Benzimidazole → HCID 58284825, compound

HRID 2368833Notes

Reaction equation

HRID 2368833 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].NC1N=C(O)C=C(O)N=1.Br[C:26]1[S:30][C:29]([C:31](=[O:36])[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:28][CH:27]=1>O.CN1C(=O)CCC1>[N:1]1([C:26]2[S:30][C:29]([C:31](=[O:36])[CH2:32][CH2:33][CH2:34][CH3:35])=[CH:28][CH:27]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 5798BenzimidazoleHCID 10796Cesium carbonateHCID 58284813HCID 58284813, compoundHCID 178508985HCID 178508985, compound

Product 1

HCID 58284825HCID 58284825, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
157.5 °C

Procedure

Charged Benzimidazole (12.11 mmoles), cesium carbonate (14.11 mmoles), cuprous oxide (0.4 mmoles), 2-Amino-4,6-dihydroxypyrimidine (1.5 mmoles), PEG (catalyst), keto thiophene (XXI) and NMP (5 ml) to the RB flask fitted with thermo well and condenser. The reaction mixture was heated to 155-160° C. and the temperature was maintained for 10-12 hrs at 155-160° C. After completion of reaction, cooled to room temperature, added water (25 ml), extracted with ethyl acetate (2×100 ml), washed with 10% brine solution, dried the ethyl acetate layer over sodium sulfate and distilled off the solvent completely at reduced pressure to get crude compound. The crude compound was purified by using silica gel 60-120 silica gel column chromatography and DCM: methanol: 100-5% as mobile phase to get the pure compound (84).

Workup

  1. customfitted with thermo well and condenser
  2. temperaturethe temperature was maintained for 10-12 hrs at 155-160° C
  3. customAfter completion of reaction
  4. temperaturecooled to room temperature
  5. extractionextracted with ethyl acetate (2×100 ml)
  6. washwashed with 10% brine solution
  7. dry with materialdried the ethyl acetate layer over sodium sulfate
  8. distillationdistilled off the solvent completely at reduced pressure
  9. customto get crude compound
  10. customThe crude compound was purified

Sources & evidence

ORD record
ord-4b6522a3a4234694b27c712146c27314
Source dataset
uspto-grants-2014_04
Patent number
US08703811B2

Reaction notes

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