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Diisopropylethylamine → (S)-6-Fluoro-10-[4-methyl-3-(2-methylsulfanyl-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene dihydrochloride

HRID 131483
Notes
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Reaction equation

HRID 131483 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]=[C:14]([NH2:16])[C:13]3[CH:12]=[C:11]([CH3:17])[S:10][C:9]=3[NH:8][C:7]=2[CH:18]=1.[CH3:19][N:20]1[CH2:25][CH2:24]N[CH2:22][C@@H:21]1[CH2:26][CH2:27][S:28][CH3:29].C(N(C(C)C)CC)(C)C>CS(C)=O.C1(C)C=CC=CC=1.C(OCC)(=O)C.[OH-].[Na+]>[ClH:1].[ClH:1].[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]=[C:14]([N:16]3[CH2:24][CH2:25][N:20]([CH3:19])[C@@H:21]([CH2:26][CH2:27][S:28][CH3:29])[CH2:22]3)[C:13]3[CH:12]=[C:11]([CH3:17])[S:10][C:9]=3[NH:8][C:7]=2[CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 81531DiisopropylethylamineHCID 45099614(2S)-1-Methyl-2-[2-(methylsulfanyl)ethyl]piperazineHCID 692119036-Fluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

Product 1

HCID 69210390(S)-6-Fluoro-10-[4-methyl-3-(2-methylsulfanyl-ethyl)-piperazin-1-yl]-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulene dihydrochlorideYield 71.3%

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolvent
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent
HCID 14798Sodium HydroxideSolvent

Procedure

Heat a mixture of 6-fluoro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride salt (0.135 g, 0.476 mmol), (S)-1-methyl-2-(2-methylsulfanyl-ethyl)-piperazine (0.166 g, 0.95 mmol) and diisopropyl ethylamine (0.083 mL, 0.476 mmol) in DMSO (0.2 mL) and toluene (0.8 mL) at 110° C. for 46 hours. Dilute the reaction mixture with ethyl acetate and 0.1N sodium hydroxide solution. The ethyl acetate extract gives 0.196 g. of the crude product. Silica gel chromatography, eluting with methylene chloride:methanol (100:5), gives 0.081 g of the title compound as an orange oil. The dihydrochloride salt precipitates in ethyl acetate as an orange solid: mp 194° C.; mass spectrum (ion spray): m/z=405 (M+1).

Workup

  1. temperatureHeat
  2. extractionThe ethyl acetate extract
  3. customgives 0.196 g
  4. washSilica gel chromatography, eluting with methylene chloride:methanol (100:5)

Sources & evidence

ORD record
ord-e21af35d42574f028d2c71b60c1652a0
Source dataset
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07384934B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes