Hydroxyamine hydrochloride → 4-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime

HRID 475230ノート

反応式

HRID 475230 の反応式
[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:17]=O.CC([O-])=O.[Na+].Cl.[NH2:25][OH:26]>CO>[F:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[CH:17]=[N:25][OH:26]

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866947324-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde

生成物 1

HCID 866947334-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime収率 71.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 148 (7.7 g, 0.031 mol) in dry MeOH (120 mL) was added NaOAc (3.31 g, 0.0372 moles) and hydroxylamine hydrochloride (2.57 g, 0.0372 mol). The reaction mixture was stirred at RT for 16 h. The solution was concentrated in vacuo, the residue taken up in water and extracted with DCM. The combined organic extracts were washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford 5.8 g (71%) of 4-fluoro-1-(tetrahydro-pyran-2-yl)-1H-benzoimidazole-5-carbaldehyde oxime (150) as a white solid which was used without further purification.

後処理

  1. concentrationThe solution was concentrated in vacuo
  2. extractionextracted with DCM
  3. washThe combined organic extracts were washed sequentially with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eece803e4ce342d5babeb597c9918e54
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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