Dimethyl Sulfoxide → 8-(3-Aminoazepan-1-yl)-3-methyl-7-(2-trifluoromethylbenzyl)-3,7-dihydropurine-2,6-dione TFA

HRID 458639Notes

Reaction equation

HRID 458639 reaction equation
Br[C:2]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:20])[F:19])[C:9]2[C:8](=[O:22])[NH:7][C:6](=[O:23])[N:5]([CH3:24])[C:4]=2[N:3]=1.[NH:25]1[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]([NH2:32])[CH2:26]1.C(N(CC)CC)C.[OH2:40].CS(C)=[O:43]>ClCCl>[OH:40][C:13]([C:18]([F:21])([F:20])[F:19])=[O:43].[NH2:32][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][N:25]([C:2]2[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:18]([F:21])([F:19])[F:20])[C:9]3[C:8](=[O:22])[NH:7][C:6](=[O:23])[N:5]([CH3:24])[C:4]=3[N:3]=2)[CH2:26]1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8471TriethylamineHCID 2756445Azepan-3-amineHCID 225086498-Bromo-3-methyl-7-(2-trifluoromethylbenzyl)-3,7-dihydropurine-2,6-dione

Product 1

HCID 1317247998-(3-Aminoazepan-1-yl)-3-methyl-7-(2-trifluoromethylbenzyl)-3,7-dihydropurine-2,6-dione TFA

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

8-Bromo-3-methyl-7-(2-trifluoromethylbenzyl)-3,7-dihydropurine-2,6-dione (81A) (300 mg, 0.7 mmol) and azepan-3-ylamine (255 mg, 2,2 mmol), and triethylamine (0.5 ml, 3.7 mmol) were dissolved in 3 ml of DMSO and the mixture was subjected to microwaves (method F, 200° C., 300 W) for 10 minutes. To the reaction mixture was added 100 ml of water and 100 ml of dichloromethane, and the organic layer was washed with 1N NaOH, and dried over sodium sulfate. The solvents were evaporated and the crude product was purified by preparative HPLC (method A1, Rt=7.42 min.). Evaporation of the solvent afforded the title compound as a brown oil.

Workup

  1. washthe organic layer was washed with 1N NaOH
  2. dry with materialdried over sodium sulfate
  3. customThe solvents were evaporated
  4. customthe crude product was purified by preparative HPLC (method A1, Rt=7.42 min.)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5cbfa1b9329d467789a6ecafe5ce2d14
Source dataset
uspto-grants-2007_03
Patent number
US07192952B2

Reaction notes

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