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

HRID 1161280Notes

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

Reactant 4

HCID 1049Pyridine

HCID 6344Dichloromethane

HCID 7918Acetic Anhydride

HCID 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 the reaction stirred at room temperature over night. The solvent was then removed and the product was taken to the next step without purification. MS m/z=331.5 (M+H).

Workup

customThe solvent was then removed
customthe product was taken to the next step without purification

Sources & evidence

ORD record: ord-92c436b097204fb2a4aaef58b1e41af7
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816371B2

Reaction notes

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