Triethylamine → HCID 178471809、化合物

HRID 1714404ノート

反応式

HRID 1714404 の反応式
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]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 12373997Quinoline-4-carbonyl chloride hydrochlorideHCID 21899848Ethylacetate heptaneHCID 178471807HCID 178471807、化合物

生成物 1

HCID 178471809HCID 178471809、化合物収率 42%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-fb36118e226b43b9ae54edaa3998f0ad
出典データセット
uspto-grants-2010_09
特許番号
US07795437B2

反応ノート

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