Diisopropylamine → 3-(3-Fluoro-phenylamino)-6,7-dimethoxy-4H-indeno[1,2-c]pyrazole-1-carboxylic acid isopropyl ester

HRID 460355Notes

Reaction equation

HRID 460355 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:21](=[CH:22][C:23]=1[O:24][CH3:25])[C:9]1=[N:10][NH:11][C:12]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)=[C:8]1[CH2:7]2.C(NC(C)C)(C)C.Cl[C:34]([O:36][CH:37]([CH3:39])[CH3:38])=[O:35]>C1COCC1>[CH:37]([O:36][C:34]([N:10]1[C:9]2[C:21]3[C:6]([CH2:7][C:8]=2[C:12]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)=[N:11]1)=[CH:5][C:4]([O:3][CH3:2])=[C:23]([O:24][CH3:25])[CH:22]=3)=[O:35])([CH3:39])[CH3:38]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 7917Isopropyl chloroformateHCID 178486504HCID 178486504, compound2×

Product 1

HCID 588249753-(3-Fluoro-phenylamino)-6,7-dimethoxy-4H-indeno[1,2-c]pyrazole-1-carboxylic acid isopropyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (6,7-Dimethoxy-2,4-dihydro-indeno[1,2-c]pyrazol-3-yl)-(3-fluoro-phenyl)-amine HCl (Compound 14) (0.50 g, 0.0014 mole), THF (10 mL), and Diisopropyl amine (0.512 mL, 0.00295 mole) was stirred until the solid completely dissolved. Isopropyl chloroformate (1.5 mL, 0.0015 mole) was added slowly at room temperature. The reaction mixture was stirred at room temperature overnight. The solvent was removed in vacuo from the resulting organics. Attempt to separate resulting isomers with reverse-phase chromatography was not successful. Placed isomer containing fractions in refrigerator. Much of major isomer crystallized. Filtered white crystals of title compound from solution (Compound 436). MS m/z 412 (M+H)+;

Workup

  1. dissolutioncompletely dissolved
  2. customThe solvent was removed in vacuo from the resulting organics
  3. customto separate
  4. customresulting isomers with reverse-phase chromatography
  5. additioncontaining fractions in refrigerator
  6. customMuch of major isomer crystallized
  7. filtrationFiltered white crystals of title compound from solution (Compound 436)

Sources & evidence

ORD record
ord-ed41e1fa020f4a88a62ca65497dca55a
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Reaction notes

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