Dichloromethane → 1-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazole

HRID 610161ノート

反応式

HRID 610161 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]([OH:16])=O)=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:11]([C:22]([F:25])([F:24])[F:23])=[N:10]2)=[CH:5][CH:4]=1.[C:26](Cl)(=O)[C:27](Cl)=O.[CH2:32](Cl)Cl>CN(C)C=O.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[O:16][CH:32]=[CH:26][CH:27]=3)=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:11]([C:22]([F:23])([F:25])[F:24])=[N:10]2)=[CH:5][CH:4]=1

参加物

7

反応物 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 179399451-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-pyrazole-5-carboxylic acid

生成物 1

HCID 179399581-[(4-Methoxy)phenyl]-3-(trifluoromethyl)-4-(ethoxycarbonyl)-5-(2-furyl)pyrazole収率 70%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 142844-(Dimethylamino)pyridine触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 1-[(4-methoxy)phenyl]-3-(trifluoromethyl) -4-(ethoxycarbonyl)-pyrazole-5-carboxylic acid (0.5 g, 1.4 mmol) in 10 mL of methylene chloride was added oxalyl chloride (0.18 mL, 2.1 mmol) and 2 drops of dimethylformamide. The reaction was stirred at ambient temperature for 6 h and then the volatiles were removed in vacuo. The residue was dissolved in 20 mL of methylene chloride and then there was added 4-dimethylaminopyridine (0.51 g, 4.2 mmol). The reaction was stirred for 10 min and then there was added (2'-methylsulfonyl-3-fluoro -[1,1']-biphen-4-yl)amine hydrochloride (0.42 g, 1.4 mmol). The resulting mixture was allowed to stir at ambient temperature for 16 h. The reaction was diluted with ethyl acetate and the organics were washed with 10% aq HCl, sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated to afford 0.6 g (70%) of the compound of EXAMPLE 169 as a solid. A portion was purified by prep HPLC (C18 reverse phase column, elution with a H2O/CH3CN gradient with 0.5% TFA) and lyophilized to afford the title compound as a white powder. LRMS (ES+): 628.1 (M+Na)+.

後処理

  1. customthe volatiles were removed in vacuo
  2. dissolutionThe residue was dissolved in 20 mL of methylene chloride
  3. stirringThe reaction was stirred for 10 min
  4. stirringto stir at ambient temperature for 16 h
  5. washthe organics were washed with 10% aq HCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered through a pad of silica gel
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-54ef8511ca9e48c897fa3d1cfa87f868
出典データセット
uspto-grants-1999_12
特許番号
US05998424

反応ノート

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