Diisopropylethylamine → 1-(2-Hydroxy-2-methyl-propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid [4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-amide

HRID 1029173

반응식

HRID 1029173 반응식
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:16]=[CH:15][N:14]=[C:13]3[C:8]=2[C:9]2[CH:21]=[CH:20][CH:19]=[CH:18][C:10]=2[C:11](=[O:17])[NH:12]3)=[CH:4][CH:3]=1.[OH:24][C:25]([CH3:44])([CH3:43])[CH2:26][N:27]1[C:31]([CH3:32])=[C:30]([C:33](O)=[O:34])[C:29](=[O:36])[N:28]1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.CCN(C(C)C)C(C)C>O1CCOCC1.CCOC(C)=O.O>[O:17]=[C:11]1[C:10]2[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=2[C:8]2[C:13](=[N:14][CH:15]=[CH:16][C:7]=2[O:6][C:5]2[CH:22]=[CH:23][C:2]([NH:1][C:33]([C:30]3[C:29](=[O:36])[N:28]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[N:27]([CH2:26][C:25]([OH:24])([CH3:44])[CH3:43])[C:31]=3[CH3:32])=[O:34])=[CH:3][CH:4]=2)[NH:12]1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 533934301-(2-Hydroxy-2-methylpropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazole-4-carboxylic AcidHCID 581683671-(4-Amino-phenoxy)-5H-benzo[c][1,8]naphthyridin-6-one

생성물 1

HCID 581680681-(2-Hydroxy-2-methyl-propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid [4-(6-oxo-5,6-dihydro-benzo[c][1,8]naphthyridin-1-yloxy)-phenyl]-amide수율 30.4%

시약·촉매·용매 2

HCID 312751,4-Dioxane용매HCID 22728543Water ethylacetate용매

실험 절차

Compound 137 (50 mg, 0.16 mmol), 1-(2-hydroxy-2-methyl-propyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxylic acid (57 mg, 0.26 mmol), BOP-Cl (63 mg, 0.25 mmol), and DIEA (0.08 mL, 0.49 mmol) were suspended in dioxane (2 mL), and stirred overnight at room temperature. The reaction mixture was diluted with EtOAc/H2O, and filtered through an Extrelut column. The column was washed with EtOAc and the filtrate was concentrated. The crude material was purified via Biotage eluting with a gradient of 0 to 10% MeOH in CH2Cl2 to provide 209 (28 mg, 30% yield) as a white solid. LC-MS (M+H=576, obsd.=576).

후처리

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe crude material was purified via Biotage
  5. washeluting with a gradient of 0 to 10% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-b6429d7bb64d4c8cb1f7e92751897dc1
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08735584B2

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