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

HRID 216816

反応式

HRID 216816 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3f3c7d630aae4cd484189a2d9ac4b468
出典データセット
uspto-grants-2012_06
特許番号
US08193199B2

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