Water → HCID 12093240, compound

HRID 1454941Notes

Reaction equation

HRID 1454941 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([N:11]3[CH2:16][CH2:15][CH2:14][CH:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:12]3)[N:7]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[C:6]=2[C:5](=[O:30])[NH:4][C:3]1=[O:31].Br[C:33]1[C:34]2[CH:46]=[CH:45][CH:44]=[CH:43][C:35]=2[N:36]([CH3:42])[S:37](=[O:41])(=[O:40])[C:38]=1C.[C:47](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH3:42][N:36]1[C:35]2[CH:43]=[CH:44][CH:45]=[CH:46][C:34]=2[C:33]([CH2:47][N:4]2[C:5](=[O:30])[C:6]3[N:7]([CH2:25][CH:26]=[C:27]([CH3:29])[CH3:28])[C:8]([N:11]4[CH2:16][CH2:15][CH2:14][CH:13]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[CH2:12]4)=[N:9][C:10]=3[N:2]([CH3:1])[C:3]2=[O:31])=[CH:38][S:37]1(=[O:40])=[O:41]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 66753597HCID 66753597, compoundHCID 68601695HCID 68601695, compound

Product 1

HCID 12093240HCID 12093240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 260 mg of 3-methyl-7-(3-methyl-2-buten-1-yl)-8-[3-(tert.-butyloxy-carbonylamino)-piperidin-1-yl]-xanthine, 185 mg of 4-bromo-methyl-1-methyl-1H-benzo[c][1,2]thiazine-2,2-dioxide and 550 mg of potassium carbonate in 4 ml N,N-dimethylformamide is stirred for about 40 h at ambient temperature. As no reaction of any note can be detected by thin layer chromatography, the mixture is heated to 60° C. for 2 h and then stirred for another 15 h at 50° C. until the reaction is virtually complete. Then 30 ml of water are added, the precipitate formed is suction filtered and dried. The crude product is purified by chromatography over a silica gel column with petroleum ether/ethyl acetate (1:1) as eluant.

Workup

  1. customAs no reaction of any note
  2. temperaturethe mixture is heated to 60° C. for 2 h
  3. stirringstirred for another 15 h at 50° C. until the reaction
  4. customthe precipitate formed
  5. filtrationfiltered
  6. customdried
  7. customThe crude product is purified by chromatography over a silica gel column with petroleum ether/ethyl acetate (1:1) as eluant

Sources & evidence

ORD record
ord-ab055c6bcf534916bdb577dbacfe543a
Source dataset
uspto-grants-2009_01
Patent number
US07482337B2

Reaction notes

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