Triethylamine → HCID 178471809, 화합물

HRID 1714404노트

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HRID 1714404 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.C(OCC)(=O)C>ClCCl>[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

6

반응물 4

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

생성물 1

HCID 178471809HCID 178471809, 화합물수율 42%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of Trans-(4-Amino-cyclohexyl)-acetic acid ethyl ester hydrochloride (3.63 g, 17 mmol) was solved in dichloromethane (115 mL) and quinoline-4-carbonyl chloride hydrochloride was added (4.184 g, 18 mmol) followed by the slow addition of triethylamine (11.3 mL, 81 mmol) at 0° C. The mixture was stirred at room temperature overnight and the salts obtained are removed by filtration and the filtrate was extracted. The organic layer was 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/ethyl acetate 4:1 a solid was obtained that was recrystallized with ethyl acetate 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 was extracted
  4. washThe organic layer was 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 ethyl acetate and n-heptane

출처 및 근거

ORD 기록
ord-fb36118e226b43b9ae54edaa3998f0ad
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07795437B2

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