Diisopropylethylamine → 4-[1-(3-Chloro-4-fluoro-phenyl)-5-(5-methoxy-3-pyridyl)pyrazole-3-carbonyl]piperazin-2-one

HRID 930107Notes

Reaction equation

HRID 930107 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](O)=[O:32])=[N:19]2)[CH:14]=[CH:15][C:16]=1[F:17].[O:34]=[C:35]1[CH2:40][NH:39][CH2:38][CH2:37][NH:36]1.CN(C(ON1N=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:39]3[CH2:38][CH2:37][NH:36][C:35](=[O:34])[CH2:40]3)=[O:32])=[N:19]2)[CH:14]=[CH:15][C:16]=1[F:17]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-one2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 896024571-(3-Chloro-4-fluorophenyl)-5-(5-methoxypyridin-3-yl)-1H-pyrazole-3-carboxylic acid

Product 1

HCID 865743084-[1-(3-Chloro-4-fluoro-phenyl)-5-(5-methoxy-3-pyridyl)pyrazole-3-carbonyl]piperazin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.06 ml (0.32 mmol) of N,N-diisopropylethylamine is added to a solution of 150 mg (0.16 mmol, 37% purity) of the compound of Example 64A, 32 mg (0.32 mmol) of 2-oxopiperazine, and 97 mg (0.26 mmol) of HATU in 5 ml of THF, and the mixture that is obtained is stirred for 20 hours at room temperature. After the further addition of 32 mg (0.32 mmol) of 2-oxopiperazine, stirring is continued for 5 hours at 60° C. The crude product is separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient). The title compound is obtained in a quantitative yield.

Workup

  1. customthe mixture that is obtained
  2. stirringstirring
  3. waitis continued for 5 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-b415216b6a694a4eb80047419c316256
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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