Potassium Carbonate → HCID 178485504, compound

HRID 1994025Notes

Reaction equation

HRID 1994025 reaction equation
[F:1][C:2]([F:24])([F:23])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)=[N:13][N:14]=2)=[CH:6][CH:5]=1.[CH3:25][Si]([N-][Si](C)(C)C)(C)C.[K+].Cl[C:36]1[CH:41]=[CH:40][N:39]=[C:38]([C:42]([NH2:44])=[O:43])[CH:37]=1.[C:45]([O-])([O-:47])=[O:46].[K+].[K+]>CN(C=O)C.CO>[F:24][C:2]([F:1])([F:23])[C:45]([OH:47])=[O:46].[CH3:25][NH:44][C:42]([C:38]1[CH:37]=[C:36]([O:22][C:19]2[CH:20]=[CH:21][C:16]([NH:15][C:12]3[NH:11][C: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:14][N:13]=3)=[CH:17][CH:18]=2)[CH:41]=[CH:40][N:39]=1)=[O:43]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 3035434-Chloropyridine-2-carboxamideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 178516246HCID 178516246, compound

Product 1

HCID 178485504HCID 178485504, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-[5-(4-trifluoromethoxy-phenyl)-4H[1,2,4]triazol-3-ylamino]-phenol (134.5 mg, 0.4 mmol) was dissolved in 2 mL of anhydrous DMF in a 5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (120.0 mg, 0.6 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 15 min, then 4-chloro-2-pyridine-carboxamide (68.2 mg, 0.4 mmol) was added, followed by anhydrous K2CO3 (62.0 mg, 0.44 mmol). Then the vial was capped and microwaved at 150° C. for 30 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 (31.7 mg of white solid).

Workup

  1. customThen the vial was capped
  2. custommicrowaved at 150° C. for 30 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-ae812f5f957b411c8db6f4cf128b3d98
Source dataset
uspto-grants-2010_01
Patent number
US07652051B2

Reaction notes

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