Triethylamine → HCID 18975441, compound

HRID 2393423Notes

Reaction equation

HRID 2393423 reaction equation
Cl.[NH2:2][C:3]1([CH3:25])[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([NH:20][C:21]([NH:23][CH3:24])=[O:22])=[CH:5][C:4]1=2.C(N(CC)CC)C>CO>[NH2:2][C:3]1([CH3:25])[C:15]2[N:14]3[CH:16]=[CH:17][N:18]=[C:13]3[C:12](=[O:19])[NH:11][C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([NH:20][C:21]([NH:23][CH3:24])=[O:22])=[CH:5][C:4]1=2

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 18975494HCID 18975494, compound

Product 1

HCID 18975441HCID 18975441, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.4 g of 10-amino-10-methyl-8-(3-methyl-ureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride dissolved in 25 ml of methanol containing triethylamine is chromatographed on a 23 cm column 6 cm in diameter packed with 400 g of silica coated with cellulose tris(3,5-dimethylphenylcarbamate) (Chiralcel OD type). The elution is carried out using a heptane/ethanol mixture (20/80 by volume) containing 0.05% triethylamine. The flow rate is 35 ml per minute and UV detection is performed at 254 nm. This operation is repeated 15 times in order to produce the two enantiomers of 10-amino-10-methyl-8-(3-methylureido)-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one after concentration to dryness under reduced pressure of the fractions obtained: 1.79 g of laevorotatory enantiomer ([α]20D =-90.3°±1.2°) are thus isolated first, in the form of a white powder decomposing without melting at about 200° C. (Analysis, C16H16N6O2.0.21 H2 O.1.0 EtOH % calculated C: 59.25; H: 4.97; N: 25.91, % found C: 59.5; H: 4.9; N: 25.7); 1.47 g of the dextrorotatory enantiomer ([α]20D =89.00°±10°) are then isolated in the form of a pale yellow powder decomposing without melting at about 200° C. (Analysis, C16H16N6O2.0.21 H2 O.1.0 EtOH % calculated C: 59.25; H: 4.97; N: 25.91; % found C: 59.6; H: 5.0; N: 26.1). The purity of the two enantiomers is checked by chromatography under the same conditions (column: 25 cm/4.6 mm; Chiralcel OD type phase; eluent: EtOH/heptane: 80/20; flow rate: 1 ml/min; UV detection at 254 nm): the purity is greater than 98% for the first enantiomer and greater than 90% for the second.

Workup

  1. customis chromatographed on a 23 cm column 6 cm in diameter
  2. washThe elution
  3. additioncontaining 0.05% triethylamine

Sources & evidence

ORD record
ord-0017bc5e592a453aa316a49c6208e673
Source dataset
uspto-grants-1998_09
Patent number
US05807859

Reaction notes

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