Sodium Azide → HCID 58368556, compound

HRID 1192574Notes

Reaction equation

HRID 1192574 reaction equation
CS(O[CH:6]([C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=2)=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[N:15]2)=[C:10]([C:25]#[N:26])[CH:9]=1)[CH3:7])(=O)=O.[N-:27]=[N+:28]=[N-:29].[Na+]>CN(C)C=O>[N:27]([CH:6]([C:8]1[CH:9]=[C:10]([C:25]#[N:26])[C:11]2[CH:12]=[CH:13][CH:14]=[N:15][C:16]=2[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[CH:19]=1)[CH3:7])=[N+:28]=[N-:29]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58368611HCID 58368611, compound

Product 1

HCID 58368556HCID 58368556, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-[5-cyano-8-(3-fluorophenyl)quinolin-7-yl]ethyl methanesulfonate (28 mg, 0.076 mmol) and sodium azide (24 mg, 0.38 mmol) in N,N-dimethylformamide (0.5 mL) was stirred at room temperature overnight. The mixture was then quenched with water, extracted with ethyl acetate. The combined organic layers were washed with water and brine, and then dried over magnesium sulfate and evaporated to dryness. The residue was used directly in the next step (20 mg, 83%). LCMS calculated for C18H13FN5 (M+H)+: m/z =318.1; Found: 318.1.

Workup

  1. customThe mixture was then quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5abb6d12844f4b60bd3114fc4fb8cd41
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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