Hydroxyamine hydrochloride → 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone oxime

HRID 2409052ノート

反応式

HRID 2409052 の反応式
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[N:14][C:15]([C:17](=O)[CH3:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)=[CH:5][CH:4]=1.CC([O-])=O.[Na+].Cl.[NH2:28][OH:29]>CO>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[N:14][C:15]([C:17](=[N:28][OH:29])[CH3:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 866898611-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone

生成物 1

HCID 1364091021-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone oxime収率 61%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a mixture of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone (500 mg, 1.78 mmol) and NaOAc (1.21 g, 17.80 mmol) in MeOH (10 mL) at RT was added hydroxylamine hydrochloride (618 mg, 8.90 mmol). The reaction was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure. To the residue was added water (100 mL) followed by extraction with EtOAc (50 mL×3). The combined extracts were dried (MgSO4), filtered and concentrated under reduced pressure to afford 320 mg (61%) of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone oxime as a yellow solid. MS (ESI): m/z=297.2 [M+1]+.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionTo the residue was added water (100 mL)
  3. extractionfollowed by extraction with EtOAc (50 mL×3)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ef181a5caa6947b5a09ba2e79c58c601
出典データセット
uspto-grants-2014_08
特許番号
US08815877B2

反応ノート

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