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

HRID 1024319노트

반응식

HRID 1024319 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1de95e691942413cbb01a03d9af0a4f8
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722702B2

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