Trichloroacetyl isocyanate → Ethyl 8-[(aminocarbonyl)amino]-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 44602

Reaction equation

HRID 44602 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.ClC(Cl)(Cl)[C:23]([N:25]=C=O)=[O:24]>N1C=CC=CC=1>[NH2:25][C:23]([NH:1][C:2]1[N:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1)=[O:24]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 57444093Ethyl 8-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

Product 1

HCID 68932803Ethyl 8-[(aminocarbonyl)amino]-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylateYield 34.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.00 g (3.7 mmol) of ethyl 8-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate were dissolved in 50 mL of pyridine and 1 mL (8.0 mmol) of trichloroacetylisocyanate were added. The mixture was stirred overnight at room temperature. The solvent was then evaporated under reduced pressure and the residue was treated with 50 mL of methanol. After 2 hours under stirring the solvent was removed, the residue redissolved with dichloromethane and washed with a diluted solution of ammonium hydrate. After drying over anhydrous Na2SO4 the organic layer was evaporated to dryness and the residue purified by chromatography on a silica gel column (eluant: dichloromethane/acetone 4/1) leading 0.40 g (34% yield) of the title compound.

Workup

  1. customThe solvent was then evaporated under reduced pressure
  2. additionthe residue was treated with 50 mL of methanol
  3. stirringAfter 2 hours under stirring the solvent
  4. customwas removed
  5. dissolutionthe residue redissolved with dichloromethane
  6. washwashed with a diluted solution of ammonium hydrate
  7. dry with materialAfter drying over anhydrous Na2SO4 the organic layer
  8. customwas evaporated to dryness
  9. customthe residue purified by chromatography on a silica gel column (eluant: dichloromethane/acetone 4/1)

Sources & evidence

ORD record
ord-cbb790befb01415a839ffc9b7991561d
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Linked notes

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