Ammonium Chloride → HCID 68182781, compound

HRID 524441Notes

Reaction equation

HRID 524441 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:31])[CH:11]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH:28]3[CH2:30][CH2:29]3)(=[O:27])=[O:26])=[CH:21][CH:20]=2)[O:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:7][CH:8]=1)#[N:2].[N-:32]=[N+:33]=[N-:34].[Na+].[Cl-].[NH4+]>CN(C=O)C.O>[CH:28]1([S:25]([C:22]2[CH:23]=[CH:24][C:19]([CH:11]([O:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)[C:10]([NH:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]4[N:32]=[N:33][NH:34][N:2]=4)=[CH:8][N:7]=3)=[O:31])=[CH:20][CH:21]=2)(=[O:27])=[O:26])[CH2:30][CH2:29]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68182439HCID 68182439, compound

Product 1

HCID 68182781HCID 68182781, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

The mixture of N-(5-cyano-2-pyridyl)-2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetamide (0.1 g, 0.22 mmol), sodium azide (0.03 g, 0.453 mmol) and ammonium chloride (0.024 g, 0.453 mmol) in DMF (8 mL) was heated at 110° C. for 16 h. After completion, reaction mixture was diluted with water (40 mL) and extracted with ethyl acetate (2×50 mL), combined organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. Crude compound was purified by LCMS purification to afford title compound. (0.020 g).

Workup

  1. customAfter completion, reaction mixture
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washwas washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customCrude compound was purified by LCMS purification

Sources & evidence

ORD record
ord-f6a1fce9a9b84a9faff56e10cdc4a580
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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