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 1853100노트

반응식

HRID 1853100 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8ebb55893eef41dbabafd0603d1e09d0
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962623B2

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