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

HRID 1350465Notes

Reaction equation

HRID 1350465 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][NH:26][C@@H:25]([CH2:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=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][NH:26][C@@H:25]([CH2:29][CH2:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH2:24]3)[C:11]=2[N:10]=1)[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 136005542(S)-2-Butyl-10-(3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene

Product 1

HCID 136360202(S)-2-Butyl-10-(3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene dihydrochlorideYield 88.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Add a solution of acetyl chloride (0.0601 mL, 0.842 mmol) in absolute ethanol at ambient temperature to (S)-2-Butyl-10-(3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene (0.075 g, 0.17 mmol) in absolute ethanol, with added drops of methanol to solubilize the freebase, stir and concentrate under reduced pressure to give the title compound (0.078 g): Mass spectrum (ES+, m/e): 446 (M+1−2HCl); exact mass spectrum (ES+, m/e, C26H31N5S.2HCl): calc. 446.2378 (M+1–2HCl), found 446.2397.

Workup

  1. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-a5543a3a04994d74bb57e4eb0d00a984
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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