HCID 86583627, compound → HCID 22467208, compound

HRID 381311Notes

Reaction equation

HRID 381311 reaction equation
[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:14]([C:34]3[CH:42]=[CH:41][C:37]4[O:38][CH2:39][O:40][C:36]=4[CH:35]=3)[C:15]([NH:17][S:18]([C:21]3[CH:26]=[CH:25][C:24](/[CH:27]=[CH:28]/[C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:23][CH:22]=3)(=[O:20])=[O:19])=[O:16])=[CH:9][N:10]2[CH3:13])=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[H][H]>C(O)C.[Pd]>[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([CH:14]([C:34]3[CH:42]=[CH:41][C:37]4[O:38][CH2:39][O:40][C:36]=4[CH:35]=3)[C:15]([NH:17][S:18]([C:21]3[CH:22]=[CH:23][C:24]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:25][CH:26]=3)(=[O:20])=[O:19])=[O:16])=[CH:9][N:10]2[CH3:13])=[CH:6][CH:5]=1)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 86583627HCID 86583627, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22467208HCID 22467208, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Ethyl (E)-3-(4-[2-(6-carbamoyl-1-methyl-1H-3-indolyl)-2-(1,3-benzodioxol-5-yl)acetyl] sulfamoylphenyl)-2-propenoate (the compound of Example 41, 0.24 g, 0.40 mmol) was dissolved in ethanol (5 ml) and 5% palladium-on-carbon (24 mg) was added. The mixture was placed in a pressure vessel and a hydrogen pressure of 345 kPa (50 psi) was maintained for 48 h. The reaction mixture was filtered through Arbocel™ and concentrated in vacuo. Flash column chromatography (elution with 5% methanol/90% dichloromethane) gave the product (70 mg).

Workup

  1. customThe mixture was placed in a pressure vessel
  2. filtrationThe reaction mixture was filtered through Arbocel™
  3. concentrationconcentrated in vacuo
  4. washFlash column chromatography (elution with 5% methanol/90% dichloromethane)

Sources & evidence

ORD record
ord-f3e1b4476bb44252a537ea0a008a12c3
Source dataset
uspto-grants-2001_10
Patent number
US06306852B1

Reaction notes

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