Potassium Carbonate → HCID 178507751, compound

HRID 1994015Notes

Reaction equation

HRID 1994015 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+].[NH2:35][C:36]1[N:37]=[N:38][C:39](Cl)=[CH:40][CH:41]=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].[F:24][C:2]([F:1])([F:23])[O:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]2[NH:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][C:39]4[N:38]=[N:37][C:36]([NH2:35])=[CH:41][CH:40]=4)=[CH:18][CH:17]=3)=[N:14][N:15]=2)=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 216436-Amino-3-chloropyridazineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 178515916HCID 178515916, compound

Product 1

HCID 178507751HCID 178507751, compoundYield 58.1%

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 (112.0 mg, 0.33 mmol) was dissolved in 2 mL of anhydrous DMF in a 5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (132.8 mg, 0.66 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 15 min, then 3-amino-6-chloropyridazine (47.4 mg, 0.366 mmol) was added, followed by anhydrous K2CO3 (46.0 mg, 0.33 mmol). Then the vial was capped and microwaved at 250° C. for 15 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 (52.1 mg of brown crystalline solid).

Workup

  1. customThen the vial was capped
  2. custommicrowaved at 250° C. for 15 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-b4fbd4335cf345a291379f77d2f8fbbb
Source dataset
uspto-grants-2010_01
Patent number
US07652051B2

Reaction notes

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