Hydrochloric Acid → HCID 18510670, compound

HRID 1370264Notes

Reaction equation

HRID 1370264 reaction equation
Cl.[C:2]([C:4]([O:31][Si](C)(C)C)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([CH:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH2:15]2)=[O:13])=[CH:7][CH:6]=1)#[N:3]>C1COCC1>[C:2]([C:4]([OH:31])([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:5]1[CH:6]=[CH:7][C:8]([NH:11][C:12]([CH:14]2[O:18][N:17]=[C:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)[CH2:15]2)=[O:13])=[CH:9][CH:10]=1)#[N:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18510733HCID 18510733, compound

Product 1

HCID 18510670HCID 18510670, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

) HCl 3N (0.010 mol) was added to a solution of (±)-N-[4-[cyano[(trimethylsilyl)oxy] phenylmethyl]phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide (0.010 mol) in THF (50 ml). The reaction mixture was stirred for 15 minutes at 65° C. The reaction mixture was washed with water and extracted with EtOAc. The separated organic layer was dried (Na2SO4), filtered and the solvent was evaporated, yielding 4.2 g of (±)-N-[4-(cyanohydroxyphenylmethyl)phenyl]-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarboxamide (compound 495).

Workup

  1. washThe reaction mixture was washed with water
  2. extractionextracted with EtOAc
  3. dry with materialThe separated organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9dd581299ae8475db2aaa8567af3459f
Source dataset
uspto-grants-2003_06
Patent number
US06583141B1

Reaction notes

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