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

HRID 1376152Notes

Reaction equation

HRID 1376152 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-08be3326669a49aba80cfc5f7732c119
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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