Potassium Carbonate → HCID 178507750, compound

HRID 661394Notes

Reaction equation

HRID 661394 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:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)=[N:12][N:13]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].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-:46])([O-])=[O:44].[K+].[K+]>CN(C=O)C.CO>[F:22][C:21]([F:24])([F:23])[C:43]([OH:46])=[O:44].[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]=[CH:16][C:17]([O:20][C:39]4[N:38]=[N:37][C:36]([NH2:35])=[CH:41][CH:40]=4)=[CH:18][CH:19]=3)=[N:12][N:13]=2)=[CH:4][C:3]=1[C:21]([F:22])([F:23])[F:24]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 216436-Amino-3-chloropyridazineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 178515915HCID 178515915, compound

Product 1

HCID 178507750HCID 178507750, compoundYield 19.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-[5-(4-chloro-3-trifluoromethyl-phenylamino)-4H [1,2,4]triazol-3-yl]-phenol (120.0 mg, 0.338 mmol) was dissolved in 3 mL of anhydrous DMF in a 5 mL microwave vial (Personal Chemistry). Solid potassium bis(trimethylsilyl)amide (81.0 mg, 0.406 mmol) was added and the reaction mixture was stirred with heating at 80° C. for 15 min, then 3-amino-6-chloro-pyridazine (48.2 mg, 0.372 mmol) was added, followed by anhydrous K2CO3 (46.7 mg, 0.338 mmol). Then the vial was capped and microwaved at 200° C. for 30 min. After reaction was complete, 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 (18.2 mg).

Workup

  1. customThen the vial was capped
  2. custommicrowaved at 200° C. for 30 min
  3. customAfter reaction
  4. filtrationfiltered through 0.22 um syringe
  5. filtrationfilter
  6. custompurified by reverse-phase preparative HPLC in acetonitrile/water system with 0.01% TFA

Sources & evidence

ORD record
ord-2e515eb2a17b4471bc71c4d26310c2e1
Source dataset
uspto-grants-2011_12
Patent number
US08084618B2

Reaction notes

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