Trifluoroacetic acid → 7-Amino-2-(2-furyl)-5-[2-(4-pivaloyloxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine

HRID 1707996

반응식

HRID 1707996 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.FC(F)(F)C(O)=O.[C:33](Cl)(=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35]>ClCCl>[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:20]=[CH:21][C:22]([O:25][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:23][CH:24]=2)[N:3]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 62493Pivaloyl chlorideHCID 1764074-(2-(7-Amino-2-(2-furyl)-(1,2,4)triazolo(2,3-a)-(1,3,5)triazin-5-yl-amino)ethyl)phenol

생성물 1

HCID 157300227-Amino-2-(2-furyl)-5-[2-(4-pivaloyloxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

7-Amino-2-(2-furyl)-5-[2-(4-hydroxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine (1 g, prepared as described in Example 81) was suspended in dichloromethane (20 ml) and trifluoroacetic acid (20 ml) was added with stirring. Pivaloyl chloride (0.4 ml) was added dropwise at ambient temperature. The mixture was stirred for 2 hours and then the dichloromethane and trifluoroacetic acid was removed in vacuo. The residue was purified by chromatography on silica (100 g) eluting with dichloromethane containing methanol (5.0% v/v). The solid obtained (1.2 g) was crystallised from toluene and finally from isopropanol (25 ml) to give 7-amino-2-(2-furyl)-5-[2-(4-pivaloyloxyphenyl)ethyl]amino[1,2,4]-triazolo[1,5-a][1,3,5]triazine as a solid; m.p. 208°-210° C.; microanalysis, found: C, 59.6; H, 6.1; N, 21.7%; C21H24N7O3 0.5 C3H7OH requires C, 59.9; H, 6.0; N, 21.7%; NMR 1.06(d, ca 3H, (CH3)2CHOH), 1.3(s, 9H, CH3C), 2.9(t, 2H, CH2Ar), 3.55 (t, 2H, CH2N), 3.80(heptet, ca 0.5 H, (CH3)2CHOH), 6.68(dd, 1H, furyl-4H), 7.01 and 7.30 (A2B2 pattern, 4H, phenyl-H), 7.08 (d, 1H, furyl-3H) and 7.82(d, 1H, furyl-5H); m/e 422 (M+H)+.

후처리

  1. stirringThe mixture was stirred for 2 hours
  2. customthe dichloromethane and trifluoroacetic acid was removed in vacuo
  3. customThe residue was purified by chromatography on silica (100 g)
  4. washeluting with dichloromethane
  5. additioncontaining methanol (5.0% v/v)
  6. customThe solid obtained (1.2 g)
  7. customwas crystallised from toluene and finally from isopropanol (25 ml)

출처 및 근거

ORD 기록
ord-83c573fda8e14c758add9a402683ad20
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05356894

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