Diisopropylethylamine → HCID 178517497, compound

HRID 393178Notes

Reaction equation

HRID 393178 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-7273cbb9e1454ddf804fcf858f66f4b4
Source dataset
uspto-grants-2004_10
Patent number
US06806275B2

Reaction notes

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