Potassium Carbonate → HCID 68047229, compound

HRID 2283650Notes

Reaction equation

HRID 2283650 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[CH:5][C:6]([OH:25])=[C:7]([C:9]2[N:13]([CH:14]3[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]3)[N:12]=[CH:11][CH:10]=2)[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:34][C:35]1[C:36](F)=[CH:37][C:38]([F:61])=[C:39]([S:41]([N:44]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([O:57][CH3:58])=[CH:53][C:52]=2[O:59][CH3:60])[C:45]2[S:46][CH:47]=[N:48][N:49]=2)(=[O:43])=[O:42])[CH:40]=1.C(OC)(C)(C)C>CS(C)=O.O>[F:27][C:2]([F:1])([F:26])[C:3]1[CH:4]=[CH:5][C:6]([O:25][C:36]2[CH:37]=[C:38]([F:61])[C:39]([S:41]([N:44]([CH2:50][C:51]3[CH:56]=[CH:55][C:54]([O:57][CH3:58])=[CH:53][C:52]=3[O:59][CH3:60])[C:45]3[S:46][CH:47]=[N:48][N:49]=3)(=[O:42])=[O:43])=[CH:40][C:35]=2[Cl:34])=[C:7]([C:9]2[N:13]([CH:14]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:17]3)[N:12]=[CH:11][CH:10]=2)[CH:8]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 15413tert-Butyl methyl etherHCID 580422535-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-(1,3,4-thiadiazol-2-yl)benzenesulfonamideHCID 136063628tert-Butyl 3-[5-(5-trifluoromethyl-2-hydroxyphenyl)-1H-pyrazol-1-yl]azetidine-1-carboxylate

Product 1

HCID 68047229HCID 68047229, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

tert-Butyl 3-[5-(5-trifluoromethyl-2-hydroxyphenyl)-1H-pyrazol-1-yl]azetidine-1-carboxylate (Preparation 34, 400 mg, 1.04 mmol) and potassium carbonate (450 mg, 3.26 mmol) were combined in dimethylsulfoxide (5 mL). To this slurry was added 5-chloro-N-(2,4-dimethoxybenzyl)-2,4-difluoro-N-1,3,4-thiadiazol-2-ylbenzenesulfonamide (Preparation 6, 482 mg, 1.04 mmol) and stirred at ambient temperature for 3 hours. tert-Butylmethyl ether (30 mL) and water (30 mL) were added and the layers separated. The organic layer was washed with water (2×30 mL), then dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo to give a foam. The foam was purified by silica gel flash column chromatography (20% to 40% ethyl acetate in heptane gradient elution) to afford the title compound as a colourless foam (600 mg, 70%).

Workup

  1. customthe layers separated
  2. washThe organic layer was washed with water (2×30 mL)
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a foam
  7. customThe foam was purified by silica gel flash column chromatography (20% to 40% ethyl acetate in heptane gradient elution)

Sources & evidence

ORD record
ord-d349ca77cf33425d8f03c925c3f5106e
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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