Hydrochloric Acid → 2-{3-[2-(3,4-Dichlorophenyl)azetidin-1-yl]prop-1-ylamino}-1H-quinolin-4-one

HRID 430075노트

반응식

HRID 430075 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:12][CH2:11][N:10]2[CH2:13][CH2:14][CH2:15][NH:16][C:17]2[CH:26]=[C:25]([O:27]C)[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:12][CH2:11][N:10]2[CH2:13][CH2:14][CH2:15][NH:16][C:17]2[NH:18][C:19]3[C:24]([C:25](=[O:27])[CH:26]=2)=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

3

반응물 2

HCID 313Hydrochloric AcidHCID 18353676HCID 18353676, 화합물

생성물 1

HCID 183536702-{3-[2-(3,4-Dichlorophenyl)azetidin-1-yl]prop-1-ylamino}-1H-quinolin-4-one수율 23.3%

실험 절차

2-{3-[2-(3,4-Dichlorophenyl)azetidin-1-yl]prop-1-ylamino}-4-methoxyquinoline (0.04 g, 0.096 mmol) was treated at reflux with 10M HCl (4 ml) for 45 min. The reaction mixture was evaporated to dryness, and the residue purified by chromatography on silica gel eluting with 10% (9:1 MeOH/NH3) in dichloromethane to give the title compound as a colourless gum (9 mg, 23%); δH (CD3OD) 1.75 (2H, m), 2.2 (1H, m), 2.45 (1H, m), 2.7-2.9 (2H, m), 3.05 (1H, m), 3.35 (2H, m), 3.55 (1H, m), 5.7 (1H, s), 7.3-7.5 (4H, m), 7.6-7.7 (2H, m), 8.1 (1H, dd); MS (ES+) 402/404 (53/39%, MH+), 230 (60), 187 (100).

후처리

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue purified by chromatography on silica gel eluting with 10% (9:1 MeOH/NH3) in dichloromethane

출처 및 근거

ORD 기록
ord-8aa651ee50bd4d3782946a17f219a591
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06320051B1

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