Acetyl chloride → HCID 59333356, compound

HRID 1893449Notes

Reaction equation

HRID 1893449 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.[C:29](Cl)(=[O:31])[CH3:30]>ClCCl>[OH:24][CH2:23][CH2:22][CH2:21][NH:20][C:19]1[C:10]2[N:11]([C:7]([C:4]3[CH2:3][CH2:2][N:1]([C:29](=[O:31])[CH3:30])[CH2:6][CH:5]=3)=[CH:8][N:9]=2)[C:12]2[C:17]([N:18]=1)=[CH:16][C:15]([C:25]([F:26])([F:28])[F:27])=[CH:14][CH:13]=2

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 59333345HCID 59333345, compound

Product 1

HCID 59333356HCID 59333356, compoundYield 36%

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 prepared in the previous example (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 acetyl chloride (9.4 μL; 0.132 mmol; 1 eq). The solution is allowed to stir for 17 hours at room temperature until completion of the reaction. The reaction mixture is concentrated under vacuum and the resulting residue is taken-up in ethyl acetate (10 mL). The resulting organic solution is washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated in vacuum. The resulting residue is passed through a silica gel column (dichloromethane/methanol 95:5) to afford the title compound as an off-white solid (20 mg; 0.048 mmol; 36%)

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum
  2. washThe resulting 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-bc7fc177f4a94829a6c504e7d7b069fc
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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