Hydrochloric Acid → HCID 22349401, compound

HRID 896387Notes

Reaction equation

HRID 896387 reaction equation
Cl[CH2:2][C:3]1[C:11]2[N:10]=[C:9]([CH2:12][N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[N:15]([CH:22]([CH3:24])[CH3:23])[C:14]3=[O:25])[N:8]([CH2:26][CH2:27][CH:28]([CH3:30])[CH3:29])[C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl.[C-:32]#[N:33].[Na+]>CS(C)=O>[CH:22]([N:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N:13]([CH2:12][C:9]2[N:8]([CH2:26][CH2:27][CH:28]([CH3:29])[CH3:30])[C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][C:32]#[N:33])[C:11]=3[N:10]=2)[C:14]1=[O:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 20813979HCID 20813979, compound

Product 1

HCID 22349401HCID 22349401, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution containing 1-[4-chloromethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one; HCl salt (69 mg, 0.15 mmol) and sodium cyanide (30 mg, 0.62 mmol) in DMSO (1.5 mL) was stirred at room temperature for 1.5 h. The mixture was quenched with water (15 mL) and 1M NaOH (0.5 mL). The aqueous suspension was extracted with diethyl ether (2×10 mL) and the combined organic extracts washed with water, brine and dried (MgSO4). [2-(3-Isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-4-yl]-acetonitrile was obtained after concentration as a white solid (55 mg, 89%) and was used in the next step without purification:

Workup

  1. customThe mixture was quenched with water (15 mL) and 1M NaOH (0.5 mL)
  2. extractionThe aqueous suspension was extracted with diethyl ether (2×10 mL)
  3. washthe combined organic extracts washed with water, brine
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-e5170a581fb6473795ba2362aa1ec932
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

Loading…