Potassium Phosphate, Tribasic → 6-(2-Amino-6-chloro-pyrimidin-4-yloxy)-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

HRID 556356ノート

反応式

HRID 556356 の反応式
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[C:24]3[CH:25]=[CH:26][C:27]([OH:29])=[CH:28][C:23]=3[S:22][N:21]=2)=[O:19])=[CH:13][C:12]=1[C:30]([F:33])([F:32])[F:31].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN1C(=O)CCC1.CCOC(C)=O.O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[C:24]3[CH:25]=[CH:26][C:27]([O:29][C:6]4[CH:5]=[C:4]([Cl:9])[N:3]=[C:2]([NH2:1])[N:7]=4)=[CH:28][C:23]=3[S:22][N:21]=2)=[O:19])=[CH:13][C:12]=1[C:30]([F:32])([F:31])[F:33]

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 655222-Amino-4,6-dichloropyrimidineHCID 1363466286-Hydroxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

生成物 1

HCID 866266256-(2-Amino-6-chloro-pyrimidin-4-yloxy)-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
70 °C

実験手順

A mixture of 72 mg (0.44 mMol) 2-amino-4,6-dichloropyrimidine, 143 mg (0.40 mMol) 6-hydroxy-benzo[d]isothiazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide and 280 mg (1.32 mMol) K3PO4 in 2 ml NMP is stirred for 6 h at 70° C. Then the mixture is diluted with EtOAc and water, the aq. layer separated off and extracted twice with EtOAc. The organic phases are washed twice with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; CH2Cl2→CH2Cl2/EtOH 9:1) gives the title compound: MS: [M−1]=482/484; TLC(CH2Cl2): Rf=0.12.

後処理

  1. customthe aq. layer separated off
  2. extractionextracted twice with EtOAc
  3. washThe organic phases are washed twice with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-56155e3f1f6f49d6ba2a3284afad336f
出典データセット
uspto-grants-2011_11
特許番号
US08058276B2

反応ノート

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