Ammonium Chloride → (+/-)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine

HRID 2409012ノート

反応式

HRID 2409012 の反応式
[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([C:20](=[N:22]O)[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[NH4+].[Cl-]>CO.CC(O)=O.[Zn]>[S:1]([N:11]1[C:19]2[CH:18]=[CH:17][N:16]=[C:15]([CH:20]([NH2:22])[CH3:21])[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:3])=[O:2]

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 1364090991-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime

生成物 1

HCID 86689823(+/-)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine収率 87.4%

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
80 °C

実験手順

A mixture of 1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanone oxime (1.29 g, 3.92 mmol), zinc (2.55 g, 39.2 mmol), and NH4Cl (2.10 mg, 39.2 mmol) in MeOH (5 mL) and HOAc (3 mL) was stirred at 80° C. for 4 h. The mixture was cooled to RT and the solid filtered. The filtrate was concentrated under reduced pressure. To the residue was added ammonia solution (50 mL) and the reaction mixture was extracted with DCM (3×50 mL). The combined organic extracts were concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with DCM/MeOH/TEA (15:1:0.2) to afford 1.08 g (87.4%) (±)-1-(1-tosyl-1H-pyrrolo[3,2-c]pyridin-4-yl)ethanamine as a yellow solid: MS (ESI) m/z: 316.2 [M+1]+.

後処理

  1. temperatureThe mixture was cooled to RT
  2. filtrationthe solid filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. additionTo the residue was added ammonia solution (50 mL)
  5. extractionthe reaction mixture was extracted with DCM (3×50 mL)
  6. concentrationThe combined organic extracts were concentrated under reduced pressure
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with DCM/MeOH/TEA (15:1:0.2)

出典と根拠

ORDレコード
ord-69fc62f6eb1344dabe255071613d6ecf
出典データセット
uspto-grants-2014_08
特許番号
US08815877B2

反応ノート

読み込み中…