Hydrochloric Acid → 2-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-2-hydroxy-1-methyl-ethyl)-2-methylsulfanyl acetamide

HRID 1892044

반응식

HRID 1892044 반응식
ON1C2N=CC=CC=2N=N1.CN(C)CCCN=C=NCC.Cl.[Br:23][C:24]1[CH:25]=[N:26][C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([O:34][CH:35]([S:39][CH3:40])[C:36]([OH:38])=O)=[CH:29][CH:28]=2.[NH2:41][C:42]([CH3:47])([CH2:45][OH:46])[C:43]#[N:44]>CN(C=O)C.[Cl-].[Na+].O.C(OCC)(=O)C.C(N(CC)CC)C>[Br:23][C:24]1[CH:25]=[N:26][C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([O:34][CH:35]([S:39][CH3:40])[C:36]([NH:41][C:42]([C:43]#[N:44])([CH3:47])[CH2:45][OH:46])=[O:38])=[CH:29][CH:28]=2

참가 물질

10

반응물 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 144057522-Amino-3-hydroxy-2-methylpropanenitrileHCID 66717844(3-Bromo-quinolin-6-yloxy)-methylsulfanyl-acetic acid

생성물 1

HCID 667174052-(3-Bromo-quinolin-6-yloxy)-N-(1-cyano-2-hydroxy-1-methyl-ethyl)-2-methylsulfanyl acetamide수율 65.4%

시약·촉매·용매 4

HCID 6228Dimethylformamide용매2회HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

0.86 ml of Triethylamine, 0.672 g of 1-hydroxy-7-azabenzotriazole and 0.946 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide.HCl were added at R.T. to a suspension of 1.35 g of (3-bromo-quinolin-6-yloxy)-methylsulfanyl-acetic acid in 11 ml of dry DMF. To this suspension, 0.494 g of 2-amino-3-hydroxy-2-methyl-propionitrile dissolved in 2 ml of dry DMF were added dropwise. The reaction mixture was stirred 16 hrs at R.T and then poured onto a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted thrice with ethyl acetate. The organic layers were combined, washed once with brine and then dried over sodium sulphate. After filtration and concentration under reduced pressure 1.886 g of a crude mixture were isolated as a dark orange oil. The crude mixture was purified by flash chromatography on silica gel (hexane/ethyl acetate) to give 1.103 g of 2-(3-bromo-quinolin-6-yloxy)-N-(1-cyano-2-hydroxy-1-methyl-ethyl)-2-methylsulfanyl acetamide in mixture with 3-(3-bromo-quinolin-6-yl)-2-methylsulfanyl-propionic acid 2-[2-(3-bromo-quinolin-6-yloxy)-2-methylsulfanyl-acetylamino]-2-cyano-2-methyl-ethyl ester resulting from the homo coupling process.

후처리

  1. additionwere added dropwise
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted thrice with ethyl acetate
  4. washwashed once with brine
  5. dry with materialdried over sodium sulphate
  6. filtrationAfter filtration and concentration under reduced pressure 1.886 g of a crude mixture
  7. customwere isolated as a dark orange oil
  8. customThe crude mixture was purified by flash chromatography on silica gel (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-52603565c39e47119937549e169673ea
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507509B2

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