Water → 2-(3-ethynyl-quinolin-6-yloxy)-N-[1-(methoxyimino-methyl)-cyclobutyl]-2-methylsulfanyl-acetamide

HRID 1892057노트

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HRID 1892057 반응식
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]1([CH:22]=O)[CH2:21][CH2:20][CH2:19]1)=[O:16])=[CH:8][CH:7]=2)#[CH:2].C([O-])(=O)C.[Na+].Cl.[CH3:32][O:33][NH2:34].O>C(O)C>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13][CH:14]([S:24][CH3:25])[C:15]([NH:17][C:18]1([CH:22]=[N:34][O:33][CH3:32])[CH2:19][CH2:20][CH2:21]1)=[O:16])=[CH:8][CH:7]=2)#[CH:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 595654712-(3-ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide

생성물 1

HCID 866480232-(3-ethynyl-quinolin-6-yloxy)-N-[1-(methoxyimino-methyl)-cyclobutyl]-2-methylsulfanyl-acetamide수율 81.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
65 °C

실험 절차

To a solution of 2-(3-Ethynyl-quinolin-6-yloxy)-N-(1-formyl-cyclobutyl)-2-methylsulfanyl-acetamide (125 mg) in ethanol (10 ml) was added sodium acetate (50 mg) and O-methyl hydroxylamine hydrochloride (44 mg), at room temperature. The mixture was heated to 65° C. during 1 hour. After cooling to room temperature the mixture was poured into water and extracted with ethyl acetate (2×10 ml). The organic phase was washed with sat. aq NaCl solution, dried over anhydrous sodium sulphate, filtered and evaporated under vacuum. Purification by flash chromatography (ethyl acetate/cyclohexane, 1/1) gave 2-(3-ethynyl-quinolin-6-yloxy)-N-[1-(methoxyimino-methyl)-cyclobutyl]-2-methylsulfanyl-acetamide (110 mg) as a yellow oil.

후처리

  1. customat room temperature
  2. temperatureAfter cooling to room temperature the mixture
  3. extractionextracted with ethyl acetate (2×10 ml)
  4. washThe organic phase was washed with sat. aq NaCl solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customevaporated under vacuum
  8. customPurification by flash chromatography (ethyl acetate/cyclohexane, 1/1)

출처 및 근거

ORD 기록
ord-1d483cba6ab944b49c224a0aaa9640fb
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507509B2

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