Water → 1-[2-(2-Hydroxy-phenyl)-2-oxo-ethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-[3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-xanthine

HRID 633672Notes

Reaction equation

HRID 633672 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].[OH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:42])[CH2:23][N:24]1[C:33](=[O:34])[C:32]2[N:31]([CH2:35][CH:36]=[C:37]([CH3:39])[CH3:38])[C:30](Cl)=[N:29][C:28]=2[N:27]([CH3:41])[C:25]1=[O:26].C(=O)([O-])[O-].[Na+].[Na+].O>CS(C)=O>[OH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:42])[CH2:23][N:24]1[C:33](=[O:34])[C:32]2[N:31]([CH2:35][CH:36]=[C:37]([CH3:38])[CH3:39])[C:30]([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:29][C:28]=2[N:27]([CH3:41])[C:25]1=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 42330413-(Boc-amino)piperidineHCID 575145341-[2-(2-Hydroxy-phenyl)-2-oxo-ethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-chloro-xanthine

Product 1

HCID 667237361-[2-(2-Hydroxy-phenyl)-2-oxo-ethyl]-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
60 °C

Procedure

1.30 g of 3-tert.-butyloxycarbonylamino-piperidine are added to a mixture of 2.51 g of 1-[2-(2-hydroxy-phenyl)-2-oxo-ethyl]-3-methyl-7-(3-methyl-2-buten-1-yl)-8-chloro-xanthine and 880 mg of sodium carbonate in 8 ml of dimethylsulphoxide. The reaction mixture is stirred for 18 hours at 60° C. For working up it is combined with water and the precipitate formed is suction filtered. The solid crude product is dissolved in ethyl acetate, the solution is dried over magnesium sulphate and evaporated down. The flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (10:1 to 1:1) as eluant.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. dissolutionThe solid crude product is dissolved in ethyl acetate
  4. dry with materialthe solution is dried over magnesium sulphate
  5. customevaporated down
  6. customThe flask residue is chromatographed through a silica gel column with cyclohexane/ethyl acetate (10:1 to 1:1) as eluant

Sources & evidence

ORD record
ord-c48ba1d7c0ad4273ab8156db199e1727
Source dataset
uspto-grants-2016_04
Patent number
US09321791B2

Reaction notes

Loading…