Ammonium Chloride → HCID 178428856, compound

HRID 384498Notes

Reaction equation

HRID 384498 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][NH:4][C:3]=1[CH2:9][O:10][C:11]1[CH:12]=[C:13]([CH:16]=[C:17]([O:19][CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:18]=1)[C:14]#[N:15].[N-:27]=[N+:28]=[N-:29].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][C:2]1[C:7](=[O:8])[C:6]2[C:5](=[CH:1][CH:2]=[CH:3][CH:9]=2)[NH:4][C:3]=1[CH2:9][O:10][C:11]1[CH:12]=[C:13]([C:14]2[NH:29][N:28]=[N:27][N:15]=2)[CH:16]=[C:17]([O:19][CH2:20][CH:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[CH:18]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 685083823-[(1,4-Dihydro-3-methyl-4-oxo-2-pyridinyl)methoxy]-5-[(tetrahydro-2H-pyran-4-yl)methoxy]benzonitrile

Product 1

HCID 178428856HCID 178428856, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-[(3-methyl-4-oxo-1,4-dihydropyridin-2-yl)methoxy]-5-(tetrahydro-2H-pyran-4-ylmethoxy)benzonitrile (100 mg) in DMF (2 mL) were added sodium azide (18 mg) and ammonium chloride (15 mg), followed by stirring at 100° C. for 24 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in a 1M aqueous sodium hydroxide solution and washed with diethyl ether. The aqueous layer was adjusted to a pH of 2 by adding 1M hydrochloric acid, followed by extraction with chloroform and a mixed solvent of chloroform-methanol (5:1). The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by thin layer chromatography (developer: chloroform/methanol=6/1) and washed with ethyl acetate to obtain 3-methyl-2-{[3-(tetrahydro-2H-pyran-4-ylmethoxy)-5-(1H-tetrazol-5-yl)phenoxy]methyl}quinolin-4(1H)-one (37 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in a 1M aqueous sodium hydroxide solution
  3. washwashed with diethyl ether
  4. additionby adding 1M hydrochloric acid
  5. extractionfollowed by extraction with chloroform
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by thin layer chromatography (developer: chloroform/methanol=6/1)
  10. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-4cfb4f836b0c4993b823b6a1cfaa8241
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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