Antipyric acid → N-(4-(2-amino-5-bromopyridin-3-yl)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 1853100Notes

Reaction equation

HRID 1853100 reaction equation
[CH3:1][C:2]1[N:7]([CH3:8])[N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:4](=[O:5])[C:3]=1[C:15]([OH:17])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:42][C:43]1[CH:48]=[CH:47][C:46]([C:49]2[C:50]([NH2:56])=[N:51][CH:52]=[C:53]([Br:55])[CH:54]=2)=[CH:45][CH:44]=1>C(Cl)Cl.CN(C=O)C.O>[NH2:56][C:50]1[C:49]([C:46]2[CH:45]=[CH:44][C:43]([NH:42][C:15]([C:3]3[C:4](=[O:5])[N:6]([C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=4)[N:7]([CH3:8])[C:2]=3[CH3:1])=[O:17])=[CH:48][CH:47]=2)=[CH:54][C:53]([Br:55])=[CH:52][N:51]=1

Participants

7

Reactant 3

HCID 246564Antipyric acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 682889763-(4-Aminophenyl)-5-bromopyridin-2-amine

Product 1

HCID 68288995N-(4-(2-amino-5-bromopyridin-3-yl)phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamideYield 89.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To the antipyric acid (0.163 g) in 5 mL of DCM, 0.5 mL of DMF and TEA (1.4 mmol) was added the HATU (0.266 g) and stirred for 30 minutes. To the activated ester was added the compound prepared in Example 43 (0.185 g) and stirred for 1 hour. The reaction mixture was diluted with water, extracted with additional DCM, and the organic layer was washed with water, brine and dried over anhydrous sodium sulfate. The DCM layer was filtered and concentrated, and the crude was chromatographed on silica gel using 10:1 DCM:MeOH to give the title compound (0.3 g) having the following physical data.

Workup

  1. stirringstirred for 1 hour
  2. extractionextracted with additional DCM
  3. washthe organic layer was washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe DCM layer was filtered
  6. concentrationconcentrated
  7. customthe crude was chromatographed on silica gel using 10:1 DCM

Sources & evidence

ORD record
ord-8ebb55893eef41dbabafd0603d1e09d0
Source dataset
uspto-grants-2015_02
Patent number
US08962623B2

Reaction notes

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