Hydrochloric Acid → HCID 24800582, compound

HRID 1991479Notes

Reaction equation

HRID 1991479 reaction equation
Cl.C(OC(=O)[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]([C:30](=O)[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)[CH:16]([C:21](=[O:29])[NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:17][CH:18]([CH3:20])[CH3:19])(C)(C)C>CO>[CH:23]1([NH:22][C:21](=[O:29])[CH:16]([N:15]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=[C:30]2[C:31]2[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=2)[CH2:17][CH:18]([CH3:20])[CH3:19])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68696541HCID 68696541, compound

Product 1

HCID 24800582HCID 24800582, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
145 °C

Procedure

Concentrated HCl (25% in water, 0.5 mL) was added to a solution of crude {2-[(4-chloro-benzoyl)-(1-cyclohexylcarbamoyl-3-methyl-butyl)-amino]-phenyl}-carbamic acid tert-butyl ester (83 mg, 0.12 mmol) in methanol (2.0 mL). The reaction mixture was heated in a focussed microwave (CEM Discovery) at 145° C., for 3 minutes with stirring. The reaction mixture was then evaporated, purified by preparative HPLC (gradient elution: water/acetonitrile with 0.1% trifluoroacetic acid) and evaporated under vacuum. This was then re-dissolved in dichloromethane (2 mL), PS-carbonate resin (4 mmol/g, 100 mg) was added and the mixture shaken for 2 hours. The mixture was filtered and evaporated to afford 2-[2-(4-chloro-phenyl)-benzoimidazol-1-yl]-4-methyl-pentanoic acid cyclohexylamide, 30 mg (46%) as a white solid. MS (ES+): 424 (M+H).

Workup

  1. customThe reaction mixture was then evaporated
  2. custompurified by preparative HPLC (gradient elution: water/acetonitrile with 0.1% trifluoroacetic acid)
  3. customevaporated under vacuum
  4. dissolutionThis was then re-dissolved in dichloromethane (2 mL)
  5. additionPS-carbonate resin (4 mmol/g, 100 mg) was added
  6. stirringthe mixture shaken for 2 hours
  7. filtrationThe mixture was filtered
  8. customevaporated

Sources & evidence

ORD record
ord-4908ffe2dfef4a5191f04c4b5f5e36aa
Source dataset
uspto-grants-2010_01
Patent number
US07645785B2

Reaction notes

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