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

HRID 330806ノート

反応式

HRID 330806 の反応式
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

参加物

7

反応物 4

HCID 531671-MethylpiperazineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl2 回HCID 18407952Tripotassium phosphate trihydrateHCID 584963413-[3-(5-iodopyrimidin-2-yl)benzyl]-5-trifluoromethyl-3H-benzothiazol-2-one

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-15da7088dc4548dc898013bf70f4bbf6
出典データセット
uspto-grants-2014_11
特許番号
US08877751B2

反応ノート

読み込み中…