Triethylamine → HCID 67052453, compound

HRID 598036

Reaction equation

HRID 598036 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.C(N(CC)CC)C.[NH2:23][CH2:24][C:25]1([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26]1>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:23][CH2:24][C:25]3([OH:30])[CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:7]([N+:12]([O-:14])=[O:13])[CH:8]=[N:9]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130512021-(Aminomethyl)cyclopentan-1-olHCID 574578377-Bromo-4-chloro-3-nitro[1,5]naphthyridine

Product 1

HCID 67052453HCID 67052453, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 7-bromo-4-chloro-3-nitro[1,5]naphthyridine (54.42 g, 188.6 mmol) in chloroform (820 mL) was cooled to 0° C., and triethylamine (105 mL, 755 mmol) was added. A solution of 1-(aminomethyl)cyclopentanol (28.25 g, 245.2 mmol) in chloroform (272 mL) was added slowly over a period of 15 minutes. The reaction was allowed to warm to room temperature and stirred for 30 minutes. The solution was washed sequentially with water (500 mL) and saturated aqueous sodium bicarbonate (750 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 1-{[(7-bromo-3-nitro[1,5]naphthyridin-4-yl)amino]methyl}cyclopentanol.

Workup

  1. temperatureto warm to room temperature
  2. washThe solution was washed sequentially with water (500 mL) and saturated aqueous sodium bicarbonate (750 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3aa6b0b83bb485ca8fb2bfacae7a3f6
Source dataset
uspto-grants-2011_03
Patent number
US07897609B2

Linked notes

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