Dichloromethane → HCID 21994557, compound

HRID 1197442Notes

Reaction equation

HRID 1197442 reaction equation
[CH2:1]([N:3]([C:5]1[C:6]2[N:7]([CH:15]=[N:16][C:17]=2[C:18]([O:20]CC)=O)[C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:4])[CH3:2].[CH:23]1([C:26](=[N:28]O)[NH2:27])[CH2:25][CH2:24]1.[H-].[Na+].ClCCl>CN(C=O)C>[CH:23]1([C:26]2[N:28]=[C:18]([C:17]3[N:16]=[CH:15][N:7]4[C:8]5[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=5)[N:14]=[C:5]([N:3]([CH2:1][CH3:2])[CH3:4])[C:6]=34)[O:20][N:27]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 2794666N'-HydroxycyclopropanecarboximidamideHCID 19106541HCID 19106541, compound

Product 1

HCID 21994557HCID 21994557, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 4-(N-ethyl-N-methylamino)-imidazo[1,5-a]quinoxaline-3-carboxylate (1.2 g, 4 mmol), cyclopropanecarboxamidoxime (1.4 g, 14 mmol), crushed 4 Å molecular-sieves (0.5 g), and sodium hydride (0.1 g, 60% in mineral oil) in dry DMF (20 ml) was stirred at ambient temperature for 1 h. Dichloromethane (25 ml) was added and the mixture was filtered through celite. The filtrate was evaporated and the residue was brought to crystallize by the addition of 10 ml of ethyl acetate and cooling to 0° C. The crystals was collected by filtration, rinsed with ethyl acetate and dried to give 0.58 g of the title compound, m.p. 96°-97° C. An additional amount (0.22 g) of the product was obtained from the mother liquour. (Compound 6).

Workup

  1. filtrationthe mixture was filtered through celite
  2. customThe filtrate was evaporated
  3. customto crystallize by the addition of 10 ml of ethyl acetate
  4. temperaturecooling to 0° C
  5. filtrationThe crystals was collected by filtration
  6. washrinsed with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-d5367b527ae84fa698623b7207b7c4a4
Source dataset
uspto-grants-1994_01
Patent number
US05276028

Reaction notes

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