Trichloroacetyl isocyanate → [5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methyl carbamate

HRID 1862466ノート

反応式

HRID 1862466 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[N:13]=[C:12]([CH2:18][OH:19])[C:11]=2[CH2:20][C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.ClC(Cl)(Cl)[C:29]([N:31]=C=O)=[O:30]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:10]2[N:14]([CH:15]([CH3:17])[CH3:16])[N:13]=[C:12]([CH2:18][O:19][C:29](=[O:30])[NH2:31])[C:11]=2[CH2:20][C:21]2[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

4

反応物 2

HCID 76400Trichloroacetyl isocyanateHCID 514441[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methanol

生成物 1

HCID 514442[5-(3,5-Dichlorophenyl)sulfanyl-1-isopropyl-4-(4-pyridylmethyl)pyrazol-3-yl]methyl carbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution containing 100 mg of 5-(3,5-dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methyl]-1H-pyrazole-3-methanol in 3 ml of anhydrous dichloromethane was stirred under nitrogen at 0° C. while 35 μl of trichloroacetyl isocyanate was added dropwise. The mixture was stirred at 0° C. for 2 h. The mixture was evaporated under reduced pressure and then the residue was treated with 2 ml of methanol, 1 ml water and 100 mg of potassium carbonate under nitrogen at 0° C. The mixture was then stirred at room temperature for 1 h. The mixture was partitioned between ethyl acetate and water then extracted with ethyl acetate three times. The combined extracts were washed with brine then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using methanol/dichloromethane (1:49) for the elution to give 67 mg of carbamic acid [5-(3,5-dichlorophenylthio)-1-isopropyl-4-[(4-pyridyl)methyl]-1H-pyrazol-3-yl]methyl ester as a white solid. Mass spectrum (ESI) m/z 451 [M+H]+. 1H NMR (DMSO) 1.30 (d, 6H), 3.91 (s, 2H), 4.77 (m, 1H), 5.05 (s, 2H), 6.55 (br s, 1H), 6.78 (br s, 1H), 6.79 (s, 2H), 7.08 (d, 2H), 7.39 (s, 1H), 8.30 (d, 2H).

後処理

  1. additionwas added dropwise
  2. customThe mixture was evaporated under reduced pressure
  3. additionthe residue was treated with 2 ml of methanol, 1 ml water and 100 mg of potassium carbonate under nitrogen at 0° C
  4. stirringThe mixture was then stirred at room temperature for 1 h
  5. customThe mixture was partitioned between ethyl acetate and water
  6. extractionthen extracted with ethyl acetate three times
  7. washThe combined extracts were washed with brine
  8. dry with materialthen dried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by flash chromatography on silica gel
  12. washfor the elution

出典と根拠

ORDレコード
ord-7578375e63044b6eb814edfbadf20d8f
出典データセット
uspto-grants-2003_03
特許番号
US06538015B1

反応ノート

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