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

HRID 460358Notes

Reaction equation

HRID 460358 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.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28].C(N(C(C)C)CC)(C)C>C1COCC1>[C:30]1([O:29][C:27]([N:10]2[C:9]3[C:21]4[C:6]([CH2:7][C:8]=3[C:12]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)=[N:11]2)=[CH:5][C:4]([O:3][CH3:2])=[C:23]([O:24][CH3:25])[CH:22]=4)=[O:28])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformate2×HCID 81531DiisopropylethylamineHCID 178486504HCID 178486504, compound2×

Product 1

HCID 588248603-(3-Fluoro-phenylamino)-6,7-dimethoxy-4H-indeno[1,2-c]pyrazole-1-carboxylic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (6,7-Dimethoxy-1,4-dihydro-indeno[1,2-c]pyrazol-3-yl)-(3-fluoro-phenyl)-amine (Compound 14) (1.5 g g, 4.2 mmol), Phenyl chloroformate (Compound 55a) (0.76 mL, 6.3 mmole) and THF (10 mL) was added Diisopropylethylamine (DIPEA) (1.4 mL, 8.4 mmole) at room temperature with stirring. The reaction was stirred at room temperature over night. The reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The solvent was dried over sodium sulfate and removed via rotovap to give a crude material (Compound 433). MS m/z 446.1 (M+H)+.

Workup

  1. stirringThe reaction was stirred at room temperature over night
  2. customThe reaction was quenched with saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe solvent was dried over sodium sulfate
  5. customremoved via rotovap

Sources & evidence

ORD record
ord-57b0e7427aa940f08f7aef9d3e715530
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Reaction notes

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