Methanesulfonamide → HCID 10024718, compound

HRID 2056251Notes

Reaction equation

HRID 2056251 reaction equation
[CH2:1]([C:3]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([OH:24])=O)[CH:17]=1)[CH3:2].[CH3:25][S:26]([NH2:29])(=[O:28])=[O:27]>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH2:1]([C:3]1[N:11]=[C:10]([C:12]([F:14])([F:15])[F:13])[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([NH:29][S:26]([CH3:25])(=[O:28])=[O:27])=[O:24])[CH:17]=1)[CH3:2]

Participants

5

Reactant 2

HCID 72879MethanesulfonamideHCID 10404737HCID 10404737, compound

Product 1

HCID 10024718HCID 10024718, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 6-ethyl-9-(3-carboxyphenyl)-2-trifluoromethylpurine (450 mg, 1.24 mmol), methylsulfonamide (238 mg, 2.48 mmol), N-ethyl-N′-3-dimethylaminopropylcarbodimide (238 mg, 1.24 mmol), 4-dimethylaminopyridine (151 mg, 1.24 mmol) and N,N -dimethylformamide (3 ml) were stirred at 50-60° C. for 12 hours. The solvent was concentrated under vacuum, and the residue was dissolved in 30 ml of ethyl acetate, washed with sodium bicarbonate (1×30 mL), brine (1×30 mL), dried (MgSO4), and concentrated. The residue was purified by chromatography over silica gel using a gradient elution from 10% to 20% MeOH/DCM to give 305 mg (56% yield) of 6-ethyl-9-(3-methylsulfonylaminocarbonylphenyl)-2-trifluromethylpurine. 1H NMR (300 MHz, CDCl3) δ 9.43 (b, 1H), 8.59 (s, 1H), 8.30 (s, 1H), 8.18 (d, J=7.5 Hz, 1H), 7.98 (d, J=7.5 Hz, 1H), 7.78 (t, J=7.5 Hz, 1H), 3.48 (s, 3H), 3.35 (q, J=7.2 Hz, 2H), 1.52 (t, J=7.5 Hz, 3H). [ESMS m/z (414.1 (M+H)+)]

Workup

  1. concentrationThe solvent was concentrated under vacuum
  2. dissolutionthe residue was dissolved in 30 ml of ethyl acetate
  3. washwashed with sodium bicarbonate (1×30 mL), brine (1×30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography over silica gel using
  7. washa gradient elution from 10% to 20% MeOH/DCM

Sources & evidence

ORD record
ord-1dd2ea1012ac49eab2098053c1ecbad5
Source dataset
uspto-grants-2008_02
Patent number
US07335654B2

Reaction notes

Loading…