Hydrochloric Acid → HCID 178490878, compound

HRID 1370134Notes

Reaction equation

HRID 1370134 reaction equation
[O-:1][C:2]#[N:3].[K+].[NH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]#[N:22])=[CH:20][C:15]=3[N:14]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([Cl:32])[CH:25]=3)[C:13]2=[O:33])[CH2:8][CH2:7]1.Cl>O.O1CCOCC1>[NH:5]([C@H:6]1[CH2:11][CH2:10][C@H:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([C:21]#[N:22])=[CH:20][C:15]=3[N:14]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([Cl:32])[CH:25]=3)[C:13]2=[O:33])[CH2:8][CH2:7]1)[C:2]([NH2:3])=[O:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 11378442Potassium cyanateHCID 178490877HCID 178490877, compound

Product 1

HCID 178490878HCID 178490878, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of potassium cyanate (40 mg) in water (1 mL) was added to a mixture of 1-(trans-4-aminocyclohexyl)-3-(3-chloro-4-methoxybenzyl)-5-cyano-2,3-dihydro-1H-benzimidazol-2-one (100 mg) and 1N-hydrochloric acid (0.25 mL) in 1,4-dioxane (1.4 mL). The reaction mixture was stirred at ambient temperature for 20 hours. The mixture was partitioned between ethyl acetate and water. The separated organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was triturated with diethyl ether and washed with isopropyl alcohol to give 1-(trans-4-ureidocyclohexyl)-3-(3-chloro-4-methoxybenzyl)-5-cyano-2,3-dihydro-1H-benzimidazol-2-one (71mg) as powders.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was triturated with diethyl ether
  6. washwashed with isopropyl alcohol

Sources & evidence

ORD record
ord-2ec2e2de838a47d4886276e5ef545325
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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