6-Chloropurine → HCID 178463552、化合物

HRID 1192692ノート

反応式

HRID 1192692 の反応式
[F:1][C:2]1[CH:11]=[C:10]([CH:12]([NH2:14])[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl[C:23]1[N:31]=[CH:30][N:29]=[C:28]2[C:24]=1[NH:25][CH:26]=[N:27]2.[Na]>C(O)CCC>[F:1][C:2]1[CH:11]=[C:10]([CH:12]([NH:14][C:23]2[N:31]=[CH:30][N:29]=[C:28]3[C:24]=2[N:25]=[CH:26][NH:27]3)[CH3:13])[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[CH:16]=2)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

参加物

5

反応物 3

HCID 53592776-ChloropurineHCID 5360545SodiumHCID 583685621-[5-Fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine

生成物 1

HCID 178463552HCID 178463552、化合物

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
110 °C

実験手順

A mixture of 1-[5-fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethanamine (0.39 g, 1.4 mmol, 6-chloropurine (0.27 g, 1.8 mmol) and sodium hydrogenecarbonate (0.17 g, 2.0 mmol) in 1-butanol (4 mL) was heated at 110° C. overnight. The mixture was filtered and purified on a preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min) to give the desired product. LCMS calculated for C22H17F2N6 (M+H)+: m/z=403.1; Found: 403.1. The racemic N-{1-[5-fluoro-8-(3-fluorophenyl)quinolin-7-yl]ethyl}-9H-purin-6-amine (70 mg, 0.2 mmol) was submitted for chiral resolution (column: ChiralPak IA, 20×250 mm, 5 μm; mobile phase: 15% ethanol/85% hexanes; flow rate: 15 mL/min) to give two enantiomers. retention times: 8.7 and 13.5 minutes, respectively.

後処理

  1. filtrationThe mixture was filtered
  2. custompurified on a preparative LCMS (XBridge C18 column
  3. washeluting with a gradient of acetonitrile in water with 0.2% ammonium hydroxide, at a flow rate of 30 mL/min)

出典と根拠

ORDレコード
ord-532a6b7a0048461089d78392c702f95f
出典データセット
uspto-grants-2014_03
特許番号
US08680108B2

反応ノート

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