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

HRID 1045711노트

반응식

HRID 1045711 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
20 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-8c715ad0d14443ceae3ea843dfd6a821
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569300B2

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