Triethylamine → HCID 178488319, compound

HRID 1250399Notes

Reaction equation

HRID 1250399 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=3)[C:15]3[C:20]([CH:21]=2)=[C:19]([O:22][CH3:23])[CH:18]=[CH:17][CH:16]=3)=[O:12])=[CH:4][CH:3]=1.Cl.[NH2:34][OH:35].C(N(CC)CC)C>C(O)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31](=[NH:32])[NH:34][OH:35])[CH:26]=3)[C:15]3[C:20]([CH:21]=2)=[C:19]([O:22][CH3:23])[CH:18]=[CH:17][CH:16]=3)=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 10906011HCID 10906011, compound

Product 1

HCID 178488319HCID 178488319, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material 1-(3-cyano-benzyl)-4-methoxy-1H-indole-2-carboxylic acid 2-(4-hydroxyphenyl)ethyl amide (example 25/1) was dissolved in ethanol and hydroxylamine hydrochloride and triethylamine were added. After reflux for 5 h the reaction mixture was concentrated in vacuo and partitioned between dichloromethane and water. The organic layer was separated, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with dichloromethane/methanol 19:1 to give 63% of the desired product, which solidified under water. M.p. 173-175° C. (dec.). MS: 459.3 (M+H+).

Workup

  1. temperatureAfter reflux for 5 h the reaction mixture
  2. concentrationwas concentrated in vacuo
  3. custompartitioned between dichloromethane and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography on silica gel with dichloromethane/methanol 19:1

Sources & evidence

ORD record
ord-b867d3b66cb24262a9f67c0a4ac130e8
Source dataset
uspto-grants-2002_01
Patent number
US06337344B1

Reaction notes

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