2-Propanesulfonyl chloride → HCID 90403334, compound

HRID 2200653Notes

Reaction equation

HRID 2200653 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[C:9]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:32])[F:31])[CH:24]=3)=[N:8][C:7]=2[N:6]([CH3:34])[C:5]1=[O:35].[CH3:36][CH:37]([S:39](Cl)(=[O:41])=[O:40])[CH3:38]>C(Cl)Cl.O>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][N:10]2[C:11]3[C:12](=[O:13])[N:4]([CH2:3][CH2:2][NH:1][S:39]([CH:37]([CH3:38])[CH3:36])(=[O:41])=[O:40])[C:5](=[O:35])[N:6]([CH3:34])[C:7]=3[N:8]=[C:9]2[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([O:29][C:30]([F:33])([F:31])[F:32])[CH:24]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 824082-Propanesulfonyl chlorideHCID 90402790HCID 90402790, compound

Product 1

HCID 90403334HCID 90403334, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 1-(2-aminoethyl)-7-(4-chlorobenzyl)-3-methyl-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (100 mg, 0.197 mmol) and TEA (40 mg, 0.393 mmol) in DCM (10 mL) was added propane-2-sulfonyl chloride (42 mg, 0.295 mmol) dropwise at 0° C. The resulting mixture was stirred at 40° C. for 16 h. The mixture was diluted with DCM and water, and the phases were separated. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product. This crude material was recrystallized from ethanol to give N-(2-(7-(4-chlorobenzyl)-3-methyl-2,6-dioxo-8-(3-(trifluoromethoxy)phenoxy)-2,3,6,7-tetrahydro-1H-purin-1-yl)ethyl)propane-2-sulfonamide (20 mg, 16.5% yield) as white solid. 1H-NMR (DMSO-d6) δ 7.63-7.59(t, 1H), 7.48(s, 1H), 7.45-7.41(m, 5H), 7.35-7.33(d, 1H), 7.26-7.18(m, 1H), 5.45(s, 2H), 4.01-3.97(t, 1H), 3.29(s, 6H). LCMS retention time 3.195 min; LCMS MH+ 616.

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product
  7. customThis crude material was recrystallized from ethanol

Sources & evidence

ORD record
ord-95caa73b2a62408cb1fda1bec2c2d399
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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