HCID 10476613, compound → HCID 10093160, compound

HRID 227486Notes

Reaction equation

HRID 227486 reaction equation
[N:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[C:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:17]=3)[NH:12][C:11]=2[C:27]([NH2:29])=[O:28])(=[O:9])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>CO>[N:1]1([S:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:17]=3)[NH:12][C:11]=2[C:27]([NH2:29])=[O:28])(=[O:8])=[O:9])[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

3

Reactant 1

HCID 10476613HCID 10476613, compound

Product 1

HCID 10093160HCID 10093160, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(Morpholin-4-ylsulfonyl)-5-(phenylethynyl)-1H-indole-2-carboxamide (50 mg, 0.12 mmol, 1.0 equiv) was dissolved in 10 mL of methanol. The vessel was degassed and charged with 10% palladium on carbon (5 mg, 10 weight percent). The vessel was then charged with 1 atm. H2 and stirred vigorously for 1 hour. The reaction was filtered through a pad of Celite, the pad was washed with methanol and the filtrate was concentrated in vacuo to provide the title compound. Proton NMR was consistent with the titled compound. HRMS (ES) exact mass calculated for C21H24N3O4S (M+H+): 414.1482. Found 414.1479.

Workup

  1. customThe vessel was degassed
  2. additioncharged with 10% palladium on carbon (5 mg, 10 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-35173586f388480d9d8dc4992fa7bab7
Source dataset
uspto-grants-2009_07
Patent number
US07560546B2

Reaction notes

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