Diisopropylethylamine → HCID 25029197, compound

HRID 639475Notes

Reaction equation

HRID 639475 reaction equation
CS([O:5][CH2:6][CH2:7][N:8]1[C:16]2[N:15]=[C:14]([NH2:17])[N:13]3[N:18]=[C:19]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[C:12]3[C:11]=2[CH:10]=[CH:9]1)(=O)=O.[F:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1O.CCN(C(C)C)C(C)C>CN(C=O)C>[F:26][C:27]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=1[O:5][CH2:6][CH2:7][N:8]1[C:16]2[N:15]=[C:14]([NH2:17])[N:13]3[N:18]=[C:19]([C:21]4[O:22][CH:23]=[CH:24][CH:25]=4)[N:20]=[C:12]3[C:11]=2[CH:10]=[CH:9]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1230512,4-DifluorophenolHCID 866234642-{5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl}ethyl methanesulfonate

Product 1

HCID 25029197HCID 25029197, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of the title D compound of Example 1, 2-{5-amino-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-7-yl}ethyl methanesulfonate (0.06 g, 0.165 mmol) in dry DMF (5 mL), 2,4-difluorophenol (0.33 mmol) and 0.06 mL of DIEA are added, and the solution is stirred at 100° C. for 5 h. The reaction mixture is cooled to RT, and the solvent is removed under reduced pressure. To the residue, acetonitrile is added and the solution is stirred at 60° C. for 0.5 h. The solution is then cooled to RT, and the resulting solids are collected by filtration to give 7-(2-(2,4-difluorophenoxy)ethyl)-2-(furan-2-yl)-7H-pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine: LC/MS (M+1=397.1). 1H NMR (DM50-d6, 400 MHz) δ 4.41 (m, 2H), 4.53 (m, 2H), 6.63 (m, 1H), 6.72 (m, 1H), 6.99 (m, 1H), 7.23 (m, 4H), 7.55 (br s, 2H, NH2), 7.92 (s, 1H). Anal. calculated for (C19H14F2N6O2+0.5H2O): C, 56.30; H, 3.73; F, 9.37; N, 20.73; 0, 9.87. Found C, 56.36; H, 3.59; N, 18.51.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. customthe solvent is removed under reduced pressure
  3. additionTo the residue, acetonitrile is added
  4. stirringthe solution is stirred at 60° C. for 0.5 h
  5. temperatureThe solution is then cooled to RT
  6. filtrationthe resulting solids are collected by filtration

Sources & evidence

ORD record
ord-ac40d8d8bb0d449cbb8c4c2392313f46
Source dataset
uspto-grants-2010_04
Patent number
US07691869B2

Reaction notes

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