Methanol → tert-Butyl methyl(2-(6-methyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)ethyl)carbamate

HRID 418526Notes

Reaction equation

HRID 418526 reaction equation
[CH3:1][C:2]1[C:3]([N+:13]([O-:15])=[O:14])=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])O[CH:6]=[CH:5]2.[NH2:16][CH2:17][CH2:18][N:19]([CH3:27])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23].C(N(CC)CC)C.CO>>[CH3:27][N:19]([CH2:18][CH2:17][N:16]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[C:3]=2[N+:13]([O-:15])=[O:14])[C:8]1=[O:12])[C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 2756424N-Boc-N-methylethylenediamineHCID 595157846-Methyl-5-nitro-1H-isochromen-1-one

Product 1

HCID 66649171tert-Butyl methyl(2-(6-methyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)ethyl)carbamate

Conditions

Temperature
100 °C

Procedure

A microwave vial was charged with 6-methyl-5-nitro-1H-isochromen-1-one (270 mg, 0.0012 mol), tert-butyl 2-aminoethylmethylcarbamate (400 mg, 0.002 mol), triethylamine (0.6 mL, 0.005 mol) and methanol (5 mL, 0.1 mol) and the reaction was heated at 100° C. for 1.5 hours. The solvents were removed under reduced pressure and the residue was purified by flash chromatography to afford the desired product as a brown oil.

Workup

  1. customThe solvents were removed under reduced pressure
  2. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7ebdfb346b064c1b806394e2f869550b
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

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