Phenylacetyl chloride → HCID 18790722, compound

HRID 1107039Notes

Reaction equation

HRID 1107039 reaction equation
[CH2:1]([N:3](CC)CC)C.[C:8]1([CH2:14][C:15](Cl)=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.NC[C:21]1[CH:37]=[CH:36][C:35]2[C:26]3[NH:27][C:28](=[O:34])[C:29]4[N:30]([CH:31]=[CH:32][N:33]=4)[C:25]=3[CH2:24][C:23]=2[CH:22]=1>CN(C)C=O>[O:34]=[C:28]1[NH:27][C:26]2[C:35]3[CH:36]=[CH:37][CH:21]=[C:22]([CH2:1][NH:3][C:15](=[O:16])[CH2:14][C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:23]=3[CH2:24][C:25]=2[N:30]2[CH:31]=[CH:32][N:33]=[C:29]12

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 18790726HCID 18790726, compound

Product 1

HCID 18790722HCID 18790722, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.4 ml of triethylamine and 0.9 ml of phenylacetyl chloride are added to a suspension of 1 g of 8-aminomethyl-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride in 40 ml of dimethylformamide. After reacting for 16 hours at a temperature in the region of 20° C., the reaction mixture is filtered and the filtrate is evaporated under reduced pressure. The residue is suspended in 50 ml of acetone. After filtration and drying under reduced pressure (1 mbar) at 60° C., 100 mg of N-[(4,5-dihydro-4-oxo-10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-9-yl)methyl]phenylacetamide are obtained in the form of a beige solid melting above 260° C. (1H NMR spectrum in d6-DMSO, T=300 K, δ in ppm: 3.51 (2H, s, CH2 -Ph), 3.97 (2H, s, CH2), 4.35 (2H, d, J=4 Hz, NCH2), between 7.20 and 7.40 (6H, m, arom. H), 7.43 (1H, s, arom. CH), 7.60 (1H, s, arom. CH), 7.78 (1H, d, J=7 Hz, arom. CH), 7.98 (1H, s, arom. CH), 8.63 (1H, broad t, NH), 12.3 (1H, s, NH)).

Workup

  1. filtrationthe reaction mixture is filtered
  2. customthe filtrate is evaporated under reduced pressure
  3. filtrationAfter filtration
  4. customdrying under reduced pressure (1 mbar) at 60° C.

Sources & evidence

ORD record
ord-3a37d83ed5e34563a39f7b67ed0bb152
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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