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

HRID 884779Notes

Reaction equation

HRID 884779 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 x2), washed with water and dried over Na2SO4. Evaporation of the solvent gave a residue which was purifiedd 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 x2)
  2. washwashed with water
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent
  5. customgave a residue which

Sources & evidence

ORD record
ord-f5c06182b1de45b292e077b2f1ef68a4
Source dataset
uspto-grants-2012_08
Patent number
US08242117B2

Reaction notes

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