Dimethylformamide → 3-[5-Amino-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-1H-imidazole-4-carbonyl]-benzoic acid

HRID 884781Notes

Reaction equation

HRID 884781 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.ON1C(=O)CC[C:41]1=[O:46].C[CH:48]([NH2:50])C.CN(C=[O:55])C>CCOC(C)=O.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9]([C:10](=[O:11])[NH:12][CH:33]3[CH2:34][CH2:35]3)[CH:15]=[CH:16][C:17]=2[CH3:18])[CH:48]=[N:50][C:3]=1[C:19]([C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[C:41]([OH:46])=[O:55])=[O:27]

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 580890333-[5-Amino-1-(5-cyclopropylcarbamoyl-2-methyl-phenyl)-1H-imidazole-4-carbonyl]-benzoic acidYield 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×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×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-dcdd966ae917443eb0c78465863a79de
Source dataset
uspto-grants-2012_08
Patent number
US08242117B2

Reaction notes

Loading…