Hydrochloric Acid → HCID 67572402, compound

HRID 1292695Notes

Reaction equation

HRID 1292695 reaction equation
C(O[C:6]([NH:8][C@@H:9]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:10][N:11]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[CH3:22])C(=O)C)=O)(C)(C)C.Cl.[C:28]([C:30]1[CH:43]=[CH:42][C:33]([CH2:34][N:35]2[C:39](C=O)=[CH:38][N:37]=[CH:36]2)=[CH:32][CH:31]=1)#[N:29].C([BH3-])#N.[Na+]>CCOC(C)=O.CO.C1COCC1.C(O)(=O)C>[C:28]([C:30]1[CH:31]=[CH:32][C:33]([CH2:34][N:35]2[C:39]([CH2:6][NH:8][C@@H:9]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:10][NH:11][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=3[CH3:22])=[CH:38][N:37]=[CH:36]2)=[CH:42][CH:43]=1)#[N:29]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5003444Sodium cyanoborohydrideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrileHCID 18660148HCID 18660148, compound

Product 1

HCID 67572402HCID 67572402, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Through a solution of the product from Step I (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 (Na2 SO4), 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. customdried (Na2 SO4)
  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-12a37a28a77c469789949c7f2aa23c62
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

Loading…