:7]([N:1]1[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1)(=[O:9])=[O:8]

Participants

5

Reactant 2

HCID 574450303-(morpholin-4-ylsulfonyl)-7-nitro-1H-indole-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 100191367-Amino-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-(morpholin-4-ylsulfonyl)-7-nitro-1H-indole-2-carboxamide (708 mg, 2.00 mmol) in 30 mL of methanol was added 10% palladium on carbon (200 mg), and the reaction was equipped with a balloon of hydrogen gas. After 2 hours, the reaction was filtered through celite, the filter pad was rinsed with ethyl acetate, and the resulting solution was concentrated in vacuo to provide the titled compound as a yellow solid. A portion of this was taken up in dichloromethane, treated with excess ethereal HCl, and concentrated in vacuo to give an off-white solid, used for biological testing. HRMS (ES) exact mass calculated for C13H17N4O4S (M+H+): 325.0965. Found 325.0971.

Workup

  1. filtrationthe reaction was filtered through celite
  2. washthe filter pad was rinsed with ethyl acetate
  3. concentrationthe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-436c2e68829d41f5a8c34f4018315490
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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