N'-Hydroxycyclopropanecarboximidamide → Imidazo[1,5-a]quinoxaline

HRID 1736697Notes

Reaction equation

HRID 1736697 reaction equation
CC(C)([O-])C.[K+].C1(C(=NO)N)CC1.C[C:15]1(C)[NH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]2[CH:25]=[N:26][C:27](C(OCC)=O)=[C:16]12>C1COCC1>[CH:25]1[N:17]2[C:18]3[C:23]([N:24]=[CH:15][C:16]2=[CH:27][N:26]=1)=[CH:22][CH:21]=[CH:20][CH:19]=3

Participants

5

Reactant 3

HCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 23665647Potassium tert-butoxideHCID 54175730Ethyl 4,5-Dihydro-4,4-dimethylimidazo[1,5-a]quinoxaline-3-carboxylate

Product 1

HCID 12658625Imidazo[1,5-a]quinoxaline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium tert-butoxide (1M in THF, 1.95 ml) is added to cyclopropylcarboxamide oxime (0.195 g) in THF (7 ml) at 0°. After 10 min ethyl 4,5-dihydro-4,4-dimethylimidazo[1,5-a]quinoxaline-3-carboxylate (XXXIII, EXAMPLE 94, 0.503 g) is added. The ice bath is removed after stirring for 10 min and the reaction is allowed to slowly warm to 20°-25°. After 2 hr DMF (4 ml) is added. When the reaction had stirred for a total of 7 hr, the solvents are removed under reduced pressure and the residue is partitioned between ethyl acetate and saline. The phases are separated, the organic phase is dried over magnesium sulfate and concentrated to give the title compound; mp 175°-179°; NMR (CDCl3): 1.10, 1.76, 2.18, 3.83, 6.79, 6.85, 7.13, 7.42 and 8.10 δ.

Workup

  1. customThe ice bath is removed
  2. temperatureto slowly warm to 20°-25°
  3. additionAfter 2 hr DMF (4 ml) is added
  4. stirringWhen the reaction had stirred for a total of 7 hr
  5. customthe solvents are removed under reduced pressure
  6. customthe residue is partitioned between ethyl acetate and saline
  7. customThe phases are separated
  8. dry with materialthe organic phase is dried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d3784a4b26f04fabad9ab64d8e9463d0
Source dataset
uspto-grants-1996_07
Patent number
US05541324

Reaction notes

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