Acetic Acid → [2-(6-Methoxy-[1,5]naphthyridin-4-yl)-ethyl]-methyl-amine

HRID 1640527

反応式

HRID 1640527 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[C:6]([CH:13]=[CH2:14])[CH:7]=[CH:8][N:9]=2)[N:4]=1.Cl.[CH3:16][NH2:17].CC(O)=O>CO>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[CH2:13][CH2:14][NH:17][CH3:16]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 6364545Methylamine hydrochlorideHCID 575995738-Ethenyl-2-methoxy-1,5-naphthyridine

生成物 1

HCID 66737803[2-(6-Methoxy-[1,5]naphthyridin-4-yl)-ethyl]-methyl-amine収率 19%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 2-methoxy-8-vinyl-[1,5]naphthyridine (prepared as in WO 02/08224; 0.28 g, 1.5 mmol) in MeOH (6 mL) was treated with methyl amine hydrochloride (0.1 g, 1 eq.) and heated in a sealed flask at reflux for 5 h. AcOH (0.9 mL) was added and the mixture heated at reflux overnight. The mixture was concentrated in vacuo, taken up in aq. ammonia and extracted with DCM/MeOH (9:1). The combined org. extracts were dried over MgSO4 and concentrated. The residue was purified by FC (DCM/MeOH 9:1+1% NH4OH) to give the title amine as a brown oil (0.06 g, 19% yield).

後処理

  1. temperatureheated in a sealed flask
  2. temperatureat reflux for 5 h
  3. temperaturethe mixture heated
  4. temperatureat reflux overnight
  5. concentrationThe mixture was concentrated in vacuo
  6. extractionextracted with DCM/MeOH (9:1)
  7. dry with materialextracts were dried over MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by FC (DCM/MeOH 9:1+1% NH4OH)

出典と根拠

ORDレコード
ord-4cf662d8b700426b9368161314950e1e
出典データセット
uspto-grants-2012_02
特許番号
US08114867B2

関連ノート

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