Hydrochloric Acid → HCID 178505486, compound

HRID 561210Notes

Reaction equation

HRID 561210 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]#[N:17])[O:13][N:12]=2)[CH2:7][CH2:6]1.Cl.[NH+]1C=CC=CC=1.[N-:30]=[N+:31]=[N-:32].[Na+].Cl>CN1C(=O)CCC1.O>[Br:1][C:2]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:15]=[C:14]([C:16]3[NH:32][N:31]=[N:30][N:17]=3)[O:13][N:12]=2)[CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 21584435Pyridinium hydrochlorideHCID 533885303-[4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl]isoxazole-5-carbonitrile

Product 1

HCID 178505486HCID 178505486, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 3-[4-(2-bromo-5-fluorophenoxy)piperidin-1-yl]isoxazole-5-carbonitrile (1.4 g, 3.82 mmol), pyridinium hydrochloride (0.9 g, 7.79 mmol) and sodium azide (1.3 g, 20.00 mmol) in NMP (12 mL) was stirred and heated at 130° C. bath for 2 h. After cooling, the mixture was diluted with water and acidified with 1N HCl (some precipitate appeared). The whole mixture was then extracted with EtOAc. The EtOAc extract was washed with water (3×), dried (Na2SO4) and concentrated. The residue was triturated with diethyl ether to give the title compound as a light brown powder.

Workup

  1. temperatureAfter cooling
  2. extractionThe whole mixture was then extracted with EtOAc
  3. extractionThe EtOAc extract
  4. washwas washed with water (3×)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-7bbc3825a6b04ff7bbd2aa8177bc8d01
Source dataset
uspto-grants-2011_11
Patent number
US08063224B2

Reaction notes

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