Hydrochloric Acid → 3-(5-Amino-4-benzoyl-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide

HRID 2041038Notes

Reaction equation

HRID 2041038 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:15][CH2:14]2)=[O:11])N=CC=1C(=O)C1C=CC(C)=CC=1.[C:29]1([Mg]Br)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl.[OH-:38].[Na+]>C1COCC1>[NH2:6][C:7]1[N:6]([C:7]2[CH:8]=[C:9]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:10]([NH:12][CH:13]2[CH2:14][CH2:15]2)=[O:11])[CH:2]=[N:1][C:18]=1[C:17](=[O:38])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 111647033-[5-amino-4-(4-methyl-benzoyl)-pyrazol-1-yl]-N-cyclopropyl-4-methyl-benzamideHCID 178418255HCID 178418255, compound

Product 1

HCID 248606083-(5-Amino-4-benzoyl-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-amino-4-cyano-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide 3 (56.4 mg, 0.2 mmol) in dry THF (10 ml) under nitrogen was added phenylmagnesium bromide (1M, 1 mL) at room temperature. After 1 h, HCl solution (3N, 10 ml) was added and the mixture was stirred overnight. The solution was neutralized with dilute aqueous NaOH. The mixture was extracted with ethyl acetate (100 mL×2), washed with water and dried over Na2SO4. Evaporation of the solvent gave a residue which was purified by HPLC to give 3-(5-Amino-4-benzoyl-imidazol-1-yl)-N-cyclopropyl-4-methyl-benzamide as a while solid (56 mg, 78%). LCMS (4 minute gradient) tR=2.07 min; MS m/z 361.17 [M+H]

Workup

  1. extractionThe mixture was extracted with ethyl acetate (100 mL×2)
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent
  5. customgave a residue which
  6. customwas purified by HPLC

Sources & evidence

ORD record
ord-14d26af0d23341a6a80e0e6fa143bb62
Source dataset
uspto-grants-2013_11
Patent number
US08580838B2

Reaction notes

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