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 1707996Notes

Reaction equation

HRID 1707996 reaction equation
[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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-83c573fda8e14c758add9a402683ad20
Source dataset
uspto-grants-1994_10
Patent number
US05356894

Reaction notes

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