Methanesulfonyl chloride → HCID 18767760, compound

HRID 2105649Notes

Reaction equation

HRID 2105649 reaction equation
[NH2:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH3:22])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][CH3:26])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>N1C=CC=CC=1.CCOC(C)=O>[O:23]=[C:14]1[N:13]([CH2:24][CH2:25][CH3:26])[C:12]2[N:11]=[C:10]([C:5]34[CH2:8][CH2:9][C:2]([NH:1][S:28]([CH3:27])(=[O:30])=[O:29])([CH2:7][CH2:6]3)[CH2:3][CH2:4]4)[NH:18][C:17]=2[C:16](=[O:19])[N:15]1[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chloride2×HCID 18767683HCID 18767683, compound

Product 1

HCID 18767760HCID 18767760, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 100 mg of 8-(4-Amino-bicyclo[2.2.2]oct 1-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione. (Example 20), (0.28 mmol) in 2 ml of pyridine chilled in an ice/water bath was added 22 μL of methanesulfonyl chloride (0.28° mmol), 30% completion after 24 h at 10° C. Two more aliquots (22 μL and 50 μL) of methanesulfonyl chloride were added to drive the reaction to completion. The reaction mixture was concentrated in vacuo to afford a yellow oil which was taken up in EtOAc (10 ml) and washed twice with sat'd NaHCO3 (5 ml), once with 0.5N HCl and once with brine. The organic layer was dried over NaSO4 and conc'd to an oil. Crystallized from acetonitrile to afford 27 mg (22%) as a white solid (MH+=438.08). The following compounds were prepared in an analogous manner:

Workup

  1. customthe reaction to completion
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto afford a yellow oil which
  4. washwashed twice with sat'd NaHCO3 (5 ml), once with 0.5N HCl and once with brine
  5. dry with materialThe organic layer was dried over NaSO4 and conc'd to an oil
  6. customCrystallized from acetonitrile
  7. customto afford 27 mg (22%) as a white solid (MH+=438.08)
  8. customThe following compounds were prepared in an analogous manner

Sources & evidence

ORD record
ord-9e9a7ee135b84e108b2bf25f23ab4a2a
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

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