1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-Amino-5-[4-(2-[7-amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino]ethyl)phenoxy]-2-(2-furyl)[1,2,4]triazolo[1,5-a][1,3,5]triazine

HRID 5819

반응식

HRID 5819 반응식
[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[N:5]=[C:4]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[N:3]=1.N12CCCN=C1CCCCC2.[NH2:37][C:38]1[N:43]2[N:44]=[C:45]([C:47]3[O:48][CH:49]=[CH:50][CH:51]=3)[N:46]=[C:42]2[N:41]=[C:40](S(C)(=O)=O)[N:39]=1.C(Cl)Cl.CO>C(#N)C>[NH2:37][C:38]1[N:43]2[N:44]=[C:45]([C:47]3[O:48][CH:49]=[CH:50][CH:51]=3)[N:46]=[C:42]2[N:41]=[C:40]([O:25][C:22]2[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][NH:16][C:4]3[N:3]=[C:2]([NH2:1])[N:7]4[N:8]=[C:9]([C:11]5[O:12][CH:13]=[CH:14][CH:15]=5)[N:10]=[C:6]4[N:5]=3)=[CH:24][CH:23]=2)[N:39]=1

참가 물질

6

반응물 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1764074-(2-(7-Amino-2-(2-furyl)-(1,2,4)triazolo(2,3-a)-(1,3,5)triazin-5-yl-amino)ethyl)phenolHCID 99708822-(Furan-2-yl)-5-(methylsulfonyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-7-amineHCID 21226129Dichloromethane methanol

생성물 1

HCID 98718987-Amino-5-[4-(2-[7-amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino]ethyl)phenoxy]-2-(2-furyl)[1,2,4]triazolo[1,5-a][1,3,5]triazine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

7-amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine (0.91 g) and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU, 0.37 ml) were added to a suspension of 7-amino-2-(2-furyl)-5-methylsulphonyl-[1,2,4]triazolo[1,5-a][1,3,5]triazine (0.82 g) in acetonitrile (50 ml) and the resulting mixture was heated under reflux for 17 hours, after which time thin layer chromatography (TLC) analysis on silica plates (eluent: methylene chloride-methanol 19:1 v/v) indicated that no methanesulphonyl starting material remained. The solvent was then evaporated and the residue was purified by column chromatography on silica (75 g) eluting with ethyl acetate-methylene chloride 7:3 v/v. A white solid was obtained, and this was crystallised from isopropanol to afford 7-amino-5-[4-(2-[7-amino-2-(2-furyl)-[1,2,4]triazolo[1,5-a][1,3,5]triazin-5-ylamino]ethyl)phenoxy]-2-(2-furyl)[ 1,2,4]triazolo[1,5-a][1,3,5]triazine, m.p. 285°-289° C.; microanalysis, found: C, 54.1; H, 4.4; N, 30.8%; C24H19N13O3 1.0(C3H7OH) requires: C, 54.2; H, 4.5; N, 30.5%; NMR: 2.92 (t, 2H, phenyl-CH2), 3.55 (q, 2H, CH2-N), 6.67 (m, 2H, 2 furyl-4H), 7.0 (d, 1H, furyl-3H), 7.11 (d, 1H, furyl-3'H), 7.16 and 7.35 (A2B2 pattern, 4H, phenyl-H), 7.5 (br t, 1H, NH rotamers), 7.85 (d, 1H, furyl-5H), 7.89 (d, 1H, furyl-5'H), 8.12 (br s, 2H, NH2) and 8.93 (d, 2H, NH2); m/e (M+H)+ 538.

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 17 hours
  3. customThe solvent was then evaporated
  4. customthe residue was purified by column chromatography on silica (75 g)
  5. washeluting with ethyl acetate-methylene chloride 7:3 v/v
  6. customA white solid was obtained
  7. customthis was crystallised from isopropanol

출처 및 근거

ORD 기록
ord-a3390456313144aa978257dac6d1ec7e
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246932

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