Diisopropylethylamine → 1-[1-(3-Chloro-4-fluoro-phenyl)-5-(5-fluoro-3-pyridyl)pyrazole-3-carbonyl]imidazolidin-4-one

HRID 930102Notes

Reaction equation

HRID 930102 reaction equation
C(N(CC)C(C)C)(C)C.[Cl:10][C:11]1[CH:12]=[C:13]([N:18]2[C:22]([C:23]3[CH:24]=[N:25][CH:26]=[C:27]([F:29])[CH:28]=3)=[CH:21][C:20]([C:30]([OH:32])=O)=[N:19]2)[CH:14]=[CH:15][C:16]=1[F:17].Cl.[NH:34]1[CH:38]=[CH:37][NH:36][C:35]1=O.C1CN([P+]([O:56]N2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C1COCC1>[Cl:10][C:11]1[CH:12]=[C:13]([N:18]2[C:22]([C:23]3[CH:24]=[N:25][CH:26]=[C:27]([F:29])[CH:28]=3)=[CH:21][C:20]([C:30]([N:34]3[CH2:38][C:37](=[O:56])[NH:36][CH2:35]3)=[O:32])=[N:19]2)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 66687731HCID 66687731, compoundHCID 896099591-(3-Chloro-4-fluorophenyl)-5-(5-fluoropyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 865742911-[1-(3-Chloro-4-fluoro-phenyl)-5-(5-fluoro-3-pyridyl)pyrazole-3-carbonyl]imidazolidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.16 ml (0.89 mmol) of N,N-diisopropylethylamine is added to a solution of 100 mg (0.30 mmol) of the compound of Example 60A, 40 mg (0.33 mmol) of 4-imidazolinone-hydrochloride, and 217 mg (0.42 mmol) of PYBOP in 2 ml of THF, and the mixture that is obtained is stirred for 16 hours at room temperature. The reaction mixture is concentrated by evaporation in a vacuum. The residue is diluted with acetonitrile, filtered over a Millipore spray filter, and separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient). Solvent is removed from the product-containing fractions in a rotary evaporator, and the residue is recrystallized from acetonitrile. 96 mg (80% of theory) of the title compound is obtained.

Workup

  1. customthe mixture that is obtained
  2. concentrationThe reaction mixture is concentrated by evaporation in a vacuum
  3. additionThe residue is diluted with acetonitrile
  4. filtrationfiltered over a Millipore spray
  5. filtrationfilter
  6. customseparated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient)
  7. customSolvent is removed from the product-containing fractions in a rotary evaporator
  8. customthe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-6e02f97f449c4f61bd3dcb7f724fef29
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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