Trifluoroacetic acid → 5-(3-chloro-benzylamino)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

HRID 1024319ノート

反応式

HRID 1024319 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[N:7]=[C:8]([NH2:10])[CH:9]=1)=[O:4].[Cl:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(#N)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH3:11])[N:7]=[C:8]([NH:10][CH2:16][C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([Cl:12])[CH:14]=2)[CH:9]=1)=[O:4]

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 114773-ChlorobenzaldehydeHCID 12052TriethylsilaneHCID 13248993methyl 3-amino-1-methyl-1H-pyrazole-5-carboxylate

生成物 1

HCID 576194175-(3-chloro-benzylamino)-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

5-Amino-2-methyl-2H-pyrazole-3-carboxylic acid methyl ester (644, 1.3 g, 8.0 mmol) was combined with 3-chlorobenzaldehyde (645, 0.95 mL, 8.4 mmol) and acetonitrile (40 mL). Trifluoroacetic acid (3.2 mL, 42.0 mmol) was added followed by triethylsilane (6.7 mL, 42.0 mmol). The reaction was heated to reflux overnight and then concentrated. Ethyl acetate was added and the solution was washed with 1N potassium carbonate. The organic portion was dried over anhydrous sodium sulfate, filtered and concentrated. The compound (646, 0.944 g, 42%) was crystallized from a mixture of ethyl acetate:hexane.

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. additionEthyl acetate was added
  5. washthe solution was washed with 1N potassium carbonate
  6. dry with materialThe organic portion was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe compound (646, 0.944 g, 42%) was crystallized from a mixture of ethyl acetate

出典と根拠

ORDレコード
ord-1de95e691942413cbb01a03d9af0a4f8
出典データセット
uspto-grants-2014_05
特許番号
US08722702B2

反応ノート

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