Methanol → HCID 70016891, compound

HRID 1585879Notes

Reaction equation

HRID 1585879 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]2=[O:16])=[CH:5][CH:4]=1.C(N1C=[C:39]([CH2:41][C:42]2[CH:49]=[CH:48][C:45]([C:46]#[N:47])=[CH:44][CH:43]=2)[N:38]=[CH:37]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CO.C[C:53]#[N:54]>>[Cl:15][C:13]1[CH:12]=[CH:11][C:10](=[O:16])[N:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:38]3[CH:37]=[CH:53][N:54]=[C:39]3[CH2:41][C:42]3[CH:43]=[CH:44][C:45]([C:46]#[N:47])=[CH:48][CH:49]=3)=[CH:4][CH:5]=2)[CH:14]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6342AcetonitrileHCID 158375331-Trityl-4-(4-cyanobenzyl)imidazoleHCID 18779697HCID 18779697, compound

Product 1

HCID 70016891HCID 70016891, compound

Procedure

The bromide from Step 2 (0.154 g, 0.516 mmol) and 4-(1-trityl-1H-imidazol-4-ylmethyl)-benzonitrile (0.22 g, 0.516 mmol) in CH3CN (2 mL) were heated at 55° C. After 18 hr methanol (3 mL) was added and the reaction was heated at reflux for 3 hrs, cooled and the solvent evaporated in vacuo. The residue was partitioned between sat. NaHCO3 and CH2Cl2 and extracted with CH2Cl2. The organic extracts were dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed (silica gel, MeOH: CH2Cl2 5:95 as eluent) to afford the free base which was converted to the hydrochloride salt to afford the title compound as a white solid.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 3 hrs
  3. temperaturecooled
  4. customthe solvent evaporated in vacuo
  5. customThe residue was partitioned between sat. NaHCO3 and CH2Cl2
  6. extractionextracted with CH2Cl2
  7. dry with materialThe organic extracts were dried (Na2SO4)
  8. customevaporated in vacuo
  9. customThe residue was chromatographed (silica gel, MeOH: CH2Cl2 5:95 as eluent)
  10. customto afford the free base which

Sources & evidence

ORD record
ord-79f86f0ce7bb4c0cb769ca2f5de86a82
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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