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

HRID 930048Notes

Reaction equation

HRID 930048 reaction equation
C(N(CC)C(C)C)(C)C.[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[N:22]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[N:21]=[C:20]([C:29]([OH:31])=O)[CH:19]=2)[CH:14]=[C:15]([F:17])[CH:16]=1.[O:32]=[C:33]1[CH2:38][NH:37][CH2:36][CH2:35][NH:34]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]([C:18]2[N:22]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[N:21]=[C:20]([C:29]([N:37]3[CH2:36][CH2:35][NH:34][C:33](=[O:32])[CH2:38]3)=[O:31])[CH:19]=2)[CH:14]=[C:15]([F:17])[CH:16]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 89602438HCID 89602438, compound

Product 1

HCID 715765334-[5-(3-Chloro-5-fluoro-phenyl)-1-(3-pyridyl)pyrazole-3-carbonyl]piperazin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.07 ml (0.43 mmol) of N,N-diisopropylethylamine is added to a solution of 75 mg (0.21 mmol, 90% purity) of the compound of Example 22A, 23 mg (0.23 mmol) of 2-oxopiperazine, and 113 mg (0.30 mmol) of HATU in 2 ml of THF, and the mixture that is obtained is stirred for 3 hours at room temperature. The reaction mixture is separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient), and the title compound is obtained in a quantitative yield (87 mg).

Workup

  1. customthe mixture that is obtained
  2. customThe reaction mixture is separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-18e289a9e3ac419889cece7242c2fdaa
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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