Diisopropylethylamine → N-(4-{3-amino-6-[2-(4-morpholinyl)-4-pyridinyl]-2-pyrazinyl}phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

HRID 1853096ノート

反応式

HRID 1853096 の反応式
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([C:8]([OH:10])=O)[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:51][C:52]1[CH:57]=[CH:56][C:55]([C:58]2[C:59]([NH2:76])=[N:60][CH:61]=[C:62]([C:64]3[CH:69]=[CH:68][N:67]=[C:66]([N:70]4[CH2:75][CH2:74][O:73][CH2:72][CH2:71]4)[CH:65]=3)[N:63]=2)=[CH:54][CH:53]=1>C(Cl)Cl.CN(C=O)C.O>[NH2:76][C:59]1[C:58]([C:55]2[CH:56]=[CH:57][C:52]([NH:51][C:8]([C:5]3[C:4](=[O:11])[N:3]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[N:2]([CH3:1])[C:6]=3[CH3:7])=[O:10])=[CH:53][CH:54]=2)=[N:63][C:62]([C:64]2[CH:69]=[CH:68][N:67]=[C:66]([N:70]3[CH2:75][CH2:74][O:73][CH2:72][CH2:71]3)[CH:65]=2)=[CH:61][N:60]=1

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 246564Antipyric acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 682888223-(4-Aminophenyl)-5-[2-(4-morpholinyl)-4-pyridinyl]-2-pyrazinamine

生成物 1

HCID 68289162N-(4-{3-amino-6-[2-(4-morpholinyl)-4-pyridinyl]-2-pyrazinyl}phenyl)-1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide収率 82.6%

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 compound prepared in Example 1 (0.100 g) in 5 mL of DCM, 1.0 mL of DMF and N,N-diisopropylethylamine (DIEA) (0.072 g) was added the HATU (0.164 g) and stirred for 30 minutes. To the activated ester was added the compound prepared in Example 13 (0.15 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 Na2SO4. 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 (0.2 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 Na2SO4
  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-335b95ccc5c94fd798393012b9a8b798
出典データセット
uspto-grants-2015_02
特許番号
US08962623B2

反応ノート

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