Hydrochloric Acid → HCID 19815937, compound

HRID 2247880Notes

Reaction equation

HRID 2247880 reaction equation
[CH:1]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([CH3:20])[C:9]=2[C:21](=[O:31])[NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:5][CH:4]=1)=O.Cl.[NH2:33]O.C(OC(=O)C)(=O)C.Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.N1C=CC=CC=1.C(OCC)(=O)C.O>[C:1]([C:3]1[O:7][C:6]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([CH3:20])[C:9]=2[C:21](=[O:31])[NH:22][CH2:23][CH2:24][N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)=[CH:5][CH:4]=1)#[N:33]

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 19815891HCID 19815891, compound

Product 1

HCID 19815937HCID 19815937, compoundYield 55.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(5-formyl-2-furyl)-2-methyl-3-(2-morpholinoethylcarbamoyl)-6-phenylpyridine (1.2 g) and hydroxylamine hydrochloride (0.26 g) in a mixture of N,N-dimethylformamide (5 ml) and pyridine (4 ml) was stirred at ambient temperature for 2.5 hours. To the reaction mixture was added acetic anhydride (5 ml) and the resulting solution was stirred at 80° C. for 1 hour. The mixture was poured into a mixture of water and ethyl acetate and adjusted to pH 1.0 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 8.0 with 20% aqueous potassium carbonate and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromotography on silica gel. The column was eluted with a mixture of ethyl acetate and tetrahydrofuran (85:15 V/V) and the fraction was evaporated in vacuo. The residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether to give 4 -(5-cyano-2-furyl)-2-methyl-3-(2-morpholinoethylcarbamoyl)-6-phenylpyridine (0.66 g).

Workup

  1. stirringthe resulting solution was stirred at 80° C. for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. washThe column was eluted with a mixture of ethyl acetate and tetrahydrofuran (85:15 V/V)
  7. customthe fraction was evaporated in vacuo
  8. customThe residue was recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-cfaf476e4734463997d8187f39c5d24b
Source dataset
uspto-grants-1991_08
Patent number
US05037824

Reaction notes

Loading…