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

HRID 81904Notes

Reaction equation

HRID 81904 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](Cl)=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[N:11][CH:10]=1.[NH2:23][CH2:24][C:25]([CH3:28])([OH:27])[CH3:26]>ClCCl>[Br:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:23][CH2:24][C:25]([CH3:28])([OH:27])[CH3:26])=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 951022-Propanol, 1-amino-2-methyl-HCID 574578377-Bromo-4-chloro-3-nitro[1,5]naphthyridine

Product 1

HCID 670524611-[(7-Bromo-3-nitro[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-olYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (35.95 mL, 257.9 mmol) was added to a suspension of 7-bromo-4-chloro-3-nitro[1,5]naphthyridine (49.6 g, 172 mmol) in dichloromethane (500 mL). 1-Amino-2-methylpropan-2-ol (16.86 g, 189 mmol) was added dropwise. The reaction mixture was stirred at ambient temperature for 16 hours and then concentrated under reduced pressure. The residue was triturated with water and stirred for 1 hour. The precipitated solid was isolated by filtration, washed with water, and dried. This material was suspended in diethyl ether (400 mL), sonicated, isolated by filtration, and then dried in a vacuum oven at 40° C. for 16 hours to provide 58.1 g of 1-[(7-bromo-3-nitro[1,5]naphthyridin-4-yl)amino]-2-methylpropan-2-ol as a yellow solid, mp 189-190° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was triturated with water
  3. stirringstirred for 1 hour
  4. customThe precipitated solid was isolated by filtration
  5. washwashed with water
  6. customdried
  7. customsonicated
  8. customisolated by filtration
  9. customdried in a vacuum oven at 40° C. for 16 hours

Sources & evidence

ORD record
ord-8dfa7cd7c2514701ae825034146ec50d
Source dataset
uspto-grants-2014_09
Patent number
US08846710B2

Reaction notes

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