Triethylamine → HCID 178471809, 화합물

HRID 1961623노트

반응식

HRID 1961623 반응식
Cl.[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH2:13])[CH2:9][CH2:8]1)[CH3:3].Cl.[N:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([C:26]([Cl:28])=[O:27])=[CH:18][CH:17]=1.C(N(CC)CC)C.CCCCCCC.CCOC(C)=O>ClCCl.CCOC(C)=O>[ClH:28].[CH2:2]([O:4][C:5](=[O:14])[CH2:6][C@H:7]1[CH2:8][CH2:9][C@H:10]([NH:13][C:26]([C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:16]=[CH:17][CH:18]=2)=[O:27])[CH2:11][CH2:12]1)[CH3:3]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 12373997Quinoline-4-carbonyl chloride hydrochlorideHCID 21899848Ethylacetate heptaneHCID 178471807HCID 178471807, 화합물

생성물 1

HCID 178471809HCID 178471809, 화합물수율 42%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of Trans-(4-Amino-cyclohexyl)-acetic acid ethyl ester hydrochloride (3.63 g, 17 mmol) is solved in dichloromethane (115 mL) and quinoline-4-carbonyl chloride hydrochloride is added (4.184 g, 18 mmol) followed by the slow addition of triethylamine (11.3 mL, 81 mmol) at 0° C. The mixture is stirred at room temperature overnight and the salts obtained are removed by filtration and the filtrate is extracted. The organic layer is washed with NaHCO3 and brine. The organic phases are dried and concentrated to obtain 3.8 g of a crude. After a flash chromatography with heptane/AcOEt 4:1 to AcOEt a solid was obtained that was recrystallized with EtOAc and n-heptane to obtain the title compound as a pink solid (2.72 g, 42% yield). MS (m/e): 341.3 (M+H+).

후처리

  1. customthe salts obtained
  2. customare removed by filtration
  3. extractionthe filtrate is extracted
  4. washThe organic layer is washed with NaHCO3 and brine
  5. customThe organic phases are dried
  6. concentrationconcentrated
  7. customto obtain 3.8 g of a crude
  8. customthat was recrystallized with EtOAc and n-heptane

출처 및 근거

ORD 기록
ord-5198bdffeefc4d6abc54345b79c623f9
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415350B2

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