Triethylamine → HCID 178471809、化合物

HRID 1961623ノート

反応式

HRID 1961623 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.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]

参加物

7

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 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-5198bdffeefc4d6abc54345b79c623f9
出典データセット
uspto-grants-2013_04
特許番号
US08415350B2

反応ノート

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