Ammonium Chloride → HCID 178424251, compound

HRID 1618051Notes

Reaction equation

HRID 1618051 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[CH:5][C:4]([C:9](=[O:27])[CH2:10][C@H:11]([C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH3:18])=[CH:3]1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:28]1[C:23]([C:22]2[CH:21]=[CH:20][C:19]([C@H:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[CH2:10][C:9]([C:4]3[CH:5]=[CH:6][C:7](=[O:8])[N:2]([CH3:1])[CH:3]=3)=[O:27])=[CH:26][CH:25]=2)=[N:24][N:30]=[N:29]1

Participants

5

Reactant 3

HCID 25517Ammonium Chloride2×HCID 33557Sodium Azide2×HCID 67015760HCID 67015760, compound

Product 1

HCID 178424251HCID 178424251, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)-4-(3-(1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-3-oxo-1-o-tolyl-propyl)benzonitrile (60 mg, 168 μmol) in N,N-dimethylformamide (1 mL) was added sodium azide (54.7 mg, 842 μmol) and ammonium chloride (45.0 mg, 842 μmol). The reaction mixture was heated to 80° C. for 24 h, then another portion of sodium azide (54.7 mg, 842 μmol) and ammonium chloride (45.0 mg, 842 μmol) was added and the reaction mixture was stirred at 80° C. for another 72 h, then concentrated in vacuo. The residue was suspended in dichloro-methane/methanol 19:1, filtered, and the filtrate was purified by chromatography (SiO2, gradient dichloromethane to dichloromethane/methanol 9:1) afforded the product as a salt. This was partitioned between ethyl acetate and 1 M aq. hydrochloric acid solution. After removal of the aqueous layer, the organic layer was dried over magnesium sulfate, filtered, evaporated and precipitated with dichloromethane and heptane to produce the title compound (25 mg, 37%). White solid, MS (ESI+): m/z=: 400.2 [M+H]+.

Workup

  1. concentrationconcentrated in vacuo
  2. filtrationfiltered
  3. customthe filtrate was purified by chromatography (SiO2, gradient dichloromethane to dichloromethane/methanol 9:1)
  4. customafforded the product as a salt
  5. customThis was partitioned between ethyl acetate and 1 M aq. hydrochloric acid solution
  6. customAfter removal of the aqueous layer
  7. dry with materialthe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customprecipitated with dichloromethane and heptane

Sources & evidence

ORD record
ord-5d6f97e82b1e4a24b59f7b73b0f61ad0
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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