Triethylamine → HCID 86656168, compound

HRID 1192480Notes

Reaction equation

HRID 1192480 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH:18](O)[CH3:19])=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[CH:15][CH:14]=[CH:13]2.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:9]1[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)[CH3:19])=[N+:34]=[N-:35]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 67246690HCID 67246690, compound

Product 1

HCID 86656168HCID 86656168, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-[8-(2-fluorophenyl)quinolin-7-yl]ethanol (0.039 g, 0.14 mmol) in methylene chloride (0.9 mL) was added triethylamine (0.0305 mL, 0.22 mmol), followed by methanesulfonyl chloride (0.014 mL, 0.18 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 (0.4 mL) and treated with sodium azide (0.0474 g, 0.73 mmol) at room temperature overnight. After diluting with ethyl acetate, the mixture was washed with water and brine, dried over magnesium sulfate and then evaporated to dryness. The crude product was used in next step (33 mg, 77%). LCMS calculated for C17H14FN4(M+H)+: m/z=293.1; found: 293.1.

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 (0.4 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-83d7ee61c62e4c9bbe5aa034ae463a27
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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