Acetic Acid → HCID 18953464, compound

HRID 1491617Notes

Reaction equation

HRID 1491617 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]3[CH:17]=[N:18][C:19]([C:20](OCC)=[O:21])=[C:9]3[N:8]=2)[CH2:3][CH2:2]1.[CH:25]1([C:28](=[N:30]O)[NH2:29])[CH2:27][CH2:26]1.[H-].[Na+].C(O)(=O)C>CN(C=O)C.ClCCl>[CH:25]1([C:28]2[N:30]=[C:20]([C:19]3[N:18]=[CH:17][N:10]4[C:11]5[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=5)[C:7]([N:4]5[CH2:3][CH2:2][O:1][CH2:6][CH2:5]5)=[N:8][C:9]=34)[O:21][N:29]=2)[CH2:27][CH2:26]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 18953495HCID 18953495, compound

Product 1

HCID 18953464HCID 18953464, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 5-morpholino-imidazo[1,5-a]quinazoline-3-carboxylate (2.5 g, 7.7 mmol), cyclopropanecarboxamide oxime (3.8 g), crushed 4 Å molecular sieves (7.5 g), and sodium hydride (0.3 g, 60% in mineral oil, 7.7 mmol) in 50 ml of dry DMF was stirred at room temperature for 1 hour. Glacial acetic acid (2 ml) and dichloromethane (75 ml) were added, and the mixture was filtered through celite. The filtrate was evaporated and the residue was triturated with water (100 ml). Pale yellow crystals precipitated and were collected by filtration and dried to give 2.3 g of the title compound, m.p. 189°-191° C. A pure product was obtained by recrystallization from CH2Cl2 /ethyl acetate; yield 1.9 g (69%), m.p. 197°-198° C.

Workup

  1. filtrationthe mixture was filtered through celite
  2. customThe filtrate was evaporated
  3. customthe residue was triturated with water (100 ml)
  4. customPale yellow crystals precipitated
  5. filtrationwere collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-bde4997e15b2436d8a971a604505ef2d
Source dataset
uspto-grants-1994_12
Patent number
US05371080

Reaction notes

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