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Diisopropylethylamine → 2-methylthio-4-(4-fluorophenyl)-5-[2-[4-(5-fluoro-1H-benzotriazol-1-yl)piperidin-1-yl]ethyl]imidazole

HRID 2186796
Notes
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Reaction equation

HRID 2186796 reaction equation
[CH3:1][S:2][C:3]1[NH:4][C:5]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[C:6]([CH2:8][CH2:9]Cl)[N:7]=1.[F:18][C:19]1[CH:33]=[CH:32][C:22]2[N:23]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[N:24]=[N:25][C:21]=2[CH:20]=1.C(N(C(C)C)CC)(C)C>CO>[CH3:1][S:2][C:3]1[NH:7][C:6]([CH2:8][CH2:9][N:29]2[CH2:28][CH2:27][CH:26]([N:23]3[C:22]4[CH:32]=[CH:33][C:19]([F:18])=[CH:20][C:21]=4[N:25]=[N:24]3)[CH2:31][CH2:30]2)=[C:5]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 154620992-Methylthio-5-(2-chloroethyl)-4-(4-fluorophenyl)imidazoleHCID 154627724-(5-fluoro-1H-benzotriazol-1-yl)piperidineHCID 178503441HCID 178503441, compound

Product 1

HCID 120431632-methylthio-4-(4-fluorophenyl)-5-[2-[4-(5-fluoro-1H-benzotriazol-1-yl)piperidin-1-yl]ethyl]imidazole
Yield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.141 g of 2-methylthio-4-(2-chloroethyl)-5-(4-fluorophenyl)imidazole, 2-methylthio-5-(2-chloroethyl)-4-(4-fluorophenyl)imidazole, 0.095 g of 4-(5-fluoro-1H-benzotriazol-1-yl)piperidine, 0.19 ml of diisopropylethylamine and 0.6 ml of methanol was stirred with heating under reflux for 17 hours. After the mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and the residue was purified by a flush chromatography (silica gel: Chromatorex NHDM1020, eluent: hexane-ethyl acetate=1:3). The purified product was recrystallized from ethanol-hexane to obtain 0.104 g of 2-methylthio-4-(4-fluorophenyl)-5-[2-[4-(5-fluoro-1H-benzotriazol-1-yl)piperidin-1-yl]ethyl]imidazole {2-methylthio-5-(4-fluorophenyl)-4-[2-[4-(5-fluoro-1H-benzotriazol-1-yl)piperidin-1-yl]ethyl]imidazole}.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 17 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was purified by a flush chromatography (silica gel: Chromatorex NHDM1020, eluent: hexane-ethyl acetate=1:3)
  5. customThe purified product was recrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-a60259a133e543dabb026052ef2af4cb
Source dataset
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06407121B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes