Butanoic acid, 4-chloro-4-oxo-, methyl ester → 4-[3-(3-Fluoro-phenylamino)-6,7-dimethoxy-4H-indeno[1,2-c]pyrazol-1-yl]-4-oxo-butyric acid methyl ester

HRID 460351

Reaction equation

HRID 460351 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:20](=[CH:21][C:22]=1[O:23][CH3:24])[C:8]1[NH:9][N:10]=[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)[C:7]=1[CH2:6]2.[CH3:25][O:26][C:27](=[O:33])[CH2:28][CH2:29][C:30](Cl)=[O:31].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:25][O:26][C:27](=[O:33])[CH2:28][CH2:29][C:30]([N:9]1[C:8]2[C:20]3[C:5]([CH2:6][C:7]=2[C:11]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=2)=[N:10]1)=[CH:4][C:3]([O:2][CH3:1])=[C:22]([O:23][CH3:24])[CH:21]=3)=[O:31]

Participants

5

Reactant 3

HCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl ester2×HCID 81531DiisopropylethylamineHCID 9797370Jnj-101984092×

Product 1

HCID 588248264-[3-(3-Fluoro-phenylamino)-6,7-dimethoxy-4H-indeno[1,2-c]pyrazol-1-yl]-4-oxo-butyric acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (6,7-Dimethoxy-1,4-dihydro-indeno[1,2-c]pyrazol-3-yl)-(3-fluoro-phenyl)-amine (Compound 14) (0.50 g, 1.5 mmol), 3-Chlorocarbonyl-propionic acid methyl ester (Compound 26a) (0.277 g, 1.8 mmole) and DMF (1.5 mL) was added Diisopropylethylamine (DIEA) (0.52 mL, 3.0 mmole) at room temperature with stirring. The reaction was stirred at room temperature over night. The reaction was quenched with water and extracted with EtOAc. The solvent was removed via rotovap and the crude material was prepped on the reverse phase HPLC. Lyophilization gave the title compound as a white powder. MS m/z439.9 (M+H)+;

Workup

  1. stirringThe reaction was stirred at room temperature over night
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. customThe solvent was removed via rotovap

Sources & evidence

ORD record
ord-3032bbf713c84279888a4b6191ba6e7f
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Linked notes

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