Acetic Acid → HCID 67572402, compound

HRID 1741500Notes

Reaction equation

HRID 1741500 reaction equation
Cl.[C:2]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[C:13]([CH:14]=O)=[CH:12][N:11]=[CH:10]2)=[CH:6][CH:5]=1)#[N:3].[C:18](O)(=O)[CH3:19].[C:22]([BH3-])#[N:23].[Na+].CCO[C:29]([CH3:31])=O>CO.C1COCC1>[C:2]([C:4]1[CH:17]=[CH:16][C:7]([CH2:8][N:9]2[C:13]([CH2:14][NH:9][C@@H:13]([CH2:29][CH2:31][CH2:18][CH3:19])[CH2:12][NH:23][C:22]3[CH:7]=[CH:6][CH:5]=[C:4]([CH3:2])[C:17]=3[CH3:16])=[CH:12][N:11]=[CH:10]2)=[CH:6][CH:5]=1)#[N:3]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8857Ethyl Acetate2×HCID 5003444Sodium cyanoborohydrideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrile

Product 1

HCID 67572402HCID 67572402, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Through a solution of the product from Step 1 (533 mg, 1.47 mmol) in 20 mL of EtOAc at 0° C. was bubbled HCl gas. The saturated solution was warmed to room temperature and stirred for 40 minutes, then concentrated in vacuo. To a solution of this amine salt in 6 mL of 1:1 MeOH/THF at 0° C. was added the aldehyde from Step E (325 mg, 1.54 mmol) and 0.05 mL of acetic acid. After one hour, sodium cyanoborohydride was added (97 mg, 1.54 mmol), and the solution was allowed to warm to room temperature overnight. After ~16 hours, the reaction was poured into EtOAc, washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was purified by silica gel chromatography (1-2% MeOH/CHCl3). A portion of this was taken up in EtOAc/Et2O and treated with excess HCl gas, then stripped to provide the titled compound.

Workup

  1. concentrationconcentrated in vacuo
  2. waitAfter one hour
  3. temperatureto warm to room temperature overnight
  4. waitAfter ~16 hours
  5. washwashed with sat. aq. NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting product was purified by silica gel chromatography (1-2% MeOH/CHCl3)
  10. additiontreated with excess HCl gas

Sources & evidence

ORD record
ord-e021023b72774d2586ebf4dc2a9206b6
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

Loading…