Triethylamine → HCID 86656166, compound

HRID 1192476Notes

Reaction equation

HRID 1192476 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([CH:19](O)[CH3:20])=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)[CH:5]=[C:6]([F:8])[CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:34]=[N+:35]=[N-:36].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[N:34]([CH:19]([C:10]1[C:9]([C:4]2[CH:3]=[C:2]([F:1])[CH:7]=[C:6]([F:8])[CH:5]=2)=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[N:17]2)=[CH:12][CH:11]=1)[CH3:20])=[N+:35]=[N-:36]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 67246913HCID 67246913, compound

Product 1

HCID 86656166HCID 86656166, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[8-(3,5-difluorophenyl)quinolin-7-yl]ethanol (0.048 g, 0.17 mmol) in methylene chloride (1 mL) was added triethylamine (0.0352 mL, 0.252 mmol), followed by methanesulfonyl chloride (0.0163 mL, 0.210 mmol). After stirred at room temperature for 30 minutes, the resultant mixture was diluted with dichloromethane, washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure. The crude mesylate was dissolved in N,N-dimethylformamide (0.5 mL) and treated with sodium azide (0.0547 g, 0.841 mmol) at room temperature overnight. After diluted with ethyl acetate, the mixture was washed with water and brine, dried over magnesium sulfate, and evaporated to dryness. The crude product was used in next step (40 mg, 76%). LCMS calculated for C17H13F2N4(M+H)+: m/z=311.1; found: 311.0.

Workup

  1. washwashed with saturated sodium bicarbonate and 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 (0.5 mL)
  5. washthe mixture was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-d998bfd7d04147ae934250489bb356f9
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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