Benzyloxyamine hydrochloride → 9,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c][1,5]naphthyridine

HRID 415519노트

반응식

HRID 415519 반응식
Cl[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1Cl)=[N:15][CH:14]=[CH:13][CH:12]=2)=O.Cl.C([O:27][NH2:28])C1C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)(C)C>[N:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[C:17]1[N:28]3[O:27][CH2:2][CH2:3][CH2:4][C:5]3=[N:7][C:8]=1[CH:9]=[N:10]2

참가 물질

5

반응물 3

HCID 102312Benzyloxyamine hydrochlorideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 66620109HCID 66620109, 화합물

생성물 1

HCID 666198299,10-dihydro-8H-[1,2]oxazino[2',3':1,2]imidazo[4,5-c][1,5]naphthyridine수율 5.2%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 4-chloro-N-(4-chloro[1,5]naphthyridin-3-yl)butanamide (3.1 g, 11 mmol) and O-benzylhydroxylamine hydrochloride (2.1 g, 13 mmol) in isopropanol (75 mL) was heated at reflux for 24 hours, then pyridinium p-toluenesulfonate (0.25 g, 1.0 mmol) was added and reflux continued for 48 more hours. The reaction mixture was then concentrated under reduced pressure and dichloromethane (50 mL) and saturated aqueous sodium carbonate (25 mL) were added and the mixture was stirred for 72 hours. The dichloromethane layer was then separated, concentrated under reduced pressure, and the residue purified by chromatography (silica gel eluted with 10% methanol in dichloromethane containing 5 mL of ammonium hydroxide solution per liter) to provide 0.13 g of 9,10-dihydro-8H-[1,2]oxazino[2′,3′:1,2]imidazo[4,5-c][1,5]naphthyridine.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. temperaturereflux
  4. concentrationThe reaction mixture was then concentrated under reduced pressure and dichloromethane (50 mL) and saturated aqueous sodium carbonate (25 mL)
  5. additionwere added
  6. customThe dichloromethane layer was then separated
  7. concentrationconcentrated under reduced pressure
  8. customthe residue purified by chromatography (silica gel eluted with 10% methanol in dichloromethane containing 5 mL of ammonium hydroxide solution per liter)

출처 및 근거

ORD 기록
ord-5b235e9df7744ec3991a5655baa4c94f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088788B2

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