Ammonium Chloride → 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanamine

HRID 2409053ノート

反応式

HRID 2409053 の反応式
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[N:14][C:15]([C:17](=[N:19]O)[CH3:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)=[CH:5][CH:4]=1.[Cl-].[NH4+]>CO.CC(O)=O.[Zn]>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:12]3[CH:13]=[N:14][C:15]([CH:17]([NH2:19])[CH3:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)=[CH:5][CH:4]=1

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 1364091021-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone oxime

生成物 1

HCID 866898631-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanamine収率 66%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

反応条件

温度
60 °C

実験手順

A mixture of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone oxime (320 mg, 1.08 mmol), zinc (3.53 g, 54.00 mmol), and ammonium chloride (2.89 g, 54.00 mmol) in MeOH (10 mL) and HOAc (2 mL) was heated at 60° C. for 4 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. To the residue was added an aqueous solution of ammonia (50 mL) and the resulting mixture was extracted with DCM (50 mL×3). The combined extracts were dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with CH2Cl2:MeOH:Et3N (10:1:0.2) to afford 200 mg (66%) of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanamine as a colorless oil. MS (ESI): m/z=283.2[M+1]+.

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added an aqueous solution of ammonia (50 mL)
  4. extractionthe resulting mixture was extracted with DCM (50 mL×3)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by SiO2 chromatography
  9. washeluting with CH2Cl2:MeOH:Et3N (10:1:0.2)

出典と根拠

ORDレコード
ord-67e5765c4033478eb9b26ffefdcf8aed
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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