Water → HCID 67521014, compound

HRID 1924037Notes

Reaction equation

HRID 1924037 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][N:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(N(CC)CC)C.[NH2:22][C@H:23]([CH3:26])[CH2:24][OH:25].O>C(Cl)Cl>[N+:12]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:22][C@H:23]([CH3:26])[CH2:24][OH:25])=[N:10][CH:9]=[CH:8][CH:7]=2)([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 80308(R)-(-)-2-Amino-1-propanolHCID 131227874-Chloro-3-nitro-1,5-naphthyridine

Product 1

HCID 67521014HCID 67521014, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-chloro-3-nitro[1,5]naphthyridine (6.30 g, 30.1 mmol) dissolved in 150 mL of CH2Cl2 was treated with triethylamine (8.35 mL, 60.0 mmol) and (R)-2-aminopropanol (2.76 mL, 35.5 mmol) and the mixture was stirred under N2. After 18 hours, the reaction mixture was concentrated to give a yellow solid. The yellow solid was combined with 150 mL of H2O and the suspension was heated to reflux, with stirring, for 20 minutes. The mixture was cooled in an ice bath and the resulting yellow solid was isolated by filtration. The solid washed with cold H2O and two 50 mL-portions of Et2O and then dried with suction to give (2R)-2-[(3-nitro[1,5]naphthyridin-4-yl)amino]propan-1-ol (7.10 g) as a yellow powder.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customto give a yellow solid
  3. temperaturethe suspension was heated
  4. temperatureto reflux
  5. stirringwith stirring, for 20 minutes
  6. temperatureThe mixture was cooled in an ice bath
  7. customthe resulting yellow solid was isolated by filtration
  8. washThe solid washed with cold H2O and two 50 mL-portions of Et2O
  9. customdried with suction

Sources & evidence

ORD record
ord-53bc09efd2244a0db89915291c9c54fb
Source dataset
uspto-grants-2012_05
Patent number
US08178539B2

Reaction notes

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