Acetyl chloride → (S)-5-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-8-trifluoromethyl-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene dihydrochloride

HRID 131514Notes

Reaction equation

HRID 131514 reaction equation
C([Cl:4])(=O)C.[CH3:5][O:6][CH2:7][CH2:8][C@@H:9]1[NH:14][CH2:13][CH2:12][N:11]([C:15]2[C:24]3[C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[S:21][C:20]=3[NH:19][C:18]3[CH:29]=[CH:30][C:31]([C:33]([F:36])([F:35])[F:34])=[CH:32][C:17]=3[N:16]=2)[CH2:10]1>C(O)C>[ClH:4].[ClH:4].[CH3:5][O:6][CH2:7][CH2:8][C@@H:9]1[NH:14][CH2:13][CH2:12][N:11]([C:15]2[C:24]3[C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[S:21][C:20]=3[NH:19][C:18]3[CH:29]=[CH:30][C:31]([C:33]([F:35])([F:36])[F:34])=[CH:32][C:17]=3[N:16]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 135507279(S)-5-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-8-trifluoromethyl-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene

Product 1

HCID 136384239(S)-5-[3-(2-Methoxy-ethyl)-piperazin-1-yl]-8-trifluoromethyl-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene dihydrochlorideYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add a solution of acetyl chloride (0.078 mL, 1.1 mmol) in absolute ethanol to a solution of (S)-5-[3-(2-methoxy-ethyl)-piperazin-1-yl]-8-trifluoromethyl-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene (0.10 g, 0.22 mmol) in absolute ethanol and isolate the precipitated solid by suction filtration. Dry the solid under reduced pressure to give the title compound (0.095 g). Exact mass spectrum (ES+, m/e, C23H23F3N4OS.2HCl): calc. 461.1623 (M+1-2HCl), found 461.1613.

Workup

  1. customisolate the precipitated solid
  2. filtrationby suction filtration
  3. customDry the solid under reduced pressure

Sources & evidence

ORD record
ord-f80e3e0bd27c49328f09c610d84c1f62
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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