Potassium Carbonate → HCID 178506387, compound

HRID 387443Notes

Reaction equation

HRID 387443 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[NH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)=[N:14][N:15]=2)=[CH:6][CH:5]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Cl.Cl[C:37]1[CH:42]=[CH:41][N:40]=[CH:39][CH:38]=1.[C:43]([O-])([O-:45])=[O:44].[K+].[K+]>CN(C=O)C.CO>[F:24][C:2]([F:1])([F:23])[C:43]([OH:45])=[O:44].[N:40]1[CH:41]=[CH:42][C:37]([O:22][C:19]2[CH:20]=[CH:21][C:16]([C:13]3[NH:12][C:11]([NH:10][C:7]4[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:23])[F:24])=[CH:9][CH:8]=4)=[N:15][N:14]=3)=[CH:17][CH:18]=2)=[CH:38][CH:39]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 818524-Chloropyridine hydrochlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 178515916HCID 178515916, compound

Product 1

HCID 178506387HCID 178506387, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-[5-(4-trifluoromethoxy-phenylamino)-4H[1,2,4]triazol-3-yl]-phenol (106.0 mg, 0.315 mmol) was dissolved in 2 mL of anhydrous DMF in a 5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (157.2 mg, 0.788 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 15 min, then 4-chloropyridine hydrochloride (56.7 mg, 0.378 mmol) was added, followed by anhydrous K2CO3 (44.0 mg, 0.315 mmol). Then the vial was capped and microwaved at 250° C. for 20 min. Then the reaction mixture was diluted with ca. 1 mL of MeOH, filtered through 0.22 um syringe filter and purified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA. The product was isolated as a TFA salt (66.5 mg of off-white solid).

Workup

  1. customThen the vial was capped
  2. custommicrowaved at 250° C. for 20 min
  3. filtrationfiltered through 0.22 um syringe
  4. filtrationfilter
  5. custompurified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA

Sources & evidence

ORD record
ord-6f97be2f9206476b9441324287d58a1a
Source dataset
uspto-grants-2013_02
Patent number
US08372971B2

Reaction notes

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