Water → HCID 67052462, compound

HRID 598046Notes

Reaction equation

HRID 598046 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.Cl.[F:24][C:25]([CH3:29])([CH3:28])[CH2:26][NH2:27].O>CN(C=O)C>[Br:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:27][CH2:26][C:25]([F:24])([CH3:29])[CH3:28])=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[N:16]2)=[N:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 552896302-Fluoro-2-methylpropan-1-amine hydrochlorideHCID 574578377-Bromo-4-chloro-3-nitro[1,5]naphthyridine

Product 1

HCID 67052462HCID 67052462, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Triethylamine (17.3 g, 171 mmol) was added to a suspension of 7-bromo-4-chloro-3-nitro[1,5]naphthyridine (52.2 mmol) in DMF (50 mL), and then a solution of 2-fluoro-2-methylpropan-1-amine hydrochloride (5.46 g, 42.8 mmol) in DMF (25 mL) was added dropwise over a period of ten minutes. The reaction mixture was stirred at room temperature for 14.5 hours, and water (500 mL) was added. The resulting mixture was stirred for one hour. A solid was present and was isolated by filtration, washed with water, and dried overnight in a vacuum oven at 65° C. to provide 14.7 g of 7-bromo-N-(2-fluoro-2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine as a reddish-brown solid.

Workup

  1. stirringThe resulting mixture was stirred for one hour
  2. customwas isolated by filtration
  3. washwashed with water
  4. customdried overnight in a vacuum oven at 65° C.

Sources & evidence

ORD record
ord-61ead96cd65d4d57a4059e194815e63c
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Reaction notes

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