Acetic Acid → HCID 18953411, compound

HRID 1491615Notes

Reaction equation

HRID 1491615 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[N:13][C:14]([C:15]([O:17]CC)=O)=[C:7]1[N:6]=[C:5]2[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C[CH:27](C)[CH2:28][C:29](=[N:31]O)[NH2:30].[H-].[Na+].[C:36](O)(=O)C>CN(C=O)C.ClCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[N:13][C:14]([C:15]3[O:17][N:31]=[C:29]([CH:28]([CH3:36])[CH3:27])[N:30]=3)=[C:7]1[N:6]=[C:5]2[N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydride2×HCID 4985512HCID 4985512, compoundHCID 18953415HCID 18953415, compound

Product 1

HCID 18953411HCID 18953411, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 7-fluoro-5-morpholino-imidazo[1,5-a]quinazoline-3-carboxylate (1.6 g), 2-methyl-1-propanecarboxamide oxime (2.4 g), crushed 4 Å molecular sieves (3.5 g), and sodium hydride (0.14 g, 80% in mineral oil) in 20 ml of dry DMF was stirred at ambient temperature. After 1 hour an additional amount of the carboxamide oxime (2.4 g) and sodium hydride suspension (0.14 g) was added, and the mixture was stirred for one more hour. Glacial acetic acid (2 ml) and dichloromethane (50 ml) were added, and after the precipitated product had dissolved the sieves were removed by filtration through celite. The filtrate was evaporated and the residue was triturated with 100 ml of water. The undissolved material was collected by filtration, dried and treated with 25 ml of acetone. Yellow crystals precipitated and were filtered off and dried. Yield 0.47 g, m.p. 262°-264° C.

Workup

  1. stirringthe mixture was stirred for one more hour
  2. dissolutionafter the precipitated product had dissolved the sieves
  3. customwere removed by filtration through celite
  4. customThe filtrate was evaporated
  5. customthe residue was triturated with 100 ml of water
  6. filtrationThe undissolved material was collected by filtration
  7. customdried
  8. additiontreated with 25 ml of acetone
  9. customYellow crystals precipitated
  10. filtrationwere filtered off
  11. customdried

Sources & evidence

ORD record
ord-b6b6faecf7e84d929bb96fd570efcfc2
Source dataset
uspto-grants-1994_12
Patent number
US05371080

Reaction notes

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