Acetonitrile → HCID 59333361, compound

HRID 1893450Notes

Reaction equation

HRID 1893450 reaction equation
[NH:1]1[CH2:6][CH:5]=[C:4]([C:7]2[N:11]3[C:12]4[C:17]([N:18]=[C:19]([NH:20][CH2:21][CH2:22][CH2:23][OH:24])[C:10]3=[N:9][CH:8]=2)=[CH:16][C:15]([C:25]([F:28])([F:27])[F:26])=[CH:14][CH:13]=4)[CH2:3][CH2:2]1.[S:29](Cl)([CH3:32])(=[O:31])=[O:30].C(#N)C>ClCCl>[CH3:32][S:29]([N:1]1[CH2:2][CH:3]=[C:4]([C:7]2[N:11]3[C:12]4[C:17]([N:18]=[C:19]([NH:20][CH2:21][CH2:22][CH2:23][OH:24])[C:10]3=[N:9][CH:8]=2)=[CH:16][C:15]([C:25]([F:26])([F:28])[F:27])=[CH:14][CH:13]=4)[CH2:5][CH2:6]1)(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 31297Methanesulfonyl chlorideHCID 59333345HCID 59333345, compound

Product 1

HCID 59333361HCID 59333361, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[1-(1,2,3,6-tetrahydro-pyridin-4-yl)-7-trifluoromethyl-imidazo[1,2-a]quinoxalin-4-ylamino]-propan-1-ol as prepared in example 27 (50.0 mg; 0.132 mmol; 1 eq) in anhydrous dichloromethane (660 μL) are successively added N,N′-dimethylaminopyridine (16.1 mg; 0.132 mmol; 1 eq) and mesyl chloride (10.3 μL; 0.132 mmol; 1 eq). The solution is allowed to stir at room temperature for 17 hours after which period the reaction is almost complete. The reaction mixture is concentrated under vacuum and the resulting residue is taken-up with ethyl acetate (10 mL). The organic solution is washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated in vacuum. Two successive column chromatography on silica gel (eluent column 1: ethyl acetate/methanol/triethylamine 8:2:0.2; eluent column 2: dichloromethane/methanol 95:5) and one column chromatography on reversed-phase (C18, acetonitrile) affords the title compound as a white solid (9 mg; 0.020 mmol; 15%)

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. washThe organic solution is washed with brine (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-bb24b76c39fc4031a32c7a43ec7550cd
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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