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Trifluoroacetic acid → ethyl 5-amino-1-(4-ethoxy-2,6-difluorobenzyl)-4-methyl-1H-pyrazole-3-carboxylate

HRID 1484682
ノート
印刷プレビュー

反応式

HRID 1484682 の反応式
[C:1](/[C:3](/[CH3:11])=[C:4](\[O-])/[C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:2].[K+].FC(F)(F)C(O)=O.Cl.Cl.[CH2:22]([O:24][C:25]1[CH:33]=[C:32]([F:34])[C:28]([CH2:29][NH:30][NH2:31])=[C:27]([F:35])[CH:26]=1)[CH3:23]>O1CCOCC1>[NH2:2][C:1]1[N:30]([CH2:29][C:28]2[C:27]([F:35])=[CH:26][C:25]([O:24][CH2:22][CH3:23])=[CH:33][C:32]=2[F:34])[N:31]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]=1[CH3:11]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 24824588potassium (2Z)-3-cyano-1-ethoxy-1-oxobut-2-en-2-olateHCID 89647959(4-Ethoxy-2,6-difluorobenzyl)hydrazine dihydrochloride

生成物 1

HCID 89662197ethyl 5-amino-1-(4-ethoxy-2,6-difluorobenzyl)-4-methyl-1H-pyrazole-3-carboxylate

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

2.01 g potassium (2Z)-3-cyano-1-ethoxy-1-oxobut-2-en-2-olate (10.9 mmol, 1.0 eq.) were dissolved in dioxane at rt and 1.34 mL trifluoroacetic acid (17.4 mmol, 1.6 eq.) were added within 2 minutes. The slurry was stirred for 10 minutes and 3.00 g (4-ethoxy-2,6-difluorobenzyl)hydrazine dihydrochloride (10.9 mmol, 1.0 eq.) were added. The reaction mixture was stirred at 130° C. for 3 hours. The resulting solid was filtered off and washed rinsed with dioxane. The filtrate was partitioned between ethyl acetate and water. The aqueous phase was washed with ethyl acetate three times. The collected organic solutions were washed with brine, dried over a silicon filter, concentrated in vacuo and purified by flash chromatography: 1.10 g (2.42 mmol, 22%) of a 71% pure target compound.

後処理

  1. stirringThe reaction mixture was stirred at 130° C. for 3 hours
  2. filtrationThe resulting solid was filtered off
  3. washwashed
  4. washrinsed with dioxane
  5. customThe filtrate was partitioned between ethyl acetate and water
  6. washThe aqueous phase was washed with ethyl acetate three times
  7. washThe collected organic solutions were washed with brine
  8. customdried over a silicon
  9. filtrationfilter
  10. concentrationconcentrated in vacuo
  11. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-65d4bc075de044fd89e2365fa25c3a31
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09422268B2

反応ノート

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