Dimethylformamide → N-[4-chloro-2-hydroxy-3-sulfamylphenyl]-N'-(4-methyl-cyclohexyl) urea

HRID 432609

反応式

HRID 432609 の反応式
C[CH:2]1[CH2:7][CH2:6][CH:5]([C:8](O)=O)[CH2:4][CH2:3]1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.[NH2:28][C:29]1[C:30]([OH:40])=[C:31]([S:36]([NH2:39])(=[O:38])=[O:37])[C:32]([Cl:35])=[CH:33][CH:34]=1.C[N:42]([CH:44]=[O:45])C>>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([NH:28][C:44]([NH:42][CH:2]2[CH2:3][CH2:4][CH:5]([CH3:8])[CH2:6][CH2:7]2)=[O:45])=[C:30]([OH:40])[C:31]=1[S:36](=[O:38])(=[O:37])[NH2:39]

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 203304-Methylcyclohexanecarboxylic acidHCID 199401P,P-Diphenylphosphinic azideHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

生成物 1

HCID 9968924N-[4-chloro-2-hydroxy-3-sulfamylphenyl]-N'-(4-methyl-cyclohexyl) urea

反応条件

温度
80 °C

実験手順

To a solution of 4-Methyl-cyclohexanecarboxylic acid (0.141 mL) in DMF (0.5 mL) was added DPPA (0.215 mL) and TEA (0.139 mL) and the reaction heated at 80° C. After 18 hrs, 3-Amino-6-chloro-2-hydroxy-benzenesulfonamide (0.150 g) was added and the reaction heated at 80° C. After 18 hrs, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layers were dried over anhydrous magnesium sulfate, and concentraed under reduced pressure. The crude residue was purified via HPLC to give 15 mg of N-[4-chloro-2-hydroxy-3-sulfamylphenyl]-N′-(4-methyl-cyclohexyl) urea. LC-MS (m/z) 347 (M+).

後処理

  1. temperaturethe reaction heated at 80° C
  2. waitAfter 18 hrs
  3. customthe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  6. customThe crude residue was purified via HPLC

出典と根拠

ORDレコード
ord-e00e51ccbea146c6b400862721699a3e
出典データセット
uspto-grants-2003_12
特許番号
US06664259B2

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