Hydrochloric Acid → HCID 68656226, compound

HRID 1402767Notes

Reaction equation

HRID 1402767 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:8](=[O:22])[N:9]2[CH2:12][CH2:13][NH:14]C(=O)OC(C)(C)C)=[CH:4][CH:3]=1.[ClH:27]>O1CCOCC1>[ClH:27].[NH2:14][CH2:13][CH2:12][N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[C:2]([Br:1])[CH:11]=2)[N:6]=[C:7]([C:23]([CH3:25])([CH3:24])[CH3:26])[C:8]1=[O:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59314073HCID 59314073, compound

Product 1

HCID 68656226HCID 68656226, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-butyl 2-(7-bromo-3-tert-butyl-2-oxoquinoxalin-1(2H)-yl)ethylcarbamate (360 mg, 0.85 mmol), the compound of formula (a), prepared as described in Example 3B, was dissolved in dioxane (1 mL) and reacted with 4N hydrochloric acid in dioxane (1 mL) at room temperature for 3 days. The solution was concentrated to provide 1-(2-aminoethyl)-7-bromo-3-tert-butylquinoxalin-2(1H)-one hydrochloride as a tan solid. This solid was dissolved in chloroform (8 mL), and acetoxyacetyl chloride (0.107 mL) and triethylamine (0.5 mL) were added in small portions over a period of 3 hours. The reaction mixture was then concentrated under reduced pressure, and the resulting 2-(2-(7-bromo-3-tert-butyl-2-oxoquinoxalin-1(2H)-yl)ethylamino)-2-oxoethyl acetate (b) was crystallized from methanol, then taken up in ethyl acetate (10 mL) and washed 3 times with water, then brine, dried over sodium sulfate, and concentrated under reduced pressure to provide 280 mg of 2-(2-(7-bromo-3-tert-butyl-2-oxoquinoxalin-1(2H)-yl)ethylamino)-2-oxoethyl acetate as an oil that crystallized upon standing into a white solid.

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-dc436b4227ec453bbd9f36162404b3f1
Source dataset
uspto-grants-2014_12
Patent number
US08912190B2

Reaction notes

Loading…