Sulfamide → HCID 178490879, compound

HRID 1370135Notes

Reaction equation

HRID 1370135 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:11]=3[N:10]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([Cl:28])[CH:21]=3)[C:9]2=[O:29])[CH2:4][CH2:3]1.[S:30](N)([NH2:33])(=[O:32])=[O:31]>COCCOC>[NH2:33][S:30]([NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]#[N:18])=[CH:16][C:11]=3[N:10]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([Cl:28])[CH:21]=3)[C:9]2=[O:29])[CH2:4][CH2:3]1)(=[O:32])=[O:31]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 178490877HCID 178490877, compound

Product 1

HCID 178490879HCID 178490879, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 1-(trans-4-aminocyclohexyl)-3-(3-chloro-4-methoxybenzyl)-5-cyano-2,3-dihydro-1H-benzimidazol-2-one (90 mg) and sulfamide (42 mg) in ethylene glycol dimethyl ether (3 mL) was refluxed overnight. The mixture was concentrated in vacuo, and the residue was partitioned between chloroform and water. The separated organic layer was washed with an aqueous saturated sodium chloride solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was subjected to a preparative thin-layer chromatography eluting with a mixture of chloroform and methanol (10:1). The obtained crystals were collected by filtration and washed with diethyl ether to give 1-(trans-4-aminosulfonamidocyclohexyl)-3-(3-chloro-4-methoxybenzyl)-5-cyano-2,3-dihydro-1H-benzimidazol-2-one (41 mg) as powders.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was partitioned between chloroform and water
  4. washThe separated organic layer was washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. washeluting with a mixture of chloroform and methanol (10:1)
  8. filtrationThe obtained crystals were collected by filtration
  9. washwashed with diethyl ether

Sources & evidence

ORD record
ord-b5f9e07af8144d5f82ab845258a64132
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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