Dimethyl Sulfoxide → HCID 59846317, compound

HRID 1363207Notes

Reaction equation

HRID 1363207 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1([C:20]2[N:28]=[C:27]3[C:23]([N:24]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:25](=[O:36])[N:26]3[C@H:29]3[CH2:34][CH2:33][C@H:32]([OH:35])[CH2:31][CH2:30]3)=[CH:22][N:21]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:12]1.C(N(CC)CC)C>C(Cl)Cl>[N:11]1([C:20]2[N:28]=[C:27]3[C:23]([N:24]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:25](=[O:36])[N:26]3[CH:29]3[CH2:30][CH2:31][C:32](=[O:35])[CH2:33][CH2:34]3)=[CH:22][N:21]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[CH:12]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178452558HCID 178452558, compound

Product 1

HCID 59846317HCID 59846317, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of oxalyl chloride (6.4 mg) in DCM (0.5 ml) was cooled to −60° C. and treated with a solution of DMSO (8 mg) in DCM (0.5 ml). The reaction mixture was stirred for 2 minutes, then treated with a solution of tert-butyl 2-(1H-benzo[d]imidazol-1-yl)-9-(trans-4-hydroxycyclohexyl)-8-oxo-8,9-dihydropurine-7-carboxylate (4 mg) in DCM (0.5 ml). After 15 minutes, triethylamine (0.4 mL) was added and the mixture was stirred at room temperature for 30 minutes. The mixture was diluted with 10 mL DCM and washed with 15 mL of water. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography to provide 2.3 mg of tert-butyl 2-(1H-benzo[d]imidazol-1-yl)-8-oxo-9-(4-oxocyclohexyl)-8,9-dihydropurine-7-carboxylate, which was deprotected with TFA/DCM (6 ml, 1:1) for 1 h. The mixture was concentrated and the residue was triturated with ethyl ether to provide 1.8 mg of the title compound. 1H-NMR (300 MHz, CDCl3) δ 9.0 (s, 1H), 8.5 (dd, 1H), 8.4 (s, 1H), 7.9 (dd, 1H), 7.4 (m, 2H), 4.9 (m, 1H), 3.0 (m, 2H), 2.6 (m, 4H), 2.3 (m, 2H).

Workup

  1. waitAfter 15 minutes
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. washwashed with 15 mL of water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-d5a860f289c14e50b86528b0e5c22f52
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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