Dimethyl Sulfoxide → HCID 68831674, compound

HRID 227218Notes

Reaction equation

HRID 227218 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH:12]([CH2:44][O:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[CH2:13][N:14]1[C:23](=[O:24])[C:22]2[N:21]([CH2:25][C:26]#[C:27][CH3:28])[C:20]([N:29]3[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:30]3)=[N:19][C:18]=2[N:17]([CH3:43])[C:15]1=[O:16].C(N(CC)CC)C>C(Cl)Cl>[O:11]=[C:12]([CH2:44][O:45][C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)[CH2:13][N:14]1[C:23](=[O:24])[C:22]2[N:21]([CH2:25][C:26]#[C:27][CH3:28])[C:20]([N:29]3[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:40])[CH3:41])=[O:37])[CH2:30]3)=[N:19][C:18]=2[N:17]([CH3:43])[C:15]1=[O:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68828634HCID 68828634, compound

Product 1

HCID 68831674HCID 68831674, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

A solution of 107 μl dimethylsulphoxide in 0.5 ml methylene chloride is added dropwise to 64 μl oxalyl chloride in 2 ml methylene chloride with stirring at −60° C. After five minutes a solution of 345 mg of 1-(2-hydroxy-3-phenoxy-propyl)-3-methyl-7-(2-butyn-1-yl)-8-[3-(tert.-butyloxycarbonylamino)-piperidin-1-yl]-xanthine in 1.5 ml methylene chloride is added dropwise and after another 15 minutes 0.42 ml of triethylamine are added. Then the cooling bath is removed and the reaction mixture is allowed to warm up to ambient temperature. For working up it is diluted with methylene chloride and washed with water. The organic phase is dried over magnesium sulphate, evaporated down and chromatographed through a silica gel column with cyclohexane/ethyl acetate (4:1 to 1:1) as eluant.

Workup

  1. additionare added
  2. customThen the cooling bath is removed
  3. temperatureto warm up to ambient temperature
  4. additionis diluted with methylene chloride
  5. washwashed with water
  6. dry with materialThe organic phase is dried over magnesium sulphate
  7. customevaporated down
  8. customchromatographed through a silica gel column with cyclohexane/ethyl acetate (4:1 to 1:1) as eluant

Sources & evidence

ORD record
ord-6d49f448a98749328c541c89e9f59994
Source dataset
uspto-grants-2009_07
Patent number
US07560450B2

Reaction notes

Loading…