Triethylamine → HCID 14882524, compound

HRID 330158Notes

Reaction equation

HRID 330158 reaction equation
[CH2:1]([NH:4][C:5](/[CH:7]=[CH:8]/[C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:18][C:19]2[CH:37]=[CH:36][C:22]([C:23]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])(=[O:28])=[O:27])=[O:24])=[CH:21][C:20]=2[O:38][CH3:39])=[CH:11][CH:10]=1)=[O:6])[CH2:2][CH3:3].C(N(CC)CC)C.[H][H]>[Pd].C(O)C>[CH2:1]([NH:4][C:5]([CH2:7][CH2:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][N:15]2[CH2:18][C:19]2[CH:37]=[CH:36][C:22]([C:23]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])(=[O:28])=[O:27])=[O:24])=[CH:21][C:20]=2[O:38][CH3:39])=[CH:11][CH:10]=1)=[O:6])[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 14882520HCID 14882520, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14882524HCID 14882524, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10% w/w, 0.01 g) was added to a solution of E-4-[6-[2-(propylcarbamoyl)vinyl]indol-1-ylmethyl]-3-methoxy-N-(2-methylphenylsulfonyl)benzamide (0.1 g) and triethylamine (0.026 ml) in ethanol (5 ml). The mixture was vigorously stirred and hydrogenated at atmospheric pressure. When hydrogen uptake had ceased, the catalyst was removed by filtration through diatomaceous earth, the filter pad washed with ethanol, the filtrate diluted with water (10 ml) and acidified to pH 4 with 1M hydrochloric acid. The ethanol was evaporated; and the white solid which precipitated from the aqueous residue was isolated by filtration, washed with water and dried to give the title compound (80 mg, 80%) as a white solid; mp 110°.

Workup

  1. customthe catalyst was removed by filtration through diatomaceous earth
  2. washthe filter pad washed with ethanol
  3. additionthe filtrate diluted with water (10 ml)
  4. customThe ethanol was evaporated
  5. customand the white solid which precipitated from the aqueous residue
  6. customwas isolated by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-52b948b3bdd2418bb583fa24a6319363
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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