Hydrochloric Acid → (S)-6,7-Difluoro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene dihydrochloride

HRID 131453Notes

Reaction equation

HRID 131453 reaction equation
[F:1][C:2]1[C:3]([F:27])=[CH:4][C:5]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][NH:18][C@@H:17]([CH2:21][CH2:22][O:23][CH3:24])[CH2:16]3)[C:12]3[CH:11]=[C:10]([CH3:25])[S:9][C:8]=3[NH:7][C:6]=2[CH:26]=1.[ClH:28]>C(OCC)(=O)C.C(O)C>[ClH:28].[ClH:28].[F:1][C:2]1[C:3]([F:27])=[CH:4][C:5]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][NH:18][C@@H:17]([CH2:21][CH2:22][O:23][CH3:24])[CH2:16]3)[C:12]3[CH:11]=[C:10]([CH3:25])[S:9][C:8]=3[NH:7][C:6]=2[CH:26]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 135434034(S)-6,7-Difluoro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene

Product 1

HCID 136355246(S)-6,7-Difluoro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene dihydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve (S)-6,7-difluoro-10-[3-(2-methoxy-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene (730 mg, 1.86 mmol) in ethyl acetate. Add 2.5 equivalents of hydrogen chloride in ethanol. After 3 hours filter the precipitate, wash with ethyl acetate and dry under vacuum to give the title compound (856 mg, 99%): Mass Spectrum (ESMS) 393 (M+1); 391 (M−1), mp 198-202° C. (dec).

Workup

  1. filtrationAfter 3 hours filter the precipitate
  2. washwash with ethyl acetate
  3. customdry under vacuum

Sources & evidence

ORD record
ord-7034f21f99704b53aa20cfe9a9a44522
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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