Sulfuric Acid → HCID 22063817, compound

HRID 1828166Notes

Reaction equation

HRID 1828166 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:29]C(=O)C)[NH:11][C:12]=2[C:13]2[CH:28]=[CH:27][C:16]3[N:17]([CH:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[C:18](=[O:21])[N:19]([CH3:20])[C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O>CO.O>[ClH:1].[NH2:29][C:10]1[NH:11][C:12]([C:13]2[CH:28]=[CH:27][C:16]3[N:17]([CH:22]4[CH2:26][CH2:25][CH2:24][CH2:23]4)[C:18](=[O:21])[N:19]([CH3:20])[C:15]=3[CH:14]=2)=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:9]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 22063951HCID 22063951, compound

Product 1

HCID 22063817HCID 22063817, compoundYield 139%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirred solution of N-[4-(3-chloro-phenyl)-5-(1-cyclopentyl-3-methyl-2-oxo-2,3-dihydro-1H-benzoimidazol-5-yl)-1H-imidazol-2-yl]-acetamide (prepared as described above, 102 mg) in methanol:water (1:1, 10 mL) was added concentrated sulfuric acid (ca. 0.5 mL). The mixture was heated to reflux for 4 hours, after which the reaction was cooled to room temperature and the concentrated in vacuo. The resulting aqueous solution was diluted with water and the pH was adjusted to 10 with aqueous ammonium hydroxide. The mixture was filtered and the resulting white powder was taken up in 1M HCl in ether and concentrated in vacuo to afford 70 mg of the title compound as the HCl salt. MS (M+1)=408.1 (free base).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationthe concentrated in vacuo
  4. additionThe resulting aqueous solution was diluted with water
  5. filtrationThe mixture was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f76b1117b2604937961cc1002b9567f4
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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