Thiophenol → 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]-N-methylethanamine

HRID 216399Notes

Reaction equation

HRID 216399 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]([CH3:65])([CH2:63][CH3:64])[CH2:9][C:10]1[N:11]=[C:12]([CH2:34][CH:35]([N:49]([CH3:62])S(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)[C:36]2[CH:41]=[CH:40][C:39]([C:42]3[CH:47]=[CH:46][C:45]([F:48])=[CH:44][N:43]=3)=[CH:38][CH:37]=2)[N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=1.C1(S)C=CC=CC=1>CN(C)C=O>[CH3:7][C:8]([CH3:65])([CH2:63][CH3:64])[CH2:9][C:10]1[N:11]=[C:12]([CH2:34][CH:35]([C:36]2[CH:37]=[CH:38][C:39]([C:42]3[CH:47]=[CH:46][C:45]([F:48])=[CH:44][N:43]=3)=[CH:40][CH:41]=2)[NH:49][CH3:62])[N:13]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 68668057N-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-N-methyl-4-nitrobenzenesulfonamide

Product 1

HCID 686674932-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]-N-methylethanamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Potassium carbonate (1.1 g, 7.7 mmol) was added to an ambient temperature solution of N-{2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethyl}-N-methyl-4-nitrobenzenesulfonamide (2.5 g, 3.1 mmol) and benzenethiol (0.64 mL, 6.2 mmol) in N,N-dimethylformamide (20 mL). After stirring at 50° C. for 3 h, then at 70° C. for a further 3 h, the reaction mixture was cooled and partitioned between diethyl ether and saturated aqueous sodium bicarbonate. The organic phase was dried (magnesium sulfate) and concentrated. Chromatography over silica eluting with 0-100% ethyl acetate (containing 5% 2 M ammonia in methanol)/hexane afforded 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]-N-methylethanamine.

Workup

  1. waitat 70° C. for a further 3 h
  2. temperaturethe reaction mixture was cooled
  3. custompartitioned between diethyl ether and saturated aqueous sodium bicarbonate
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-49dd2044648c4a8caee5db89327d3264
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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