Potassium Carbonate → HCID 59436536, compound

HRID 1402005Notes

Reaction equation

HRID 1402005 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([S:10]([N:13]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=2[O:28][CH3:29])[C:14]2[S:18][N:17]=[CH:16][N:15]=2)(=[O:12])=[O:11])[CH:6]=[CH:7][C:8]=1F)#[N:2].[C:30]([N:34]1[C:38]([NH:39][C:40](=[O:45])[C:41]([F:44])([F:43])[F:42])=[C:37]([C:46]2[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=2[OH:53])[CH:36]=[N:35]1)([CH3:33])([CH3:32])[CH3:31].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[C:30]([N:34]1[C:38]([NH:39][C:40](=[O:45])[C:41]([F:44])([F:43])[F:42])=[C:37]([C:46]2[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=2[O:53][C:8]2[CH:7]=[CH:6][C:5]([S:10]([N:13]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:21]=3[O:28][CH3:29])[C:14]3[S:18][N:17]=[CH:16][N:15]=3)(=[O:11])=[O:12])=[CH:4][C:3]=2[C:1]#[N:2])[CH:36]=[N:35]1)([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 580422543-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamideHCID 59436577N-(1-(tert-butyl)-4-(5-chloro-2-hydroxyphenyl)-1H-pyrazol-5-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 59436536HCID 59436536, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-cyano-N-(2,4-dimethoxybenzyl)-4-fluoro-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 68, 150 mg, 0.35 mmol) in dimethyl sulfoxide (10 ml) was added N-[1-tert-butyl-4-(5-chloro-2-hydroxyphenyl)-1H-pyrazol-5-yl]-2,2,2-trifluoroacetamide (Preparation 209, 131 mg, 0.36 mmol) and potassium carbonate (135 mg, 0.86 mmol) and the flask was purged with nitrogen (×3). The resulting suspension was stirred at room temperature for 18 hours before pouring into sodium hydroxide (1 M aqueous solution) and extracting with dichloromethane. The combined organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to afford a pale yellow oil. This was purified by column chromatography (80 g silica gel column) eluting with ethyl acetate:heptane (1:1, by volume) to furnish the title compound as a pale yellow oil, 157 mg, 59% yield.

Workup

  1. customthe flask was purged with nitrogen (×3)
  2. additionbefore pouring into sodium hydroxide (1 M aqueous solution)
  3. extractionextracting with dichloromethane
  4. dry with materialThe combined organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto afford a pale yellow oil
  8. customThis was purified by column chromatography (80 g silica gel column)
  9. washeluting with ethyl acetate:heptane (1:1, by volume)

Sources & evidence

ORD record
ord-1b67ca9b8cc341f693c8e178555095fc
Source dataset
uspto-grants-2014_12
Patent number
US08907101B2

Reaction notes

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