Water → 3-[5-Amino-4-(3-pyrazin-2-yl-benzoyl)-imidazol-1-yl]-N-cyclopropyl-4-methylbenzamide

HRID 251376Notes

Reaction equation

HRID 251376 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])[CH:5]=[N:4][C:3]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23](Br)[CH:22]=1.O.O1[CH2:35][CH2:34]OCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[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])[CH:5]=[N:4][C:3]=1[C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:35]2[CH:34]=[N:4][CH:3]=[CH:2][N:1]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 312751,4-DioxaneHCID 58089004HCID 58089004, compound

Product 1

HCID 580889393-[5-Amino-4-(3-pyrazin-2-yl-benzoyl)-imidazol-1-yl]-N-cyclopropyl-4-methylbenzamideYield 63%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

A solution of 3-[5-amino-4-(3-bromobenzoyl)-imidazol-1-yl]-N-cyclopropyl-4-methylbenzamide (60 mg), 2-tributyltinpyrazine (120 uL) and tetrakis(triphenylphosphine)palladium(0) (30 mg) in 1,4-dioxane (0.8 mL) was heated under microwave radiation at 160° C. for 25 min. Water (3 ml) was added and the mixture was extracted with ethyl acetate (4 mL×2). Evaporation of the solvent and purification by preparatory TLC (EtOAc:MeOH=10:1) gave the desired product (38 mg, 63%). HPLC (4 minute 10-90 gradient) tR 2.18 min; MS m/z 439.27 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (4 mL×2)
  2. customEvaporation of the solvent and purification by preparatory TLC (EtOAc:MeOH=10:1)

Sources & evidence

ORD record
ord-4b58b0d18b094f21adb4dcbe939de2bd
Source dataset
uspto-grants-2011_01
Patent number
US07863314B2

Reaction notes

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