HCID 57445040, compound → 7-Aminomethyl-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide

HRID 227508Notes

Reaction equation

HRID 227508 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH2:14])=[O:13])=[C:8]2[S:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)(=[O:17])=[O:16])#[N:2]>CO>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH2:14])=[O:13])=[C:8]2[S:15]([N:18]1[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1)(=[O:17])=[O:16]

Participants

3

Reactant 1

HCID 57445040HCID 57445040, compound

Product 1

HCID 577561277-Aminomethyl-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Cyano-3-(morpholin-4-ylsulfonyl)-1H-indole-2-carboxamide (8 mg, 0.024 mmol) was dissolved in 5 mL of methanol. The vessel was degassed and charged with 10% Pd(OH)2 on carbon (0.4 mg, 5 weight percent). The vessel was then charged with 1 atm. H2 and stirred vigorously for 18 hours. The reaction was filtered through a pad of Celite, the pad was washed with methanol and the filtrate was concentrated in vacuo. The title compound was obtained after purification by preparative reversed phase HPLC. Proton NMR for the product was consistent with the titled compound. ESI+MS: 339.3 [M+H]+.

Workup

  1. customThe vessel was degassed
  2. additioncharged with 10% Pd(OH)2 on carbon (0.4 mg, 5 weight percent)
  3. additionThe vessel was then charged with 1 atm
  4. filtrationThe reaction was filtered through a pad of Celite
  5. washthe pad was washed with methanol
  6. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d464f3220b2f43aba98a18a4919aa804
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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