Water → HCID 58941286, compound

HRID 747617Notes

Reaction equation

HRID 747617 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:22][C:23]2[NH:27][N:26]=[N:25][N:24]=2)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([CH2:28][C:29]2[C:34]([F:35])=[CH:33][CH:32]=[CH:31][C:30]=2[F:36])[CH:3]=1.IC.[C:39](=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:22][C:23]2[N:27]([CH3:39])[N:26]=[N:25][N:24]=2)[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([CH2:28][C:29]2[C:30]([F:36])=[CH:31][CH:32]=[CH:33][C:34]=2[F:35])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178492889HCID 178492889, compound

Product 1

HCID 58941286HCID 58941286, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2.7 g of N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-3,4-dimethoxy-N-[(1H-tetrazol-5-yl)methyl]benzenesulfonamide dissolved in 50 ml of DMF are added, at room temperature, 1.07 g of iodomethane and 1.04 g of potassium carbonate. After 48 hours at room temperature, the medium is poured into water and then extracted with ethyl acetate. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 90/10 (v/v) toluene/ethyl acetate mixture to give 1 g of N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-3,4-dimethoxy-N-[(1-methyl-1H-tetrazol-5-yl)methyl]benzenesulfonamide (compound 152) 1H NMR δ in ppm (DMSO d6): 3.81 (s, 3H); 3.90 (s, 3H); 3.93 (q, 1H); 4.05 (m, 4H); 4.93 (d, 1H); 5.42 (d, 1H); 6.58 (s, 1H); 7.00 (d, 1H); 7.10-7.46 (unresolved complex, 7H). m.p.=180.8° C. and 0.71 g of N-[4-chloro-2-(2,6-difluorobenzyl)phenyl]-3,4-dimethoxy-N-[(2-methyl-2H-tetrazol-5-yl)methyl]benzenesulfonamide (compound 151) 1H NMR δ in ppm (DMSO d6): 3.81 (s, 3H); 3.89 (s, 3H); 4.13 (s, 2H); 4.26 (s, 3H); 4.77 (d, 1H); 5.25 (d, 1H); 6.57 (s, 1H); 6.86 (d, 1H); 7.11-7.47 (unresolved complex, 7H). m.p.=136.3° C.

Workup

  1. additionare added, at room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with a 90/10 (v/v) toluene/ethyl acetate mixture

Sources & evidence

ORD record
ord-bb8becb1c0a14bae9c57cad851e179ab
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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