Methanol → (S)-2-Butyl-10-(4-methyl-3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene dihydrochloride

HRID 1350467Notes

Reaction equation

HRID 1350467 reaction equation
C([Cl:4])(=O)C.[CH2:5]([C:9]1[S:18][C:17]2[NH:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[N:13]=[C:12]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[C@@H:25]([CH2:30][CH2:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH2:24]3)[C:11]=2[N:10]=1)[CH2:6][CH2:7][CH3:8].CO>C(O)C>[ClH:4].[ClH:4].[CH2:5]([C:9]1[S:18][C:17]2[NH:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[N:13]=[C:12]([N:23]3[CH2:28][CH2:27][N:26]([CH3:29])[C@@H:25]([CH2:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH2:24]3)[C:11]=2[N:10]=1)[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 136005597(S)-2-Butyl-10-(4-methyl-3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene

Product 1

HCID 136360203(S)-2-Butyl-10-(4-methyl-3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene dihydrochlorideYield 82.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add a solution of acetyl chloride (0.15 mL, 2.1 mmol) in absolute ethanol at ambient temperature to (S)-2-Butyl-10-(4-methyl-3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene (0.19 g, 0.41 mmol) in absolute ethanol, with added drops of methanol to solubilize the freebase, and concentrate under reduced pressure gives the title compound (0.18 g). Mass spectrum (APCI+, m/e): 460 (M+1−2HCl); exact mass spectrum (ES+, m/e, C27H33N5S.2HCl): calc. 460.2535 (M+1−2HCl), found 460.2556.

Workup

  1. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-93738a88cf5643f2b01093d19ecd87be
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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