Formaldehyde → 5-(Furan-3-yl)-8-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[4,3-a]pyrazine

HRID 1045711ノート

反応式

HRID 1045711 の反応式
Cl.[O:2]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]3[CH:13]=[N:14][N:15]=[C:11]3[C:10]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)=[N:9][CH:8]=2)=[CH:3]1.C=O.Cl[CH2:25]Cl.C([BH3-])#N.[Na+]>CO>[O:2]1[CH:6]=[CH:5][C:4]([C:7]2[N:12]3[CH:13]=[N:14][N:15]=[C:11]3[C:10]([N:16]3[CH2:17][CH2:18][N:19]([CH3:25])[CH2:20][CH2:21]3)=[N:9][CH:8]=2)=[CH:3]1

参加物

6

反応物 4

HCID 712FormaldehydeHCID 6344DichloromethaneHCID 5003444Sodium cyanoborohydrideHCID 673948055-(furan-3-yl)-8-(piperazin-1-yl)-[1,2,4]triazolo[4,3-a]pyrazine HCl salt

生成物 1

HCID 533910905-(Furan-3-yl)-8-(4-methylpiperazin-1-yl)-[1,2,4]triazolo[4,3-a]pyrazine収率 49%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
20 °C

実験手順

A 50 mL round bottom flask was charged with 5-(furan-3-yl)-8-(piperazin-1-yl)-[1,2,4]triazolo[4,3-a]pyrazine HCl salt (350 mg, 1.14 mmol), 40% aqueous formaldehyde (20 mL), dichloromethane (20 mL), methanol (20 mL) and sodium cyanoborohydride (245 mg, 3.90 mmol) at 0° C. The resulting mixture was stirred at 20° C. overnight. It was then concentrated in vacuo and the residue was extracted with dichloromethane. The organic layer was washed with brine (10 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was re-crystallized from a 1/5 (v/v) dichloromethane/ethyl ether, to afford 0.16 g (49%) of the product as a yellow solid. 1H NMR (300 MHz, CDCl3) δ: 8.83 (s, 1H), 7.76 (dd, J=1.5, 0.9 Hz, 1H), 7.62 (dd, J=1.8, 1.5 Hz, 1H), 7.36 (s, 1H), 6.68 (dd, J=1.8, 0.9 Hz, 1H), 4.41 (br, 4H), 2.59 (t, J=5.1 Hz, 4H), 2.36 (s, 3H). MS m/z: 285 (M+H+).

後処理

  1. concentrationIt was then concentrated in vacuo
  2. extractionthe residue was extracted with dichloromethane
  3. washThe organic layer was washed with brine (10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was re-crystallized from a 1/5 (v/v) dichloromethane/ethyl ether

出典と根拠

ORDレコード
ord-8c715ad0d14443ceae3ea843dfd6a821
出典データセット
uspto-grants-2013_10
特許番号
US08569300B2

反応ノート

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