Potassium Carbonate → HCID 9929867, compound

HRID 489852Notes

Reaction equation

HRID 489852 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1.C([O-])([O-])=O.[K+].[K+].[CH:29]([N:32]=[C:33]=[O:34])([CH3:31])[CH3:30]>C1COCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:33]([NH:32][CH:29]([CH3:31])[CH3:30])=[O:34])[CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 61277Isopropyl isocyanateHCID 115439135-Amino-1-(4-fluorophenyl)4-[3-hydroxybenzoyl]pyrazole

Product 1

HCID 9929867HCID 9929867, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Amino-1-(4-fluorophenyl)-4-[3-hydroxybenzoyl]pyrazole, step 2, (0.30 g, 1.01 mmol) was combined with K2CO3 (0.418 g, 3.03 mmol) and THF (6 mL). The mixture was cooled in an ice bath and then isopropyl isocyanate (0.12 mL, 1.21 mmol) was added. The reaction was allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was quenched with water, extracted into ethyl acetate, dried (MgSO4), filtered, and concentrated to dryness. The residue was stirred in methanol and dichloromethane for one hour then filtered to give 0.118 g of 5-amino-1-(4-fluorophenyl)-4-[3-isopropylaminocarbonyloxybenzoyl]pyrazole (mpt. 225.2-230.1° C.).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customThe reaction mixture was quenched with water
  3. extractionextracted into ethyl acetate
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. stirringThe residue was stirred in methanol
  8. filtrationdichloromethane for one hour then filtered

Sources & evidence

ORD record
ord-96b02d93f378484598a9a64b7e6b5d91
Source dataset
uspto-grants-2005_12
Patent number
US06979693B2

Reaction notes

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