Tetrahydrofuran → N-[(4-cyano-3-fluoro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methylene]-2-methylpropanesulfinamide

HRID 2227387Notes

Reaction equation

HRID 2227387 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([C:10]([C:12]2[N:13]([CH3:17])[CH:14]=[N:15][CH:16]=2)=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C[C:19]([S@:22]([NH2:24])=[O:23])(C)C.[CH2:25]1[CH2:29]OC[CH2:26]1>[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([C:10]([C:12]2[N:13]([CH3:17])[CH:14]=[N:15][CH:16]=2)=[N:24][S:22]([CH2:19][CH:25]([CH3:26])[CH3:29])=[O:23])=[CH:9][C:2]=1[F:1])#[N:5]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 185332052-Fluoro-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile

Product 1

HCID 86584782N-[(4-cyano-3-fluoro-phenyl)-(3-methyl-3H-imidazol-4-yl)-methylene]-2-methylpropanesulfinamide

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
75 °C

Procedure

2-Fluoro-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile (2.56 g, 11.2 mmol), titanium(IV) ethoxide (7.02 mL, 33.5 mmol) and commercially available (R)-(+)-2-methyl-2-propanesulfinamide (1.35 g, 11.17 mmol) were dissolved in anhydrous THF (100 mL) and heated at 75° C. for 7 days. The solution was cooled, diluted with brine (100 mL), filtered through a celite pad and washed generously with EtOAc and H2O. The filtrate was separated, dried (MgSO4), and purified using SiO2 chromatography (0-3% MeOH/CH2Cl2) to give the title compound.

Workup

  1. temperatureThe solution was cooled
  2. filtrationfiltered through a celite pad
  3. washwashed generously with EtOAc and H2O
  4. customThe filtrate was separated
  5. dry with materialdried (MgSO4)
  6. custompurified

Sources & evidence

ORD record
ord-d7add2c54afe42fc81cc80de95f0db98
Source dataset
uspto-grants-2002_07
Patent number
US06413964B1

Reaction notes

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