Triethylamine → HCID 58368611, compound

HRID 1192573Notes

Reaction equation

HRID 1192573 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[N:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:11]([C:18]#[N:19])=[CH:10][C:9]=2[CH:20]([OH:22])[CH3:21])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)Cl>[CH3:30][S:31]([O:22][CH:20]([C:9]1[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[N:16]2)=[C:11]([C:18]#[N:19])[CH:10]=1)[CH3:21])(=[O:33])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58368566HCID 58368566, compound

Product 1

HCID 58368611HCID 58368611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 8-(3-fluorophenyl)-7-(1-hydroxyethyl)quinoline-5-carbonitrile (20 mg, 0.07 mmol) in methylene chloride (1 mL) was added triethylamine (0.28 mL, 2.0 mmol) followed by methanesulfonyl chloride (0.12 mL, 1.5 mmol). The reaction was stirred at room temperature for 30 minutes, quenched with water and then extracted with dichloromethane. The combined organic layers were washed with brine and dried over magnesium sulfate and concentrated to dryness under reduced pressure. The residue was used directly in the next step (28 mg, 100%). LCMS calculated for C19H16FN2O3S (M+H)+: m/z=371.1; Found: 371.1.

Workup

  1. customquenched with water
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-12996c5022854fd1a70199efaf1597f0
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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