Ammonium Chloride → 3-((4-amino-1H-indazol-1-yl)methyl)-N,N-dimethylbenzamide

HRID 706679ノート

反応式

HRID 706679 の反応式
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[N:4]([CH2:14][C:15]2[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=2)[C:18]([N:20]([CH3:22])[CH3:21])=[O:19])[N:3]=1.[NH4+].[Cl-]>CO.[Zn]>[NH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:2]=[N:3][N:4]2[CH2:14][C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=1)[C:18]([N:20]([CH3:22])[CH3:21])=[O:19]

参加物

5

反応物 2

HCID 25517Ammonium ChlorideHCID 679762773-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-N,N-dimethylbenzamide

生成物 1

HCID 679763453-((4-amino-1H-indazol-1-yl)methyl)-N,N-dimethylbenzamide収率 61.2%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 887Methanol溶媒2 回

実験手順

A solution of 3-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-N,N-dimethylbenzamide (0.400 g, 0.888 mmol) and MeOH (8.8 mL) was cooled to 0° C. Zinc dust (0.290 g, 4.44 mmol) was added and the mixture was stirred vigorously for 15 minutes, followed by the dropwise addition of saturated aqueous NH4Cl (9 mL). The mixture was stirred vigorously for 15 minutes at 0° C. and then warmed to ambient temperature and stirred for an additional 1 hour. The mixture was diluted with MeOH and filtered. To the filtrate was added saturated aqueous NH4OAc and the mixture was concentrated to remove bulk MeOH. The mixture was extracted with EtOAc and the combined organic extracts were washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (2 to 20% IPA/CHCl3) to afford 0.160 g (61%) of the title compound as a yellow/orange solid.

後処理

  1. stirringThe mixture was stirred vigorously for 15 minutes at 0° C.
  2. stirringstirred for an additional 1 hour
  3. filtrationfiltered
  4. additionTo the filtrate was added saturated aqueous NH4OAc
  5. concentrationthe mixture was concentrated
  6. customto remove bulk MeOH
  7. extractionThe mixture was extracted with EtOAc
  8. washthe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was purified by column chromatography (2 to 20% IPA/CHCl3)

出典と根拠

ORDレコード
ord-9533a1c4596d44629597e203baa460ac
出典データセット
uspto-grants-2015_11
特許番号
US09174981B2

反応ノート

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