1-Methylpiperazine → 3-{3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]benzyl}-5-trifluoromethyl-3H-benzothiazol-2-one

HRID 330806노트

반응식

HRID 330806 반응식
I[C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([CH:26]=[CH:27][CH:28]=2)[CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:19]=[CH:20][C:15]=3[S:14][C:13]2=[O:25])=[N:6][CH:7]=1.[CH3:29][N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1.O>[CH3:29][N:30]1[CH2:35][CH2:34][N:33]([C:2]2[CH:3]=[N:4][C:5]([C:8]3[CH:9]=[C:10]([CH:26]=[CH:27][CH:28]=3)[CH2:11][N:12]3[C:16]4[CH:17]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:19]=[CH:20][C:15]=4[S:14][C:13]3=[O:25])=[N:6][CH:7]=2)[CH2:32][CH2:31]1

참가 물질

7

반응물 4

HCID 531671-MethylpiperazineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl2회HCID 18407952Tripotassium phosphate trihydrateHCID 584963413-[3-(5-iodopyrimidin-2-yl)benzyl]-5-trifluoromethyl-3H-benzothiazol-2-one

생성물 1

HCID 468467263-{3-[5-(4-methylpiperazin-1-yl)pyrimidin-2-yl]benzyl}-5-trifluoromethyl-3H-benzothiazol-2-one

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

513 mg (1 mmol) of 3-[3-(5-iodopyrimidin-2-yl)benzyl]-5-trifluoromethyl-3H-benzothiazol-2-one is suspended in toluene, briefly heated to 100° C. and cooled to room temperature. 134 μl (1.2 mmol) of methylpiperazine, 297 mg (1.4 mmol) of potassium phosphate trihydrate, and 33 mg (0.08 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl and 18 mg (0.02 mmol) of tris(benzylideneacetone)dipalladium are subsequently added and stirred at 100° C. under an argon atmosphere. 33 mg (0.08 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl and 18 mg (0.02 mmol) of tris(benzylideneacetone)dipalladium are subsequently again added and stirred at 100° C. for a further 24 h under an argon atmosphere. Water is added to the reaction mixture, which is then extracted with ethyl acetate and dried. The crude product is purified by means of preparative HPLC. The product is in the form of the trifluoroacetate.

후처리

  1. temperaturecooled to room temperature
  2. stirringstirred at 100° C. for a further 24 h under an argon atmosphere
  3. extractionis then extracted with ethyl acetate
  4. customdried
  5. customThe crude product is purified by means of preparative HPLC

출처 및 근거

ORD 기록
ord-15da7088dc4548dc898013bf70f4bbf6
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877751B2

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