Pyridine → [5-(1-Methyl-cyclopropyl)-2-(6-methyl-pyridin-3-yl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 1993676ノート

反応式

HRID 1993676 の反応式
[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](Cl)=[O:6].F[C:11](F)(F)[C:12]1([C:15]2[CH:16]=[C:17]([NH2:27])[N:18]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=C[CH:21]=3)[N:19]=2)[CH2:14][CH2:13]1.[N:30]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C1COCC1.ClCCl>[Cl:1][C:2]([Cl:9])([Cl:8])[CH2:3][O:4][C:5](=[O:6])[NH:27][C:17]1[N:18]([C:20]2[CH:21]=[N:30][C:23]([CH3:26])=[CH:24][CH:25]=2)[N:19]=[C:15]([C:12]2([CH3:11])[CH2:13][CH2:14]2)[CH:16]=1

参加物

7

反応物 4

HCID 1049PyridineHCID 870632,2,2-Trichloroethyl chloroformateHCID 516892Sodium BicarbonateHCID 668765651-p-tolyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

生成物 1

HCID 68538118[5-(1-Methyl-cyclopropyl)-2-(6-methyl-pyridin-3-yl)-2H-pyrazol-3-yl]-carbamic acid 2,2,2-trichloro-ethyl ester収率 75.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-15 °C

実験手順

Add a solution of 2,2,2-trichloroethylchloroformate (1.80 g, 8.5 mmol) in THF (10 mL) dropwise to an ice-salt cooled solution of 5-(1-trifluoromethyl-cyclopropyl)-2-p-tolyl-2H-pyrazol-3-ylamine (2.29 g, 8.1 mmol) and pyridine (0.9 mL, 11 mmol) in THF (30 mL) at −15° C. Stir at −15° C. for 0.5 hours and then 22° C. for 1 hour, then distribute the reaction mixture between dichloromethane (50 mL) and a saturated aq. sodium bicarbonate solution (50 mL). Isolate the aqueous phase and extract twice with dichloromethane (25 mL each). Dry the combined organic phases over sodium sulfate and concentrate. Subject residue to silica gel chromatography eluting with hexanes and ethyl acetate to give a white solid (2.46 g, 66% yield). MS(ES+): m/z=457.2 [M+H].

後処理

  1. wait22° C. for 1 hour
  2. customIsolate the aqueous phase
  3. extractionextract twice with dichloromethane (25 mL each)
  4. dry with materialDry the combined organic phases over sodium sulfate
  5. concentrationconcentrate
  6. washSubject residue to silica gel chromatography eluting with hexanes and ethyl acetate

出典と根拠

ORDレコード
ord-984b9d82af544506a7f3a2f375157f9f
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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