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Butylamine → HCID 9901307, 화합물

HRID 1374756
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HRID 1374756 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][OH:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:14])[CH:3]=1.[CH2:15]([NH2:19])[CH2:16][CH2:17][CH3:18]>N1CCCC1>[CH2:15]([NH:19][C:12]([C:8]1[CH:7]=[C:6]2[C:11]([C:2]([N:19]3[CH2:18][CH2:17][CH2:16][CH2:15]3)=[CH:3][C:4]([CH3:14])=[N:5]2)=[CH:10][CH:9]=1)=[O:13])[CH2:16][CH2:17][CH3:18]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 8007ButylamineHCID 11264243HCID 11264243, 화합물

생성물 1

HCID 9901307HCID 9901307, 화합물수율 43%

시약·촉매·용매 1

HCID 31268Pyrrolidine용매

실험 절차

(4-Chloro-2-methyl-quinolin-7-yl)-methanol (example 2, 200 mg, 0.80 mmol) was refluxed in butylamine (2 mL) for 6 h. After cooling the reaction mixture was partitioned between sat. aq. ammonium chloride solution and dichloromethane. The organic layer was separated, dried (MgSO4), and evaporated. The residue was chromatographed (SiO2, CH2Cl2/MeOH 19:1) to produce a yellow oil, which was heated in pyrrolidine (2 mL) at 70° C. for 16 h. After cooling the reaction mixture was partitioned between sat. aq. ammonium chloride solution and dichloromethane. The organic layer was separated, dried (MgSO4), and evaporated. Chromatography (SiO2, dichloromethane/methanol 19:1) afforded the title compound (108 mg, 43%). White solid, ISP-MS: m/e=312.3 ([M+H]+).

후처리

  1. temperatureAfter cooling the reaction mixture
  2. customwas partitioned between sat. aq. ammonium chloride solution and dichloromethane
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed (SiO2, CH2Cl2/MeOH 19:1)
  7. customto produce a yellow oil, which
  8. temperatureAfter cooling the reaction mixture
  9. customwas partitioned between sat. aq. ammonium chloride solution and dichloromethane
  10. customThe organic layer was separated
  11. dry with materialdried (MgSO4)
  12. customevaporated

출처 및 근거

ORD 기록
ord-92e56e6ecf5e476eba07ac4d6bb6a8d7
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07166589B2

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