Hydrochloric Acid → HCID 71008298, compound

HRID 1025583Notes

Reaction equation

HRID 1025583 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[N:20](COCC[Si](C)(C)C)[N:19]=[CH:18][C:17]=3[C:29]#[N:30])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl>C(O)C>[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[NH:20][N:19]=[CH:18][C:17]=3[C:29]#[N:30])=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71008061HCID 71008061, compound

Product 1

HCID 71008298HCID 71008298, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(4-(Morpholine-4-carbonyl)phenylamino)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazole-4-carbonitrile (880 mg, 2.06 mmol) was dissolved in 40 mL of ethanol. Hydrochloric acid (2N) was added and the mixture was stirred at room temperature overnight. After 16 hrs at room temperature, LC/MS indicated 60% desired material and 40% un-reacted starting material. The mixture was heated to 65° C. and stirred for 2 hrs. LC/MS indicated complete consumption of the starting material and the formation of the desired product. The mixture was treated with sodium hydroxide solution (4 g NaOH in 40 mL of water) under ice bath. The resulting mixture was extracted with ethyl acetate twice (350 mL). The organic layer was washed with brine and dried over sodium sulfate. TLC indicated a clean spot. Solvents were evaporated and the residue was triturated with dry ether to give 5-[4-(morpholine-4-carbonyl)-phenylamino]-1H-pyrazole-4-carbonitrile as a white solid (530 mg, 86.6% yield). H-NMR is consistent with the desired structure. LC/MS is clean and consistent with the desired molecular weight. LC/MS clacd for C15H15N5O2 (m/e) 297.12, obsd 298.0 (M+H, ES+).

Workup

  1. waitAfter 16 hrs at room temperature
  2. customun-reacted
  3. temperatureThe mixture was heated to 65° C.
  4. stirringstirred for 2 hrs
  5. customconsumption of the starting material
  6. additionThe mixture was treated with sodium hydroxide solution (4 g NaOH in 40 mL of water) under ice bath
  7. extractionThe resulting mixture was extracted with ethyl acetate twice (350 mL)
  8. washThe organic layer was washed with brine
  9. dry with materialdried over sodium sulfate
  10. customSolvents were evaporated
  11. customthe residue was triturated with dry ether

Sources & evidence

ORD record
ord-106ae8e61c7d4ffa9348f165be51c66e
Source dataset
uspto-grants-2014_05
Patent number
US08729078B2

Reaction notes

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