Hydrogen Sulfide → HCID 60064160, compound

HRID 412545Notes

Reaction equation

HRID 412545 reaction equation
S.[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:35][C:36]3[N:40]([CH2:41][C:42](=[O:52])[NH:43][C@H:44]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[CH3:45])[C:39]4[CH:53]=[CH:54][C:55]([C:57]#[N:58])=[CH:56][C:38]=4[N:37]=3)[C:23](=[O:34])[C:24]3[CH:29]=[CH:28][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:26][CH:25]=3)=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3].[N:59]1C=CC(CCN)=C(CCN)C=1CCN>>[C:2]([O:6][C:7]([N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:17]=[CH:18][C:19]([N:22]([CH2:35][C:36]3[N:40]([CH2:41][C:42](=[O:52])[NH:43][C@H:44]([C:46]4[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=4)[CH3:45])[C:39]4[CH:53]=[CH:54][C:55]([C:57]([NH2:59])=[NH:58])=[CH:56][C:38]=4[N:37]=3)[C:23](=[O:34])[C:24]3[CH:25]=[CH:26][C:27]([C:30]([O:32][CH3:33])=[O:31])=[CH:28][CH:29]=3)=[CH:20][CH:21]=2)[CH2:11][CH2:10]1)=[O:8])([CH3:3])([CH3:4])[CH3:5]

Participants

4

Reactant 3

HCID 402Hydrogen SulfideHCID 67712788HCID 67712788, compoundHCID 69698053HCID 69698053, compound

Product 1

HCID 60064160HCID 60064160, compound

Procedure

Hydrogen sulfide was blown into a solution of (S)-2-[N-[4-(1-tert-butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonylbenzoyl)-aminomethyl]-5-cyano-1-(1-phenylethylcarbamoylmethyl)benzimidazole (284 mg) in a mixture of pyridin-triethylamine (5:1) (10 ml) with ice-cooling, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the solvent was evaporated and the residue was treated with hydrogen chloride-ethanol. Thereto were added acetone (6 ml), methanol (6 ml) and methyl iodide (0.229 ml), and the mixture was stirred under reflux for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was dissolved in ethanol (12 ml). Ammonium acetate (43 mg) was added, and the mixture was stirred at 75° C. for 2 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:5-90:10) and dried under reduced pressure to give the title compound (113 mg).

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. additionthe residue was treated with hydrogen chloride-ethanol
  5. additionThereto were added acetone (6 ml), methanol (6 ml) and methyl iodide (0.229 ml)
  6. stirringthe mixture was stirred
  7. temperatureunder reflux for 2 hours
  8. customAfter completion of the reaction
  9. customthe solvent was evaporated
  10. dissolutionthe obtained residue was dissolved in ethanol (12 ml)
  11. additionAmmonium acetate (43 mg) was added
  12. stirringthe mixture was stirred at 75° C. for 2 hours
  13. customAfter completion of the reaction
  14. customthe solvent was evaporated
  15. customthe obtained residue was purified by silica gel column chromatography (chloroform:methanol=95:5-90:10)
  16. customdried under reduced pressure

Sources & evidence

ORD record
ord-4faa84dd24a447bc9ab3fb3ddef1bd64
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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