Cyclopentylamine → HCID 18326384, compound

HRID 1250580Notes

Reaction equation

HRID 1250580 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].CN1CCN(C)C1=O.P(Cl)(Cl)([Cl:26])=O.C(N(CC)CC)C.[CH:36]1([NH2:41])[CH2:40][CH2:39][CH2:38][CH2:37]1>O>[Cl:26][C:9]1[N:8]=[C:7]([NH:41][CH:36]2[CH2:40][CH2:39][CH2:38][CH2:37]2)[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

Participants

7

Reactant 5

HCID 2906CyclopentylamineHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

Product 1

HCID 18326384HCID 18326384, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 300 mg (1.45 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione were added 1 ml of 1,3-dimethyl-2-imidazolidinone and 1.23 g (8.05 mmol) of phosphorus oxychloride, and the resulting mixture was subjected to heating under reflux for 3 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 3 ml of acetonitrile, followed by addition of 4.05 ml (29.00 mmol) of triethylamine and 0.89 ml (8.70 mmol) of cyclopentylamine and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 152 mg (yield: 35.9%) of the title compound.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 3 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 3 ml of acetonitrile
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled off
  9. customthe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-51624ec3ae164dddb4035433328026f9
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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