2-Propanol, 1-amino-2-methyl- → 1-[(7-Bromo-3-nitro[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol

HRID 909359Notes

Reaction equation

[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[N:4][CH:3]=1.[NH2:16][CH2:17][C:18]([CH3:21])([OH:20])[CH3:19]>ClCCl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:16][CH2:17][C:18]([CH3:21])([OH:20])[CH3:19])=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[N:4][CH:3]=1

Participants

Conditions

Temperature: 10 °C

Procedure

A mixture of 7-bromo-4-chloro-3-nitro[1,5]naphthyridine (92.5 g, 321 mmol) and dichloromethane (1.5 L) was cooled to 10° C. 1-Amino-2-methylpropan-2-ol (63.01 g, 707 mmol) was added dropwise over a period of 30 minutes; during the addition, the reaction temperature did not rise above 13° C. The reaction mixture was allowed to slowly warm to room temperature and stirred overnight. The solvent was removed under reduced pressure, and the solid residue was mixed with water (200 mL). The solid was isolated by filtration, washed with water (2×200 mL), and dried in a vacuum oven overnight at 35° C. to provide 1-[(7-bromo-3-nitro[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol.

Workup

additionduring the addition
customdid not rise above 13° C
temperatureto slowly warm to room temperature
customThe solvent was removed under reduced pressure
additionthe solid residue was mixed with water (200 mL)
customThe solid was isolated by filtration
washwashed with water (2×200 mL)
customdried in a vacuum oven overnight at 35° C.

Sources & evidence

ORD record: ord-0233111dea2f40cb9799301eb806888f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017779B2

Reaction notes

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