Acetyl chloride → (S)-10-[3-(2-Methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-Isopropyl-4H-3-thia-4,9-diaza-benzo[f]azulene dihydrochloride

HRID 131467Notes

Reaction equation

HRID 131467 reaction equation
C([Cl:4])(=O)C.[CH3:5][O:6][CH2:7][CH2:8][C@@H:9]1[N:14]([CH3:15])[CH2:13][CH2:12][N:11]([C:16]2[C:25]3[CH:24]=[C:23]([CH:26]([CH3:28])[CH3:27])[S:22][C:21]=3[NH:20][C:19]3[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=3[N:17]=2)[CH2:10]1>C(O)C>[ClH:4].[ClH:4].[CH3:5][O:6][CH2:7][CH2:8][C@@H:9]1[N:14]([CH3:15])[CH2:13][CH2:12][N:11]([C:16]2[C:25]3[CH:24]=[C:23]([CH:26]([CH3:28])[CH3:27])[S:22][C:21]=3[NH:20][C:19]3[CH:29]=[CH:30][CH:31]=[CH:32][C:18]=3[N:17]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 136090373(S)-10-[3-(2-Methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-isopropyl-4H-3-thia-4,9-diaza-benzo[f]azulene

Product 1

HCID 136384294(S)-10-[3-(2-Methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-Isopropyl-4H-3-thia-4,9-diaza-benzo[f]azulene dihydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add a solution of acetyl chloride (0.13 mL, 1.76 mmol) in absolute ethanol to a solution of (S)-10-[3-(2-methoxy-ethyl)-4-methyl-piperazin-1-yl]-2-isopropyl-4H-3-thia-4,9-diaza-benzo[f]azulene (0.14 g, 0.35 mmol) in absolute ethanol and stir. Concentrate under reduced pressure to give the title compound (0.16 g, 94%): mass spectrum (APCI, m/e): 399 (M+1); exact mass spectrum (ES+, m/e, C22H30N4OS.2HCl): calc. 399.2218 (M+1-2HCl), found 399.2226.

Workup

  1. concentrationConcentrate under reduced pressure

Sources & evidence

ORD record
ord-d14c5fc882e24930b62ec226f3d0964e
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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