Water → 4-Allylamino-6-nitro-2-[2-(piperidinocarbonyl)ethylamino]quinazoline

HRID 1250604Notes

Reaction equation

HRID 1250604 reaction equation
[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7](Cl)[N:6]=1)[CH:2]=[CH2:3].Cl.[N:20]1([C:26]([CH2:28][CH2:29][NH2:30])=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C.O>C(#N)C>[CH2:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=2)[N:8]=[C:7]([NH:30][CH2:29][CH2:28][C:26]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:27])[N:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 177503443-Amino-1-(piperidin-1-yl)propan-1-one hydrochlorideHCID 183264874-Allylamino-2-chloro-6-nitroquinazoline

Product 1

HCID 183265474-Allylamino-6-nitro-2-[2-(piperidinocarbonyl)ethylamino]quinazolineYield 87.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

150 mg (0.57 mmol) of 4-allylamino-2-chloro-6-nitroquinazoline was dissolved in 10 ml of acetonitrile, and then 220 mg (1.14 mmol) of 2-piperidinocarbonylethylamine hydrochloride and 0.40 ml (2.85 mmol) of triethylamine were added thereto, followed by heating under reflux overnight. 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 191 mg (87.7%) of the title compound.

Workup

  1. temperatureby heating
  2. temperatureunder reflux overnight
  3. extractionfollowed by extraction with ethyl acetate
  4. washwashing with brine
  5. dry with materialdrying over anhydrous sodium sulfate
  6. distillationAfter the solvent was distilled off
  7. customthe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-d13ea15565794d88ab9a2961f944eb54
Source dataset
uspto-grants-2002_01
Patent number
US06339089B2

Reaction notes

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