1,1,1,4,4,4-Hexafluoro-2,3-butanedione → Ethyl 3-amino-5,6-bis(trifluoromethyl)pyrazine-2-carboxylate

HRID 574240노트

반응식

HRID 574240 반응식
[CH2:1]([O:3][C:4](=[O:10])[CH:5]([NH2:9])[C:6](=[NH:8])[NH2:7])[CH3:2].[F:11][C:12]([F:22])([F:21])[C:13](=O)[C:14](=O)[C:15]([F:18])([F:17])[F:16]>CN(C=O)C>[NH2:8][C:6]1[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:10])=[N:9][C:14]([C:15]([F:18])([F:17])[F:16])=[C:13]([C:12]([F:22])([F:21])[F:11])[N:7]=1

참가 물질

4

반응물 2

HCID 27592641,1,1,4,4,4-Hexafluoro-2,3-butanedioneHCID 12439913HCID 12439913, 화합물

생성물 1

HCID 86657667Ethyl 3-amino-5,6-bis(trifluoromethyl)pyrazine-2-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of amino-carbamimidoyl-acetic acid ethyl ester (Int E2)(1.25 g, 8.61 mmol) in DMF (5 ml) was added 1,1,1,4,4,4-hexafluorobutane-2,3-dione (5 g, 25.8 mmol) and the mixture was stirred at RT for 25 days. The yellow suspension was partitioned between EtOAc (50 ml) and water (50 ml) and the organic portion was washed with brine (30 ml), dried (MgSO4) and concentrated in vacuo. The crude product was purified by mass directed LC-MS eluting with MeCN/Water/0.1% TFA. The clean fractions were poured into EtOAc (50 ml) and washed with saturated NaHCO3 (50 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound; 19F NMR (400 MHz, DMSO-d6): Peak 1 at −62 ppm, peak 2 at −64.6 ppm

후처리

  1. customThe yellow suspension was partitioned between EtOAc (50 ml) and water (50 ml)
  2. washthe organic portion was washed with brine (30 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by mass
  6. washeluting with MeCN/Water/0.1% TFA
  7. additionThe clean fractions were poured into EtOAc (50 ml)
  8. washwashed with saturated NaHCO3 (50 ml)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-641da2f31c76452d92b852fee5621d8d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034879B2

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