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

HRID 1066749노트

반응식

HRID 1066749 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3e546895a148415e9ad3d662cf202b73
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06245769B1

반응 노트

불러오는 중…