Water → 1-[2-(2-Nitrophenyl)-2-oxoethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-[3-(tert-butyloxycarbonylamino)piperidin-1-yl]xanthine

HRID 1174566Notes

Reaction equation

HRID 1174566 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24](=[O:44])[CH2:25][N:26]1[C:35](=[O:36])[C:34]2[N:33]([CH2:37][CH:38]=[C:39]([CH3:41])[CH3:40])[C:32](Cl)=[N:31][C:30]=2[N:29]([CH3:43])[C:27]1=[O:28])([O-:17])=[O:16].C(=O)([O-])[O-].[Na+].[Na+].O>CS(C)=O>[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24](=[O:44])[CH2:25][N:26]1[C:35](=[O:36])[C:34]2[N:33]([CH2:37][CH:38]=[C:39]([CH3:40])[CH3:41])[C:32]([N:11]3[CH2:12][CH2:13][CH2:14][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10]3)=[N:31][C:30]=2[N:29]([CH3:43])[C:27]1=[O:28])([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 42330413-(Boc-amino)piperidineHCID 179648741-[2-(2-Nitrophenyl)-2-oxoethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-chloroxanthine

Product 1

HCID 179648581-[2-(2-Nitrophenyl)-2-oxoethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-[3-(tert-butyloxycarbonylamino)piperidin-1-yl]xanthine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

2.20 g of 3-tert-butyloxycarbonylaminopiperidine is added at 65° C. to 4.40 g of 1-[2-(2-nitrophenyl)-2-oxoethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-chloroxanthine and 1.30 g of sodium carbonate in 50 mL of dimethylsulfoxide. The reaction mixture is stirred for approximately 16 hours at 65° C. After cooling to ambient temperature, it is poured onto a mixture of 600 mL of water and 100 g of ice. The precipitate formed is suction filtered and washed with water. The filter cake is dissolved in diethyl ether, and the solution is dried and evaporated down. The brown resinous flask residue is brought to crystallization with diisopropylether. Yield: 3.30 g (54% of theory); Rf value: 0.52 (silica gel, cyclohexane/ethyl acetate (3:7)); mass spectrum (ESI+): m/z=596 [M+H]+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customThe precipitate formed
  3. filtrationfiltered
  4. washwashed with water
  5. dissolutionThe filter cake is dissolved in diethyl ether
  6. customthe solution is dried
  7. customevaporated down
  8. customThe brown resinous flask residue is brought to crystallization with diisopropylether

Sources & evidence

ORD record
ord-583b4360887d44cf8c25ceee058b3493
Source dataset
uspto-grants-2010_11
Patent number
US07838529B2

Reaction notes

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