2-Methoxy-6-(tributylstannyl)pyrazine → 6-(6-methoxypyrazin-2-yl)-8-(4-morpholinophenylamino)-2,7-naphthyridin-1(2H)-one

HRID 1034946ノート

反応式

HRID 1034946 の反応式
Cl[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:15][CH:14]=3)[N:11]=1)[C:8](=[O:25])[NH:7][CH:6]=[CH:5]2.[CH3:26][O:27][C:28]1[CH:33]=[N:32][CH:31]=[C:30]([Sn](CCCC)(CCCC)CCCC)[N:29]=1>CN(C=O)C>[CH3:26][O:27][C:28]1[N:29]=[C:30]([C:2]2[CH:3]=[C:4]3[C:9](=[C:10]([NH:12][C:13]4[CH:18]=[CH:17][C:16]([N:19]5[CH2:24][CH2:23][O:22][CH2:21][CH2:20]5)=[CH:15][CH:14]=4)[N:11]=2)[C:8](=[O:25])[NH:7][CH:6]=[CH:5]3)[CH:31]=[N:32][CH:33]=1

参加物

4

反応物 2

HCID 164271032-Methoxy-6-(tributylstannyl)pyrazineHCID 866495446-chloro-8-(4-morpholinophenylamino)-2,7-naphthyridin-1(2H)-one

生成物 1

HCID 580941186-(6-methoxypyrazin-2-yl)-8-(4-morpholinophenylamino)-2,7-naphthyridin-1(2H)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

6-chloro-8-(4-morpholinophenylamino)-2,7-naphthyridin-1(2H)-one (30 mg, 0.084 mmol) was dissolved in DMF (1 mL) in a microwave vial and 2-methoxy-6-(tributylstannyl)pyrazine (40 mg, 0.1 mmol) was added followed by PdCl2dppf (6.1 mg, 0.0084 mmol) at room temperature. The vial was flushed with nitrogen and closed the cap and subjected to microwave irradiation at 135 C for 60 minutes. The reaction mixture was diluted with DMSO and purified by prep HPLC. The compound was isolated as a TFA salt. 1H NMR (400 MHz, DMSO-d6) δ 11.14 (s, 1H), 8.96 (s, 1H), 8.33 (s, 1H), 7.68 (s, 1H), 7.67 (d, 2H, J=8.8 Hz), 7.38 (m, 1H), 6.95 (d, 2H, J=8.8 Hz), 6.57 (d, 1H, J=7.2 Hz), 4.0 (s, 3H), 3.69 (t, 4H, J=4.8 Hz), 3.04 (t, 4H, J=4.8 Hz); MS m/z 431.2 (M+1).

後処理

  1. additionwas added
  2. customThe vial was flushed with nitrogen
  3. customclosed the
  4. customcap
  5. customirradiation at 135 C for 60 minutes
  6. additionThe reaction mixture was diluted with DMSO
  7. custompurified by prep HPLC

出典と根拠

ORDレコード
ord-12bbe4ab827b4a8a904d18d2a773b3d3
出典データセット
uspto-grants-2013_10
特許番号
US08546370B2

反応ノート

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