Potassium Carbonate → tert-butyl 5-(2-(4-fluorophenyl)-6-(N'-hydroxycarbamimidoyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

HRID 927283Notes

Reaction equation

HRID 927283 reaction equation
Cl.[NH2:2][OH:3].[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)[C:10]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:9]2)#[N:5].C([O-])([O-])=O.[K+].[K+]>CO.ClCCl>[F:23][C:20]1[CH:21]=[CH:22][C:17]([N:11]2[C:10]([CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:9][C:8]3[C:13](=[CH:14][CH:15]=[C:6]([C:4](=[N:2][OH:3])[NH2:5])[CH:7]=3)[C:12]2=[O:16])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 118558143Tert-butyl 5-(6-cyano-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

Product 1

HCID 90095090tert-butyl 5-(2-(4-fluorophenyl)-6-(N'-hydroxycarbamimidoyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoateYield 100.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Hydroxylamine hydrochloride (183 mg, 2.64 mmol) was added to a stirred, room temperature mixture of tert-butyl 5-(6-cyano-2-(4-fluorophenyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (185 mg, 0.440 mmol) and K2CO3 (365 mg, 2.64 mmol) in MeOH (20 mL) and the mixture was stirred at room temperature for overnight. The mixture was diluted with dichloromethane (60 mL), washed with aqueous ammonium chloride (saturated, 1×20 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure to give tert-butyl 5-(2-(4-fluorophenyl)-6-(N′-hydroxycarbamimidoyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (200 mg, 0.441 mmol) as an off white solid.

Workup

  1. washwashed with aqueous ammonium chloride (saturated, 1×20 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-adc6e820905c4dde885de98843bed77f
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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