Chloroethane → HCID 18918190, compound

HRID 1290774Notes

Reaction equation

HRID 1290774 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]([NH:19][CH:20]=O)[C:7]3[N:12]4[CH:13]=[CH:14][N:15]=[C:11]4[C:10](=[O:16])[NH:9][C:8]=3[C:17]=2[CH:18]=1.B.CSC.CCCl>O1CCOCC1.O1CCCC1.C(O)C.CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]([NH:19][CH3:20])[C:7]3[N:12]4[CH:13]=[CH:14][N:15]=[C:11]4[C:10](=[O:16])[NH:9][C:8]=3[C:17]=2[CH:18]=1

Participants

8

Reactant 3

HCID 6337ChloroethaneHCID 12423031(Dimethyl sulfide)trihydroboronHCID 18918182HCID 18918182, compound

Product 1

HCID 18918190HCID 18918190, compoundYield 55.8%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To 0.8 g of 7-chloro-10-formamido-5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one suspended in 25 ml of anhydrous dioxane at 10° C. are added 6.7 ml of 2M borane/dimethyl sulphide solution in tetrahydrofuran over approximately 1 hour. The reaction mixture is stirred for 15 hours at a temperature in the region of 20° C. and is then treated with 20 ml of methanol and left for an additional 1 hour at the same temperature. After concentration to dryness under reduced pressure (15 mmHg; 2 kPa), the residue obtained is purified by flash chromatography on a column of silica, using a mixture of dichloromethane and methanol (95/5 by volume) as eluent. The product obtained (0.43 g) dissolved in a mixture of ethanol and methanol (1/1 by volume) is acidified using hydrochloric ether to give 0.24 g of 7-chloro-10-methylamino-5H,10H-imidazo-[1,2-a]indeno[1,2-e]pyrazin-4-one hydrochloride, in the form of a greenish-white powder the melting point of which is greater than 260° C. (Analysis C20H14ClN5O2 ·0.24 EtOH·0.15 H2O % calculated C: 44.53; H: 4.00; Cl: 28.16; N: 14.84; % found C: 44.5; H: 3.9; Cl: 28.1; N: 14.7).

Workup

  1. waitleft for an additional 1 hour at the same temperature
  2. concentrationAfter concentration to dryness under reduced pressure (15 mmHg; 2 kPa)
  3. customthe residue obtained
  4. customis purified by flash chromatography on a column of silica
  5. additiona mixture of dichloromethane and methanol (95/5 by volume) as eluent
  6. customThe product obtained (0.43 g)

Sources & evidence

ORD record
ord-a9a455d9488a4e84aa150961343ce5d7
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

Loading…