Tetrahydrofuran → N-[1-[(2Z)-2-amino-2-hydroxyiminoethyl]-2-oxo-3,4-dihydroquinolin-3-yl]-5-chloro-1H-indole-2-carboxamide

HRID 1376152노트

반응식

HRID 1376152 반응식
Cl.[NH2:2][OH:3].C[O-].[Na+].C1COCC1.[Cl:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]([C:22]([NH:24][CH:25]1[CH2:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]([CH2:35][C:36]#[N:37])[C:26]1=[O:38])=[O:23])=[CH:16]2>CO>[NH2:37]/[C:36](=[N:2]\[OH:3])/[CH2:35][N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:34][CH:25]([NH:24][C:22]([C:17]2[NH:18][C:19]3[C:15]([CH:16]=2)=[CH:14][C:13]([Cl:12])=[CH:21][CH:20]=3)=[O:23])[C:26]1=[O:38]

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 443297Hydroxyamine hydrochlorideHCID 100452425-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamideHCID 10942334Sodium Methoxide

생성물 1

HCID 10237861N-[1-[(2Z)-2-amino-2-hydroxyiminoethyl]-2-oxo-3,4-dihydroquinolin-3-yl]-5-chloro-1H-indole-2-carboxamide수율 44%

시약·촉매·용매 1

HCID 887Methanol용매3회

실험 절차

A solution hydroxylamine hydrochloride (147 mg, 2.11 mmol) in MeOH (4 mL) was added to a solution of sodium methoxide in methanol (0.5 M, 4.2 mL, 2.1 mmol) that had been further diluted with methanol (4 mL). After stirring for 10 minutes, THF (4 mL) was added followed by portionwise addition of 5-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide (Method 11, 400 mg, 1.06 mmol). The reaction mixture was stirred at ambient temperature for 18 h, partitioned between EtOAc (80 mL) and diluted brine (80 mL), filtered and the layers of the filtrate separated. The organic phase was dried (Na2SO4) and the volatiles removed under reduced pressure to give the title material (191 mg, 44%) as a yellow solid.

후처리

  1. stirringThe reaction mixture was stirred at ambient temperature for 18 h
  2. custompartitioned between EtOAc (80 mL) and diluted brine (80 mL)
  3. filtrationfiltered
  4. customthe layers of the filtrate separated
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customthe volatiles removed under reduced pressure

출처 및 근거

ORD 기록
ord-08be3326669a49aba80cfc5f7732c119
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07169927B2

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