Triethylamine → HCID 178488697, 화합물

HRID 644018노트

반응식

HRID 644018 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 178488697HCID 178488697, 화합물수율 33.8%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ab8ac4e2313e42b687019ae38bd5afd6
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07700634B2

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