Hydrochloric Acid → 3-(aminomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

HRID 1822067노트

반응식

HRID 1822067 반응식
[N:1]([CH2:4][C:5]1[C:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([NH:17][C@H:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:19][CH3:20])=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N+]=[N-].Cl>C(O)C.[Pd]>[NH2:1][CH2:4][C:5]1[C:6]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[N:7][C:8]2[C:13]([C:14]=1[C:15]([NH:17][C@H:18]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:19][CH3:20])=[O:16])=[CH:12][CH:11]=[CH:10][CH:9]=2

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 578935703-(azidomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

생성물 1

HCID 578935693-(aminomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide수율 100.3%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A solution of 3-(azidomethyl)-2-phenyl-N-[(1s)-1-phenylpropyl]quinoline-4-carboxamide (2d) (1000 mg, 2.37 mmol) in ethanol (200 mL) were added Pd/C (10%, 1190 mg) and HCl (2N, 2.5 mL) was added. The reaction mixture were hydrogenated under 50 psi H2 at RT for 1.5 h. The catalyst was removed by filtration through a thick layer of diatomaceous earth, the filter was washed with ethanol and the washes and the ethanol solvent was combined and concentrated in vacuo. Crystallization from dichloromethane and ether afforded the title compound (940 mg, 92%) as a hydrogen chloride salt. 1H NMR (300 MHz, CDCl3) δ 0.92 (t, 3H), 2.01 (m, 2H), 3.18 (b, 3H), 4.39 (t, 2H), 5.16 (q, 1H), 7.30 (d, 2H), 7.34 (d, 2H), 7.39 (m, 1H), 7.78 (m, 2H), 7.84 (m, 2H), 8.08 (m, 1H), 8.30 (m, 2H), 8.44 (m, 2H). MS APCI, m/z=396 (M+1). LCMS: 1.70 min.

후처리

  1. additionwas added
  2. customThe catalyst was removed by filtration through a thick layer of diatomaceous earth
  3. washthe filter was washed with ethanol
  4. concentrationconcentrated in vacuo
  5. customCrystallization from dichloromethane and ether

출처 및 근거

ORD 기록
ord-16887ed28de44af09520f51d31754bed
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608628B2

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