Acetic Acid → (S)-3-amino-2-chloro-4-N-(1-methoxymethyl-3-methoxypropyl)-6-methyl-pyridin-4-amine

HRID 1066749ノート

反応式

HRID 1066749 の反応式
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([NH:11][CH:12]([CH2:17][O:18][CH3:19])[CH2:13][CH2:14][O:15][CH3:16])[CH:5]=[C:4]([CH3:20])[N:3]=1.C(O)(=O)C>CO.[Fe]>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([CH3:20])=[CH:5][C:6]=1[NH:11][C@H:12]([CH2:17][O:18][CH3:19])[CH2:13][CH2:14][O:15][CH3:16]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 186292362-Chloro-6-methyl-3-nitro-N-(1-methoxymethyl-3-methoxypropyl)pyridin-4-amine

生成物 1

HCID 54034668(S)-3-amino-2-chloro-4-N-(1-methoxymethyl-3-methoxypropyl)-6-methyl-pyridin-4-amine

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 887Methanol溶媒

実験手順

2—Chloro-6-methyl-3-nitro-N-(1-methoxymethyl-3-methoxypropyl)pyridin-4-amine (˜16.82 mmol) was heated at reflux with Fe powder (10 g) in methanol (120 mL) in the presence of glacial acetic acid (10 mL) for 2 h. Then the iron was filtered through celite, the celite was washed with methanol(80 mL) and the filtrate was stripped in vacuo. The residue was dissolved in 10% HCl (120 mL) and EtOAc was added (160 mL). The mixture was neutralized with solid NaHCO3 and the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4) and stripped in vacuo (4.1 g).

後処理

  1. filtrationThen the iron was filtered through celite
  2. washthe celite was washed with methanol(80 mL)
  3. dissolutionThe residue was dissolved in 10% HCl (120 mL)
  4. additionEtOAc was added (160 mL)
  5. extractionthe aqueous layer was extracted with EtOAc (2×100 mL)
  6. washThe combined organic extracts were washed with brine (50 mL)
  7. dry with materialdried (MgSO4)

出典と根拠

ORDレコード
ord-3e546895a148415e9ad3d662cf202b73
出典データセット
uspto-grants-2001_06
特許番号
US06245769B1

反応ノート

読み込み中…