Sodium Hydroxide → HCID 19902144, compound

HRID 2372720Notes

Reaction equation

HRID 2372720 reaction equation
[N:1]1[CH2:2][CH2:3][N:4]2[C:13]=1[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]1[CH:14]=[N:15][C:16]([C:17](OCC)=[O:18])=[C:5]21.[CH:22]1([C:25](=[N:27]O)[NH2:26])[CH2:24][CH2:23]1.[H-].[Na+].[OH-].[Na+]>CN(C=O)C.O.C(O)C.ClCCl>[CH:22]1([C:25]2[N:27]=[C:17]([C:16]3[N:15]=[CH:14][N:6]4[C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=5[C:13]5=[N:1][CH2:2][CH2:3][N:4]5[C:5]=34)[O:18][N:26]=2)[CH2:24][CH2:23]1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydride2×HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 19902197HCID 19902197, compound

Product 1

HCID 19902144HCID 19902144, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2,3-dihydrodiimidazo[1,5-a:1',2'-c]quinazoline-5-carboxylate (1.0 g, 3.5 mmol), cyclopropancarboxamide oxime (1.0 g, 10 mmol), crushed 4 Å molecular sieves (1 g), and sodium hydride (approx. 10 mg of a 55% oil dispersion) in dry DMF was stirred at room temperature for one week. Additional catalytic amounts of NaH were added regularly during the reaction (4×10 mg). Then dichloromethane (50 ml) was added, and the insoluble material was removed by filtration through celite. The filtrate was evaporated in vacuo, the residue triturated with water (50 ml), and the resulting precipitate was filtered off. The crude product thus obtained was heated at reflux for 10 min. in a mixture of water (10 ml), ethanol (5 ml), and 4M sodium hydroxide (2 ml). Then the mixture was cooled to room temperature and the precipitate was filtered off and dried to give the title compound, m.p. 235°-238° C. (Compound 2 ).

Workup

  1. customthe insoluble material was removed by filtration through celite
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue triturated with water (50 ml)
  4. filtrationthe resulting precipitate was filtered off
  5. customThe crude product thus obtained
  6. temperaturewas heated
  7. temperatureThen the mixture was cooled to room temperature
  8. filtrationthe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-10ef66bde4544c498933781c2de9a6c1
Source dataset
uspto-grants-1992_03
Patent number
US05100895

Reaction notes

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