3-Fluoro-5-nitroaniline → HCID 67389955, compound

HRID 913284Notes

Reaction equation

HRID 913284 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10](Cl)[N:9]=2)[N:5]=[CH:4][N:3]=1.[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1)[NH2:19].[CH3:26][O:27][CH2:28][C@@H:29]([NH2:31])[CH3:30]>O1CCCC1>[F:15][C:16]1[CH:17]=[C:18]([NH:19][C:2]2[N:7]=[C:6]([C:8]3[CH:13]=[CH:12][N:11]=[C:10]([NH:31][C@@H:29]([CH3:30])[CH2:28][O:27][CH3:26])[N:9]=3)[N:5]=[CH:4][N:3]=2)[CH:20]=[C:21]([N+:23]([O-:25])=[O:24])[CH:22]=1

Participants

5

Reactant 3

HCID 754003-Fluoro-5-nitroanilineHCID 70215362-Propanamine, 1-methoxy-, (2S)-HCID 86646773HCID 86646773, compound2×

Product 1

HCID 67389955HCID 67389955, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-chloro-4-(2-chloro-4-pyrimidinyl)-1,3,5-triazine (i.e., the product of Example 1, Step B) (68 mg, 0.30 mmol) in tetrahydrofuran (2.0 mL) was added 3-fluoro-5-nitroaniline (72 mg, 0.46 mmol), and the resulting mixture was stirred at 50° C. for 1 h to form a yellow suspension. To this suspension was added (S)-1-methoxy-2-propylamine (0.2 mL), and the resulting mixture was refluxed for 3 h. The solution was concentrated and purified using column chromatography on silica gel eluted with 70% ethyl acetate in hexanes to give 93 mg of the title compound as yellow solid.

Workup

  1. customto form a yellow suspension
  2. temperaturethe resulting mixture was refluxed for 3 h
  3. concentrationThe solution was concentrated
  4. custompurified
  5. washeluted with 70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-1c7fd9d9aa624ae9b0f50dc6fd3e6185
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

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