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

HRID 574240ノート

反応式

HRID 574240 の反応式
[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

参加物

4

反応物 2

HCID 27592641,1,1,4,4,4-Hexafluoro-2,3-butanedioneHCID 12439913HCID 12439913、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-641da2f31c76452d92b852fee5621d8d
出典データセット
uspto-grants-2015_05
特許番号
US09034879B2

反応ノート

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