1,4-Dioxane → N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-1-methyl-3-(pentafluoroethyl)-4-iodo-1H-pyrazole-5-carboxamide

HRID 1843059ノート

反応式

HRID 1843059 の反応式
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9](=[O:14])[NH:10][CH:11]1[CH2:13][CH2:12]1.[I:15][C:16]1[C:17]([C:25]([F:31])([F:30])[C:26]([F:29])([F:28])[F:27])(C(O)=O)[NH:18][N:19]([CH3:21])[CH:20]=1.Cl.C(N=C=NCCCN(C)C)C.[O:44]1CCOC[CH2:45]1>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:45]([C:20]2[N:19]([CH3:21])[N:18]=[C:17]([C:25]([F:30])([F:31])[C:26]([F:27])([F:28])[F:29])[C:16]=2[I:15])=[O:44])=[CH:4][C:3]=1[C:9](=[O:14])[NH:10][CH:11]1[CH2:13][CH2:12]1

参加物

5

反応物 4

HCID 312751,4-Dioxane2 回HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 167752405-amino-2-chloro-N-cyclopropylbenzamideHCID 866600834-iodo-1-methyl-3-pentafluoroethyl-1H-pyrazolecarboxylic acid

生成物 1

HCID 46219667N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-1-methyl-3-(pentafluoroethyl)-4-iodo-1H-pyrazole-5-carboxamide

実験手順

0.49 g (2.34 mmol) of 4-chloro-3-(cyclopropylcarbamoyl)aniline dissolved in 0.5 ml of dioxane are added dropwise to a solution of 1.28 g (2.34 mmol) of 4-iodo-1-methyl-3-pentafluoroethyl-1H-pyrazolecarboxylic acid and 0.54 g (2.81 mmol) of 1-ethyl-3-[3-dimethylaminopropyl]carbodiimide hydrochloride in 20 ml of dioxane and the reaction mixture is stirred for three days at room temperature. The majority of the dioxane is distilled off at reduced pressure on a rotary evaporator and the residue is admixed with 20 ml of water. The aqueous phase is extracted three times with ethyl acetate and the organic phase is then washed three times with saturated sodium chloride solution. After drying over sodium sulphate, the solvent is distilled off at reduced pressure on a rotary evaporator and the residue is purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate). This gives 0.70 g of N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-1-methyl-3-(pentafluoroethyl)-4-iodo-1H-pyrazole-5-carboxamide (53%) as an oil.

後処理

  1. distillationThe majority of the dioxane is distilled off at reduced pressure on a rotary evaporator
  2. extractionThe aqueous phase is extracted three times with ethyl acetate
  3. washthe organic phase is then washed three times with saturated sodium chloride solution
  4. dry with materialAfter drying over sodium sulphate
  5. distillationthe solvent is distilled off at reduced pressure on a rotary evaporator
  6. customthe residue is purified by means of flash chromatography on silica gel (eluent: cyclohexane/ethyl acetate)

出典と根拠

ORDレコード
ord-8e1cd3f73fae409891f031f295b06659
出典データセット
uspto-grants-2015_02
特許番号
US08946234B2

反応ノート

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