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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Water → N4-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-N6-methyl-1H-pyrazolo[3,4-b]pyridine-4,6-dicarboxamide

HRID 1854058
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HRID 1854058 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[CH:19]=[C:18]([C:20](O)=[O:21])[N:17]=[C:16]2[N:23]([CH:26]([CH3:28])[CH3:27])[N:24]=[CH:25][C:15]=12)=[O:13].CN.C1C[N:34]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:33]C1.F[P-](F)(F)(F)(F)F.O>CS(C)=O.CO.C(Cl)Cl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[NH:5][C:4](=[O:9])[C:3]=1[CH2:10][NH:11][C:12]([C:14]1[C:15]2[CH:25]=[N:24][N:23]([CH:26]([CH3:27])[CH3:28])[C:16]=2[N:17]=[C:18]([C:20]([NH:34][CH3:33])=[O:21])[CH:19]=1)=[O:13]
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참가 물질

7

반응물 4

HCID 962WaterHCID 6329MethylamineHCID 2724699PyBOPHCID 683512284-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylic acid

생성물 1

HCID 68295268N4-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-N6-methyl-1H-pyrazolo[3,4-b]pyridine-4,6-dicarboxamide수율 8%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 21226129Dichloromethane methanol용매

실험 절차

4-(((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)carbamoyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-6-carboxylic acid (1 equiv.) was dissolved in DMSO and methylamine (2 equiv.) was added to it. The reaction mixture was stirred at room temperature for 15 min before PYBOP (1.5 equiv.) was added to it and stirring was continued overnight. After completion of the reaction, water was added to it and extraction was carried out using 20% MeOH/DCM. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography/prep. HPLC to give the desired compound (8% yield). LCMS: 397.15 (M+1)+; HPLC: 93.04% (@ 254 nm) (Rt; 5.597); 1H NMR (DMSO-d6, 400 MHz) δ 11.53 (s, 1H), 9.04 (t, 1H, J=4.4 Hz), 8.95 (d, 1H, J=4.8 Hz), 8.43 (s, 1H), 8.17 (s, 1H), 5.88 (s, 1H), 5.49-5.43 (m, 1H), 4.36 (d, 2H, J=4.8 Hz), 2.88 (d, 3H, J=4.4 Hz), 2.21 (s, 3H), 2.12 (s, 3H), 1.52 (d, 6H, J=6.8 Hz).

후처리

  1. additionwas added to it
  2. additionwas added to it and extraction
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude material which
  8. customwas purified by column chromatography/prep

출처 및 근거

ORD 기록
ord-4f5c25de52fb49cb9d3b2ad710d9c341
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08962620B2

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