Ethanol → N-[2-[(2R)-1-aminopropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamide

HRID 418536Notes

Reaction equation

HRID 418536 reaction equation
[N:1]([CH2:4][C@H:5]([N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:32])[C:13]=2[NH:17][C:18](=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[C:22]([F:30])[CH:21]=2)[C:8]1=[O:33])[CH3:6])=[N+]=[N-].C(O)C.[Cl-].[NH4+].O>[Fe]>[NH2:1][CH2:4][C@H:5]([N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH3:32])[C:13]=2[NH:17][C:18](=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:28])([F:29])[F:27])=[C:22]([F:30])[CH:21]=2)[C:8]1=[O:33])[CH3:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 59845723(R)-N-(2-(1-azidopropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamide

Product 1

HCID 25014313N-[2-[(2R)-1-aminopropan-2-yl]-6-methyl-1-oxoisoquinolin-5-yl]-2-[3-fluoro-4-(trifluoromethyl)phenyl]acetamideYield 53.3%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

A solution of (R)—N-(2-(1-azidopropan-2-yl)-6-methyl-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetamide (0.6 g, 0.001 mol) in ethanol (50 mL, 0.8 mol) was heated at 85° C. A solution of ammonium chloride (0.6 g, 0.01 mol) in water (15 mL, 0.83 mol) was added followed by iron powder (0.6 g, 0.01 mol). The mixture was stirred at the same temperature for 3 hours and poured onto dichloromethane (200 mL) and extracted. The residue was purified by reverse phase HPLC to afford the desired product as a white solid (232 mg, yield 50%).

Workup

  1. additionpoured onto dichloromethane (200 mL)
  2. extractionextracted
  3. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-fd821094142f4ced8bc1ca00cef29173
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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