Triethylamine → HCID 178488697, compound

HRID 644018Notes

Reaction equation

HRID 644018 reaction equation
Cl.[NH2:2][OH:3].[CH:4]1([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][CH3:21])[C:13]([C:22]#[N:23])=[CH:12]2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C(N(CC)CC)C>C(O)C>[CH:4]1([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][C:18]=3[O:20][CH3:21])[C:13]([C:22]([NH:2][OH:3])=[NH:23])=[CH:12]2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 686987431-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbonitrile

Product 1

HCID 178488697HCID 178488697, compoundYield 33.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (966 mg, 13.9 mmol) was added to a mixture of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbonitrile (2.48 g, 9.24 mmol), triethylamine (1.41 g, 13.9 mmol), and ethanol (50 ml), then the resulting mixture was stirred at reflux for 20 h. After being cooled to room temperature, the reaction mixture was concentrated in vacuo. The obtained residue was mixed with water (150 ml), adjusted to pH 10 by the addition of aqueous sodium hydroxide and extracted with dichloromethane (4×100 ml). The organic layers were combined, washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The obtained residue was purified by column chromatography eluting with 10% (v/v) acetone in dichloromethane to give 1-(cyclohexyl)methyl-N-hydroxy-7-methoxy-1H-indole-3-carboxamidine (940 mg).

Workup

  1. temperatureat reflux for 20 h
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionThe obtained residue was mixed with water (150 ml)
  4. additionadjusted to pH 10 by the addition of aqueous sodium hydroxide
  5. extractionextracted with dichloromethane (4×100 ml)
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe obtained residue was purified by column chromatography
  10. washeluting with 10% (v/v) acetone in dichloromethane

Sources & evidence

ORD record
ord-ab8ac4e2313e42b687019ae38bd5afd6
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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