Potassium Carbonate → HCID 9929867, compound

HRID 1278883Notes

Reaction equation

HRID 1278883 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, from Example 10, 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-61ea2320bfc348c781b8ff259c68d762
Source dataset
uspto-grants-2002_09
Patent number
US06444696B1

Reaction notes

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