Pyridine → (R)-2-(6-Cyclopropyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 418503Notes

Reaction equation

HRID 418503 reaction equation
[CH:1]1([C:4]2[C:5]([N+:19]([O-:21])=[O:20])=[C:6]3[C:11](=[CH:12][CH:13]=2)[C:10](=[O:14])[N:9]([C@H:15]([CH3:18])[CH2:16][OH:17])[CH:8]=[CH:7]3)[CH2:3][CH2:2]1.[C:22](OC(=O)C)(=[O:24])[CH3:23].N1C=CC=CC=1.C(Cl)Cl>>[C:22]([O:17][CH2:16][C@H:15]([N:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][CH:13]=[C:4]([CH:1]3[CH2:3][CH2:2]3)[C:5]=2[N+:19]([O-:21])=[O:20])[C:10]1=[O:14])[CH3:18])(=[O:24])[CH3:23]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 59515744(R)-6-cyclopropyl-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one

Product 1

HCID 59515735(R)-2-(6-Cyclopropyl-5-nitro-1-oxoisoquinolin-2(1H)-yl)propyl acetate

Procedure

A round bottom flask was charged with (R)-6-cyclopropyl-2-(1-hydroxypropan-2-yl)-5-nitroisoquinolin-1(2H)-one (30 mg, 0.0001 mol), acetic anhydride (0.015 mL, 0.00016 mol), pyridine (0.015 mL, 0.00019 mol) and methylene chloride (4 mL, 0.06 mol), and was stirred at room temperature overnight. The solvent was removed under reduced pressure and the product was taken onto the next step without purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe product was taken onto the next step without purification

Sources & evidence

ORD record
ord-652f5ca6049541a4b469f569e223fafd
Source dataset
uspto-grants-2012_01
Patent number
US08093265B2

Reaction notes

Loading…