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

HRID 930106Notes

Reaction equation

HRID 930106 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]([O:29][CH3:30])[CH:28]=3)=[CH:21][C:20]([C:31]([OH:33])=O)=[N:19]2)[CH:14]=[CH:15][C:16]=1[F:17].Cl.[NH:35]1[CH:39]=[CH:38][NH:37][C:36]1=O.CN(C([O:48]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.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]([O:29][CH3:30])[CH:28]=3)=[CH:21][C:20]([C:31]([N:35]3[CH2:39][C:38](=[O:48])[NH:37][CH2:36]3)=[O:33])=[N:19]2)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 66687731HCID 66687731, compound2×HCID 896024571-(3-Chloro-4-fluorophenyl)-5-(5-methoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 865743071-[1-(3-Chloro-4-fluoro-phenyl)-5-(5-methoxy-3-pyridyl)pyrazole-3-carbonyl]imidazolidin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.12 ml (0.70 mmol) of N,N-diisopropylethylamine is added to a solution of 220 mg (0.23 mmol, 37% purity) of the compound of Example 64A, 57 mg (0.47 mmol) of 4-imidazolinone-hydrochloride, and 142 mg (0.38 mmol) of HATU in 6 ml of THF, and the mixture that is obtained is stirred for 20 hours at room temperature. After the further addition of 57 mg (0.47 mmol) of 4-imidazolinone-hydrochloride as well as 89 mg (0.23 mmol) of HATU, stirring is continued for 16 hours at 60° C. The crude product is separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient). 39 mg (35% of theory, 88% purity) of the title compound is obtained.

Workup

  1. customthe mixture that is obtained
  2. stirringstirring
  3. waitis continued for 16 hours at 60° C
  4. customThe crude product is separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-ca77122bd8e942f8ad3710f0250277fe
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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