Ethanamine, 2-fluoro-, hydrochloride → N-(2-chloroethyl)-(3-benzyl-5,6-diethylpyrazine-2-yl oxy) acetamide

HRID 330070

반응식

HRID 330070 반응식
[C:1](Cl)(=[O:6])[C:2](C)(C)C.C(O[O:12][C:13]1[C:18]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:17][C:16]([CH2:26][CH3:27])=[C:15]([CH2:28][CH3:29])[N:14]=1)(=O)C.[ClH:30].F[CH2:32][CH2:33][NH2:34].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(N(CC)CC)C.C(Cl)(Cl)Cl>[Cl:30][CH2:32][CH2:33][NH:34][C:1](=[O:6])[CH2:2][O:12][C:13]1[C:18]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[N:17][C:16]([CH2:26][CH3:27])=[C:15]([CH2:28][CH3:29])[N:14]=1

참가 물질

8

반응물 4

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 11430Potassium CarbonateHCID 62493Pivaloyl chlorideHCID 86743689(3-Benzyl-5,6-diethylpyrazine-2-yl oxy) acetate

생성물 1

HCID 15170451N-(2-chloroethyl)-(3-benzyl-5,6-diethylpyrazine-2-yl oxy) acetamide수율 88.8%

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매2회

실험 절차

Pivaloyl chloride (3.66 g, 30 mM) was added dropwise at -5° C. to compound 655 (8.62 g, 28.7 mM) and triethylamine (4.2 ml, 30 mM) dissolved in tetrahydrofuran (50 ml), then the mixture was stirred for 30 minutes. Chloroform (30 ml) in solution with 2-fluoroethylamine hydrochloride (3.48 g) and triethylamine (4.2 ml) was added dropwise thereto with cooling at 0° to -5° C. then the mixture was stirred for 1 hour with ice cooling and 4 hours at room temperature. Dilute aqueous potassium carbonate was added to the reaction mixture and the mixture was extracted three times with chloroform. The extract was dried with anhydrous magnesium sulfate, and concentrated in vacuo. The residue was charged on a column of silica gel (C-200, 175 g) and eluted successively with benzene and benzene-ethyl acetate (5:1) to obtain the product. (9.21 g, yield: 88.8%).

후처리

  1. temperaturewith cooling at 0° to -5° C.
  2. stirringthe mixture was stirred for 1 hour with ice cooling and 4 hours at room temperature
  3. extractionthe mixture was extracted three times with chloroform
  4. dry with materialThe extract was dried with anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. additionThe residue was charged on a column of silica gel (C-200, 175 g)
  7. washeluted successively with benzene and benzene-ethyl acetate (5:1)
  8. customto obtain the product

출처 및 근거

ORD 기록
ord-fd7256a37c514635bd620f41b69d38a7
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04894453

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