Water → 4-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamide

HRID 498086노트

반응식

HRID 498086 반응식
[C:1]([N:5]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[NH2:31][C:32]1[CH:41]=[CH:40][C:39]([OH:42])=[C:38]2[C:33]=1[CH:34]=[CH:35][CH:36]=[N:37]2.O>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:1]([N:5]([C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:31][C:32]2[CH:41]=[CH:40][C:39]([OH:42])=[C:38]3[C:33]=2[CH:34]=[CH:35][CH:36]=[N:37]3)=[O:19])=[CH:21][CH:22]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:8])[CH3:9])([CH3:4])([CH3:2])[CH3:3]

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 113707224-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-benzoic acidHCID 122537915-Aminoquinolin-8-ol hydrochloride

생성물 1

HCID 223207184-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamide수율 35.2%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 0.15 g (0.464 mmol) of compound 2 in CH2Cl2 (2 mL) were added 0.11 g (0.561 mmol) of 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride, 0.03 g (0.232 mmol) of 4-dimethylaminopyridine, 2 mL of triethylamine, and 0.16 g (0.695 mmol) of 5-amino-8-hydroxyquinoline HCl salt. After stirring for 24 hours at room temperature, H2O and ethyl acetate were added. The organic layer was separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, Hex:EtOAc=1:1) to give 0.076 g of compound 9 in 35% yield.

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography (silica, Hex:EtOAc=1:1)

출처 및 근거

ORD 기록
ord-2f8f8a81da3d4b2c91344163eb668f07
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949654B2

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