Hydrochloric Acid → HCID 66959075, compound

HRID 1360598Notes

Reaction equation

HRID 1360598 reaction equation
Cl.[Br:2][C:3]1[C:4]([C:22]#[N:23])=[N:5][N:6]([CH2:20][CH3:21])[C:7]=1[CH2:8][C:9]([NH:12]C(=O)OC(C)(C)C)([CH3:11])[CH3:10]>C(O)C>[NH2:12][C:9]([CH3:10])([CH3:11])[CH2:8][C:7]1[N:6]([CH2:20][CH3:21])[N:5]=[C:4]([C:22]#[N:23])[C:3]=1[Br:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66958753HCID 66958753, compound

Product 1

HCID 66959075HCID 66959075, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Hydrogen chloride (21 mL of a 3.6 M solution in ethanol) was added to a solution of tert-butyl 2-(4-bromo-3-cyano-1-ethyl-1H-pyrazol-5-yl)-1,1-dimethylethylcarbamate (5.6 g, 15 mmol), prepared in Example 1244, in ethanol (75 mL), and the reaction was stirred at room temperature for two days and concentrated under reduced pressure. The residue was suspended in water (50 mL), and aqueous sodium hydroxide (50% w/w) was added to adjust the mixture to pH 12. The basic mixture was extracted with dichloromethane (2×50 mL), and the combined extracts were dried over sodium sulfate, filtered, and concentrated under reduced pressure to provide 4.1 g of 5-(2-amino-2-methylpropyl)-4-bromo-1-ethyl-1H-pyrazole-3-carbonitrile as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionaqueous sodium hydroxide (50% w/w) was added
  3. extractionThe basic mixture was extracted with dichloromethane (2×50 mL)
  4. dry with materialthe combined extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-902f8e91cefd4bccadd736c353317354
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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