Water → N-(2-fluoro-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine

HRID 81932Notes

Reaction equation

HRID 81932 reaction equation
Cl.[F:2][C:3]([CH3:7])([CH3:6])[CH2:4][NH2:5].C(N(CC)CC)C.Cl[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][N:24]=2)[N:19]=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27].O>C(Cl)Cl>[F:2][C:3]([CH3:7])([CH3:6])[CH2:4][NH:5][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][N:24]=2)[N:19]=[CH:18][C:17]=1[N+:26]([O-:28])=[O:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 131227874-Chloro-3-nitro-1,5-naphthyridineHCID 552896302-Fluoro-2-methylpropan-1-amine hydrochloride

Product 1

HCID 68934906N-(2-fluoro-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amineYield 100.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-2-methylpropan-1-amine hydrochloride (4.02 g, 31.4 mmol) was dissolved in 80 mL of dry CH2Cl2. Triethylamine (13.1 mL, 94.2 mmol) and 4-chloro-3-nitro[1,5]naphthyridine (6.56 g, 31.4 mmol) were then added and the reaction was stirred under N2 for 2 days. The reaction mixture was then concentrated under reduced pressure to give a dark-yellow solid. The solid was treated with 200 mL of H2O and the mixture was heated to reflux with rapid stirring. The mixture was cooled and the yellow solid was isolated by filtration. The material was washed with H2O and the dried under vacuum to give N-(2-fluoro-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine (8.36 g) as a yellow powder.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customto give a dark-yellow solid
  3. temperaturethe mixture was heated
  4. temperatureto reflux with rapid stirring
  5. temperatureThe mixture was cooled
  6. customthe yellow solid was isolated by filtration
  7. washThe material was washed with H2O
  8. customthe dried under vacuum

Sources & evidence

ORD record
ord-1c273022fbee4b17b9446102647a86bb
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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