Diisopropylethylamine → N-((8-Fluoro-2-phenylquinolin-3-yl)methyl)-9H-purin-6-amine

HRID 216816

반응식

HRID 216816 반응식
Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C(N(C(C)C)CC)(C)C.[F:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:27]([CH2:37][NH2:38])=[CH:26]2>C(O)CCC>[F:20][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]2[C:30]=1[N:29]=[C:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:27]([CH2:37][NH:38][C:2]1[N:10]=[CH:9][N:8]=[C:7]3[C:3]=1[NH:4][CH:5]=[N:6]3)=[CH:26]2

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 5287830Purine, 6-bromo-HCID 57707794(8-Fluoro-2-phenylquinolin-3-yl)methanamine

생성물 1

HCID 25071603N-((8-Fluoro-2-phenylquinolin-3-yl)methyl)-9H-purin-6-amine

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
110 °C

실험 절차

To a reaction flask was added 6-bromopurine (19 mg, 95 μmol, 1.2 eq), diisopropylethylamine (42 μl, 238 μmol, 3 eq), (8-fluoro-2-phenylquinolin-3-yl)-methanamine (20 mg, 79 μmol, 1 eq), and n-butanol (0.75 mL). The reaction was heated to 110° C. for 8 h. The reaction was cooled to rt and the solvent was removed in vacuo. The compound was purified by reverse phase HPLC. The fractions were concentrated and freebased with sat. NaHCO3. The organic layer was extracted into DCM, dried over MgSO4, filtered, and concentrated to afford a white solid, N-((8-fluoro-2-phenylquinolin-3-yl)methyl)-7H-purin-6-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.35 (s, 1H), 8.31 (s, 1H), 7.90 (s, 1H), 7.68 (m, 2H), 7.45 (m, 6H), 6.78 (br s, 1H), 5.07 (br s, 2H). Mass Spectrum (ESI) m/e=370.9 (M+1).

후처리

  1. temperatureThe reaction was cooled to rt
  2. customthe solvent was removed in vacuo
  3. customThe compound was purified by reverse phase HPLC
  4. concentrationThe fractions were concentrated
  5. extractionThe organic layer was extracted into DCM
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3f3c7d630aae4cd484189a2d9ac4b468
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193199B2

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