Diisopropylethylamine → HCID 178517497, compound

HRID 2186795Notes

Reaction equation

HRID 2186795 reaction equation
Cl[CH2:2][CH2:3][C:4]1[S:8][C:7]([OH:9])=[N:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1.Cl.[F:18][C:19]1[CH:33]=[CH:32][C:22]2[C:23]([CH:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:24][O:25][C:21]=2[CH:20]=1.C(N(C(C)C)CC)(C)C>CO>[OH:9][C:7]1[S:8][C:4]([CH2:3][CH2:2][N:29]2[CH2:30][CH2:31][CH:26]([C:23]3[C:22]4[CH:32]=[CH:33][C:19]([F:18])=[CH:20][C:21]=4[O:25][CH:24]=3)[CH2:27][CH2:28]2)=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:6]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 226493394-(6-Fluorobenzofuran-3-yl)piperidine hydrochlorideHCID 178517496HCID 178517496, compound

Product 1

HCID 178517497HCID 178517497, compoundYield 34.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.134 g of 5-(2-chloroethyl)-2-hydroxy-4-(4-fluorophenyl)thiazole, 0.11 g of 4-(6-fluorobenzofuran-3-yl)piperidine hydrochloride, 0.28 ml of diisopropylethylamine and 0.5 ml of methanol was stirred with heating under reflux for 15 hours. After the reaction 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: Merckkieselgel 60 230- to 400-mesh, eluent: hexane-ethyl acetate=2:1). The purified product was recrystallized from ethyl acetate-hexane to obtain 0.066 g of 2-hydroxy-4-(4-fluorophenyl)-5-[2-[4-(6-fluorobenzofuran-3-yl)piperidin-1-yl]ethyl]thiazole.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 15 hours
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was purified by a flush chromatography (silica gel: Merckkieselgel 60 230- to 400-mesh, eluent: hexane-ethyl acetate=2:1)
  5. customThe purified product was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-ebefa5c696a142f880ec838e55b4c120
Source dataset
uspto-grants-2002_06
Patent number
US06407121B1

Reaction notes

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