Dimethylformamide → 3-[5-Amino-4-(3-isopropylcarbamoyl-benzoyl)-imidazol-1-yl]-n-cyclopropyl-4-methyl-benzamide

HRID 251345Notes

Reaction equation

HRID 251345 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:10]([NH:12]OC)=[O:11])N=C[C:3]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22](I)[CH:21]=1.CCN=C=N[CH2:33][CH2:34][CH2:35]N(C)C.O[N:40]1[C:44](=[O:45])C[CH2:42][C:41]1=O.C[CH:48]([NH2:50])C.[CH3:51]N(C=O)C>CCOC(C)=O.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([CH:15]=[CH:16][C:17]=2[CH3:18])[C:10]([NH:12][CH:33]2[CH2:34][CH2:35]2)=[O:11])[CH:48]=[N:50][C:3]=1[C:19](=[O:27])[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:44](=[O:45])[NH:40][CH:41]([CH3:42])[CH3:51])[CH:21]=1

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 6363IsopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 117848203-[5-amino-4-(3-iodo-benzoyl)-pyrazol-1-yl]-N-methoxy-4-methyl-benzamide

Product 1

HCID 248606603-[5-Amino-4-(3-isopropylcarbamoyl-benzoyl)-imidazol-1-yl]-n-cyclopropyl-4-methyl-benzamideYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of acid 4 (160 mg), EDCI (90 mg), and N-hydroxysucinimide (53 mg) in DMF (2 mL) was reacted at rt overnight. Water (12 ml) was added and the solution was extracted with EtOAc (15 mL X 2), dried over Na2SO4. Evaporation of solvent gave a residue, into which EtOAc (4 mL) and 2-propylamine (1.2 eq) was added. The reaction was kept at rt for 1 h., then concentrated and the crude product purified by column chromatography to give the desired product (yield: 80%). HPLC (4 minute gradient) tR=2.00 min; MS m/z 446.19 [M+H]+.

Workup

  1. extractionthe solution was extracted with EtOAc (15 mL X 2)
  2. dry with materialdried over Na2SO4
  3. customEvaporation of solvent
  4. customgave a residue
  5. concentrationconcentrated
  6. customthe crude product purified by column chromatography

Sources & evidence

ORD record
ord-a17f2cf60f9044dfad82971a1bb2ffbb
Source dataset
uspto-grants-2011_01
Patent number
US07863314B2

Reaction notes

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