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 1853100ノート

反応式

HRID 1853100 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8ebb55893eef41dbabafd0603d1e09d0
出典データセット
uspto-grants-2015_02
特許番号
US08962623B2

反応ノート

読み込み中…