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Diisopropylethylamine → (S)-9-Fluoro-5-[3-phenethyl-piperazine-1-yl]-11H-12-thia-6,11-diaza-dibenzo[a,f]azulene

HRID 1350486
Notes
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Reaction equation

HRID 1350486 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]=[C:14]([NH2:16])[C:13]3[C:12]4[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=4[S:10][C:9]=3[NH:8][C:7]=2[CH:21]=1.[CH2:22]([C@H:30]1[CH2:35]N[CH2:33][CH2:32][NH:31]1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(C(C)C)CC)(C)C>CS(C)=O.C1(C)C=CC=CC=1.C(Cl)Cl>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]=[C:14]([N:16]3[CH2:33][CH2:32][NH:31][C@@H:30]([CH2:22][CH2:23][C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH2:35]3)[C:13]3[C:12]4[CH:17]=[CH:18][CH:19]=[CH:20][C:11]=4[S:10][C:9]=3[NH:8][C:7]=2[CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 1842238412-Amino-8-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine hydrochlorideHCID 44828673(S)-2-Phenethylpiperazine

Product 1

HCID 24887774(S)-9-Fluoro-5-[3-phenethyl-piperazine-1-yl]-11H-12-thia-6,11-diaza-dibenzo[a,f]azuleneYield 33.3%

Reagents, catalysts & solvents 3

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 1140TolueneSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
115 °C

Procedure

Combine 9-fluoro-11H-12-thia-6,11-diaza-dibenzo[a,f]azulen-5-ylamine hydrogen chloride (287 mg, 0.9 mmol), (S)-2-phenethyl-piperazine (340 mg, 1.80 mmol) and diisopropylethyl amine (116 mg, 0.9 mmol) in DMSO (0.5 mL) and toluene (2.0 mL), stir and microwave (300 W, 125 ° C.) for 8 h, then heat to 115 ° C. for 22 h. Cool the reaction to RT, dilute with CH2Cl2, wash with H2O and brine. Dry the organic layer with by Na2SO4. The crude material purify by chromatography on silica gel, gradient (100% CH2Cl2 to 100% CH2Cl2:2N NH3/MeOH=25:1), give 137 mg of title compound.

Workup

  1. temperatureCool
  2. customthe reaction to RT
  3. washwash with H2O and brine
  4. dry with materialDry the organic layer with by Na2SO4
  5. customThe crude material purify by chromatography on silica gel, gradient (100% CH2Cl2 to 100% CH2Cl2:2N NH3/MeOH=25:1)

Sources & evidence

ORD record
ord-8d1e6ef4da8247849abf56d6c85f1e8f
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07214673B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes