Pyridine → [5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloroethyl ester

HRID 1993678ノート

反応式

HRID 1993678 の反応式
[CH3:1][C:2]1([C:5]2[CH:6]=[C:7]([NH2:17])[N:8]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[N:9]=2)[CH2:4][CH2:3]1.N1C=CC=CC=1.Cl[C:25]([O:27][CH2:28][C:29]([Cl:32])([Cl:31])[Cl:30])=[O:26].ClC([O-])=O>C1COCC1.O>[Cl:30][C:29]([Cl:32])([Cl:31])[CH2:28][O:27][C:25](=[O:26])[NH:17][C:7]1[N:8]([C:10]2[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=2)[N:9]=[C:5]([C:2]2([CH3:1])[CH2:3][CH2:4]2)[CH:6]=1

参加物

7

反応物 4

HCID 1049Pyridine2 回HCID 870632,2,2-Trichloroethyl chloroformateHCID 21226386CarbonochloridateHCID 685368275-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine

生成物 1

HCID 57832815[5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloroethyl ester収率 81.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Treat a cooled (0° C.) solution of the 5-(1-methyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine (5.68 g, 25 mmol) and pyridine (2.2 mL, 27.5 mmol) in THF (3 mL/mmol) with 2,2,2-trichloroethyl chloroformate (3.7 mL, 27.5 mmol). Maintain the reaction temperature at 0° C., and after 2 hours, add small portions of chloroformate (0.3 mL) and pyridine (0.2 mL). One hour later, dilute the reaction with water (150 mL) and extract with EtOAc (3×100 mL). Wash the combined organic phases with water (100 mL), saturated aq. NaHCO3 (50 mL), and saturated aq. sodium chloride (50 mL). Recrystallize the crude syrup from ethyl acetate/hexanes to provide the title compound as a white solid (8.18 g, 20.3 mmol; 81%). LCMS (ES+): m/z=402.2/404.2 [M+H].

後処理

  1. additionTreat
  2. additionOne hour later, dilute
  3. extractionextract with EtOAc (3×100 mL)
  4. washWash the combined organic phases with water (100 mL), saturated aq. NaHCO3 (50 mL), and saturated aq. sodium chloride (50 mL)
  5. customRecrystallize the crude syrup from ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-e6bcf66624c14994875b5d5f0d5f30eb
出典データセット
uspto-grants-2010_01
特許番号
US07652015B2

反応ノート

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