Tetrahydrofuran → HCID 59349495, compound

HRID 415119Notes

Reaction equation

HRID 415119 reaction equation
BrC1C=CC(C)=C([NH:8][C:9]([C:11]2[N:12]=[CH:13][N:14]3[C:19]=2C(=O)[N:17]2[CH:21]=[N:22][C:23]([C:24]([NH:26][C:27]4[CH:32]=[C:31]([Br:33])[CH:30]=[CH:29][C:28]=4[CH3:34])=[O:25])=[C:16]2[C:15]3=[O:35])=O)C=1.[CH2:37]1COCC1.CC1N=C(N)NC=1C>CN(C=O)C>[Br:33][C:31]1[CH:30]=[CH:29][C:28]([CH3:34])=[C:27]([NH:26][C:24]([C:23]2[N:22]=[CH:21][NH:17][C:16]=2[C:15]([NH:14][C:13]2[NH:8][C:9]([CH3:37])=[C:11]([CH3:19])[N:12]=2)=[O:35])=[O:25])[CH:32]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 124859204,5-Dimethyl-1H-imidazol-2-amineHCID 59349561HCID 59349561, compound

Product 1

HCID 59349495HCID 59349495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
53 °C

Procedure

A dry round bottomed flask was charged with N1,N6-bis(5-bromo-2-methylphenyl)-5,10-dioxo-5,10-dihydrodiimidazo[1,5-a:1′,5′-d]pyrazine-1,6-dicarboxamide (490 mg, 0.8 mmol) and anhydrous THF (15 ml). To this suspension was added 4,5-dimethyl-1H-imidazol-2-amine (196 mg, 1.76 mmol) in anhydrous DMF (2 ml). The reaction mixture was then stirred at 53° C. for 16 hours. The reaction mixture was then allowed to cool to room temperature and concentrated at reduced pressure. The crude material was treated with methanol and 1M hydrochloric acid. Saturated potassium carbonate solution was then added to neutralize the mixture. The resulting solid was filtered off, washed with 1M hydrochloric acid, saturated potassium carbonate solution and dichloromethane. Purification by reverse phase HPLC (aqueous ammonium acetate/acetonitrile) gave 32 mg of N4-(5-bromo-2-methylphenyl)-N5-(4,5-dimethyl-1H-imidazol-2-yl)-1H-imidazole-4,5-dicarboxamide. 1H-NMR (400 MHz, DMSO-d6): 7.97 (d, 1H), 7.35 (d, 1H), 7.27 (d, 1H), 2.29 (s, 3H), 2.04 (s, 6H); MS (EI): 418.5 (MO.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated at reduced pressure
  3. additionThe crude material was treated with methanol and 1M hydrochloric acid
  4. additionSaturated potassium carbonate solution was then added
  5. filtrationThe resulting solid was filtered off
  6. washwashed with 1M hydrochloric acid, saturated potassium carbonate solution and dichloromethane
  7. customPurification by reverse phase HPLC (aqueous ammonium acetate/acetonitrile)

Sources & evidence

ORD record
ord-469ee0571027461a9f7b967adcc42051
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

Loading…