Triethylamine → HCID 58368505, compound

HRID 1192703Notes

Reaction equation

HRID 1192703 reaction equation
[Cl:1][C:2]1[C:7]2=[CH:8][O:9][N:10]=[C:6]2[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)=[C:4]([CH:18](O)[CH3:19])[CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:33]=[N+:34]=[N-:35].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:33]([CH:18]([C:4]1[CH:3]=[C:2]([Cl:1])[C:7]2=[CH:8][O:9][N:10]=[C:6]2[C:5]=1[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=1)[CH3:19])=[N+:34]=[N-:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 58368677HCID 58368677, compound

Product 1

HCID 58368505HCID 58368505, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[4-chloro-7-(3-fluorophenyl)-2,1-benzisoxazol-6-yl]ethanol (0.094 g, 0.32 mmol) in methylene chloride (2 mL) was added triethylamine (0.067 mL, 0.48 mmol), followed by methanesulfonyl chloride (0.031 mL, 0.40 mmol). After stirring at room temperature for 30 minutes, the resulting mixture was diluted with dichloromethane, washed with sat. sodium bicarbonate, brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The resulting 1-[4-chloro-7-(3-fluorophenyl)-2,1-benzisoxazol-6-yl]ethyl methanesulfonate was used directly in the next step. LCMS calculated for C16H14ClFNO4S (M+H)+: m/z=370.0; Found: 370.1. The crude mesylate was dissolved in N,N-dimethylformamide (1 mL) and treated with sodium azide (0.105 g, 1.61 mmol) at room temperature overnight. After diluted with ethyl acetate, the mixture was washed with water, brine and then dried over magnesium sulfate and evaporated to dryness. The crude product was used in the next step (90 mg, 88%). LCMS calculated for C15H11ClFN4O (M+H)+: m/z=317.1; Found: 317.0.

Workup

  1. washwashed with sat. sodium bicarbonate, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. dissolutionThe crude mesylate was dissolved in N,N-dimethylformamide (1 mL)
  5. washthe mixture was washed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-3e276d979fee46dbb56e948deb8bccd0
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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