Potassium Carbonate → HCID 178485503, compound

HRID 387454Notes

Reaction equation

HRID 387454 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[NH:10][C:11]([C:14]3[CH:15]=[C:16]([OH:20])[CH:17]=[CH:18][CH:19]=3)=[N:12][N:13]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].[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-:48])([O-])=[O:46].[K+].[K+]>CN(C=O)C.CO>[F:22][C:21]([F:24])([F:23])[C:45]([OH:48])=[O:46].[CH3:25][NH:44][C:42]([C:38]1[CH:37]=[C:36]([O:20][C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:11]3[NH:10][C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:21]([F:22])([F:23])[F:24])[CH:4]=4)=[N:13][N:12]=3)[CH:15]=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 1785159893-[5-(4-Chloro-3-trifluoromethyl-phenylamino)-4h[1,2,4]triazol-3-yl]-phenol

Product 1

HCID 178485503HCID 178485503, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-[5-(4-chloro-3-trifluoromethyl-phenylamino)-4H[1,2,4]triazol-3-yl]-phenol (100 mg, 0.282 mmol) was dissolved in 2 mL of anhydrous DMF in a 5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (140.6 mg, 0.705 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 15 min, then 4-chloro-2-pyridine-carboxamide (52.9 mg, 0.31 mmol) was added, followed by anhydrous K2CO3 (19.5 mg, 0.141 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 (25.0 rug of 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-2fe858e6e05a4c8ea20eaf2972da8b63
Source dataset
uspto-grants-2013_02
Patent number
US08372971B2

Reaction notes

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