creatinine → 4-fluoro-N-(3-methyl-5-oxo-4H-imidazol-2-yl)-3-(6-propan-2-ylquinolin-8-yl)benzamide

HRID 857301

Reaction equation

HRID 857301 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]([CH:21]([CH3:23])[CH3:22])[CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2.CCN=C=NCCCN(C)C.[NH2:35][C:36]1[N:37]([CH3:42])[CH2:38][C:39](=[O:41])[N:40]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:35][C:36]2[N:37]([CH3:42])[CH2:38][C:39](=[O:41])[N:40]=2)=[O:7])=[CH:4][C:3]=1[C:11]1[CH:12]=[C:13]([CH:21]([CH3:22])[CH3:23])[CH:14]=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2

Participants

7

Reactant 3

HCID 588creatinineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218655434-Fluoro-3-(6-isopropyl-quinolin-8-yl)-benzoic acid

Product 1

HCID 1784387944-fluoro-N-(3-methyl-5-oxo-4H-imidazol-2-yl)-3-(6-propan-2-ylquinolin-8-yl)benzamide

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To solution of the 4-fluoro-3-(6-isopropyl-quinolin-8-yl)-benzoic acid from Step 2 (1.0 eq), EDCI (1.1 eq) and DMAP (1.1 eq) in CH2Cl2 (0.07M) was added 2-amino-1-methyl-1,5-dihydro-imidazol-4-one (1.1 eq). The resulting mixture was stirred for 12 h, poured in saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (EtOAc) afforded the compound as a white solid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a44bb52dd197423984a41fcf35bb74e5
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Linked notes

Loading…