Methanol → HCID 67521556, 화합물

HRID 1924031노트

반응식

HRID 1924031 반응식
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][CH2:16][OH:17])=[N:11][CH:10]=[CH:9][CH:8]=2)([O-:3])=[O:2].[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].CO>N1C=CC=CC=1.C(OCC)(=O)C>[Si:18]([O:17][CH2:16][CH2:15][NH:14][C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][N:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

참가 물질

6

반응물 3

HCID 887MethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 59026691HCID 59026691, 화합물

생성물 1

HCID 67521556HCID 67521556, 화합물수율 77.1%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 2-[(3-nitro[1,5]naphthyridin-4-yl)amino]ethanol (6.34 g, 27.1 mmol) dissolved in 25 mL of pyridine was treated with tert-butyldimethylsilyl chloride (4.50 g, 29.8 mmol) and N,N-dimethylaminopyridine (331 mg, 2.71 mmol) and the mixture was stirred under N2. After 3 hours, the reaction mixture was treated with 10 mL of methanol and then concentrated to give a yellow solid. The resulting solid was dissolved in 100 mL of ethyl acetate and washed with H2O (3×50 mL) and brine. The organic portion was dried over Na2SO4, filtered and concentrated under reduced pressure to give a yellow powder. Crystallization from 50 mL of 1:1 hexane/ethyl acetate gave 7.28 g of N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-3-nitro[1,5]naphthyridin-4-amine as a yellow solid.

후처리

  1. concentrationconcentrated
  2. customto give a yellow solid
  3. washwashed with H2O (3×50 mL) and brine
  4. dry with materialThe organic portion was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto give a yellow powder
  8. customCrystallization from 50 mL of 1:1 hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-8f5cd10cce7743ae89dd28f72ce45eba
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178539B2

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