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 1853096노트

반응식

HRID 1853096 반응식
[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

참가 물질

8

반응물 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

생성물 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-carboxamide수율 82.6%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

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.

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 Na2SO4
  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-335b95ccc5c94fd798393012b9a8b798
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962623B2

반응 노트

불러오는 중…