Benzylamine → 4-(3-Benzylamino-2-cyano-6-fluoro-phenyl)-piperazine-1-carboxylic Acid Tert-butyl Ester

HRID 901877노트

반응식

HRID 901877 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16](F)[C:15]=2[C:22]#[N:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:19]([F:20])=[CH:18][CH:17]=[C:16]([NH:37][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:15]=2[C:22]#[N:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 58901904HCID 58901904, 화합물

생성물 1

HCID 588241264-(3-Benzylamino-2-cyano-6-fluoro-phenyl)-piperazine-1-carboxylic Acid Tert-butyl Ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To 655 mg (2.03 mmol) of 4-(2-cyano-3,6-difluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester dissolved in 10 mL DMF was added 560 mg (2 eq., 4.06 mmol) potassium carbonate and 243 μL (1.1 eq., 2.22 mmol) benzylamine. The mixture was heated to 100° C. for 5 days, cooled to room temperature and partitioned between ethyl acetate and water, dried over magnesium sulfate and concentrated. 4-(3-Benzylamino-2-cyano-6-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (288 mg) was precipitated from dichloromethane/hexanes.

후처리

  1. temperaturecooled to room temperature
  2. custompartitioned between ethyl acetate and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. custom4-(3-Benzylamino-2-cyano-6-fluoro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (288 mg) was precipitated from dichloromethane/hexanes

출처 및 근거

ORD 기록
ord-42b5d5ab499e413f8decd1bbe161b5c8
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365063B2

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