Sodium hydride → HCID 23521721, compound

HRID 392421Notes

Reaction equation

HRID 392421 reaction equation
OC1C=CC([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[CH2:14][NH:15][S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=CC=1.[H-].[Na+].[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Br>CS(C)=O.C(OCC)(=O)C>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][O:24][C:25]1[CH:26]=[CH:27][C:30]([N:15]([CH2:14][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:8]=2)[S:16]([CH2:19][CH3:20])(=[O:17])=[O:18])=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 40672073-Methoxybenzyl bromideHCID 136404401HCID 136404401, compound

Product 1

HCID 23521721HCID 23521721, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-(4-(4-hydroxyphenyl)-N-(ethanesulfonyl) pyrid-3-ylmethylamine (1.0 equiv.) in DMSO (0.15 M) was cooled to 0° C. Sodium hydride (1.1 equiv.; 60% dispersion in oil) was added; after 20 minutes at 0° C. 3-methoxybenzyl bromide (Aldrich; 1.3 equiv.) was added and the reaction warmed to ambient temperature. After stirring overnight the reaction was diluted with ethyl acetate and washed with 0.1 M potassium carbonate, and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via preparative HPLC eluting with 90:10 to 70:30 DCM/ethyl acetate to give the title compound. Anal Calcd for C22H24N2O4S.0.1H2O: C, 64.06; H, 5.86; N, 6.79. Found: C, 63.78; H, 5.89; N, 6.76. MS found 413.0 [M+H]+.

Workup

  1. washwashed with 0.1 M potassium carbonate, and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified via preparative HPLC
  6. washeluting with 90:10 to 70:30 DCM/ethyl acetate

Sources & evidence

ORD record
ord-2d1ab615373548769ca1e48874cdf124
Source dataset
uspto-grants-2004_10
Patent number
US06800651B2

Reaction notes

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