Hydrochloric Acid → HCID 136138781, compound

HRID 2365429Notes

Reaction equation

HRID 2365429 reaction equation
[Cl:1]C1C=C(C=CC=1)C(O)=O.[C:11]1([C:17]2[CH:21]=[N:20][NH:19][C:18]=2[C:22]2[C:30]3[C:25](=[N+:26]([O-])[CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.COS(OC)(=O)=O.[CH2:39]([NH2:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[ClH:47]>C(#N)C.CCOC(C)=O.CO>[ClH:1].[ClH:47].[CH2:39]([NH:46][C:27]1[N:26]=[C:25]2[NH:24][CH:23]=[C:22]([C:18]3[NH:19][N:20]=[CH:21][C:17]=3[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:30]2=[CH:29][CH:28]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 7504Benzylamine2×HCID 178524355HCID 178524355, compound

Product 1

HCID 136138781HCID 136138781, compoundYield 2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 3-(4-phenyl-2H-pyrazol-3-yl)-1H-pyrrolo[2,3-b]pyridine 7-oxide meta-chlorobenzoate salt (247 mg, 0.57 mmol) in acetonitrile (3 mL) was added dimethylsulfate (124 mg, 0.98 mmol) and the mixture heated to 60° C. for 16 hours. After this time the reaction was cooled to room temperature and benzylamine (490 mg, 4.57 mmol) added. The reaction was then reheated to 55° C. and held at this temperature for 7 hours. Additional benzylamine (245 mg, 2.28 mmol) was then added and heating continued for an additional 17 hours. The mixture was then cooled to room temperature and diluted with EtOAc (50 mL). The organic was then washed with 10% sodium bicarbonate solution (50 mL) and dried over sodium sulfate. Filtration, concentration and purification of the residue by preparative thin layer chromatography afforded an oil. This material was treated with 1.25M Hydrogen Chloride in methanol (5 mL) and the solution concentrated. Trituration of the residue with diethyl ether and isolation of the resulting solids gave the title compound as a light yellow solid in 2% yield.

Workup

  1. temperatureAfter this time the reaction was cooled to room temperature
  2. customwas then reheated to 55° C.
  3. temperatureheating
  4. waitcontinued for an additional 17 hours
  5. temperatureThe mixture was then cooled to room temperature
  6. washThe organic was then washed with 10% sodium bicarbonate solution (50 mL)
  7. dry with materialdried over sodium sulfate
  8. filtrationFiltration, concentration and purification of the residue by preparative thin layer chromatography
  9. customafforded an oil
  10. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-2ac3541f6f324c1f9fc60053980a5105
Source dataset
uspto-grants-2014_04
Patent number
US08697697B2

Reaction notes

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