2-(Ethoxymethylene)propanedinitrile → 5-amino-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbonitrile

HRID 719469

반응식

HRID 719469 반응식
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][NH2:13].C[O-].[Na+].C(O[CH:20]=[C:21]([C:24]#[N:25])[C:22]#[N:23])C>CO>[NH2:25][C:24]1[N:12]([C:3]2[CH:4]=[CH:5][C:6]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:7][C:2]=2[F:1])[N:13]=[CH:20][C:21]=1[C:22]#[N:23]

참가 물질

5

반응물 3

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 2782739[2-Fluoro-4-(methylsulfonyl)phenyl]hydrazineHCID 10942334Sodium Methoxide

생성물 1

HCID 218975935-amino-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbonitrile수율 87.6%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(2-Fluoro-4-methanesulfonyl-phenyl)-hydrazine (1 g, 4.89 mmol) and sodium methoxide (30 mg, 0.489 mmol) were dissolved in methanol under N2 at room temperature. The mixture was stirred for 10 min and 2-ethoxymethylene-malononitrile (0.6 g, 4.91 mmol) was added. The reaction mixture was stirred for 30 min and then brought to reflux for 2 hours. The solvent was removed under reduced pressure; the residue was suspended in water and extracted with ethyl acetate. The organic layer was washed with water, brine and was dried over sodium sulfate. The solvent was concentrated, affording 5-amino-1-(2-fluoro-4-methanesulfonyl-phenyl)-1H-pyrazole-4-carbonitrile as a yellow solid (1.2 g, 87.5%). 1H NMR (400 MHz DMSO-d6) δ (ppm): 7.96 (d, 1H); 7.93 (m, 1H); 7.80 (s, 1H); 7.74 (m, 1H); 6.89 (s, 2H); 3.24(s, 3H). Exact mass calculated for C11H9FN4O2S 280.04, found 281.30 (MH+, 100%).

후처리

  1. stirringThe reaction mixture was stirred for 30 min
  2. temperatureto reflux for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water, brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationThe solvent was concentrated

출처 및 근거

ORD 기록
ord-bad1eeaec5ad447cab7d2a835c534d9d
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132426B2

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