Methanol → 2-Amino-4-(4-fluorophenyl)-5-[2-[4-(6-fluorobenzofuran-3-yl)piperidin-1-yl]ethyl]thiazole

HRID 393176Notes

Reaction equation

HRID 393176 reaction equation
Br.[NH2:2][C:3]1[S:4][C:5]([CH2:15][CH2:16]Br)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:7]=1.Cl.[F:19][C:20]1[CH:34]=[CH:33][C:23]2[C:24]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:25][O:26][C:22]=2[CH:21]=1.C(N(C(C)C)CC)(C)C.CO>O>[NH2:2][C:3]1[S:4][C:5]([CH2:15][CH2:16][N:30]2[CH2:31][CH2:32][CH:27]([C:24]3[C:23]4[CH:33]=[CH:34][C:20]([F:19])=[CH:21][C:22]=4[O:26][CH:25]=3)[CH2:28][CH2:29]2)=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[N:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 81531DiisopropylethylamineHCID 226493382-Amino-5-(2-bromoethyl)-4-(4-fluorophenyl)thiazole hydrobromideHCID 226493394-(6-Fluorobenzofuran-3-yl)piperidine hydrochloride

Product 1

HCID 98032362-Amino-4-(4-fluorophenyl)-5-[2-[4-(6-fluorobenzofuran-3-yl)piperidin-1-yl]ethyl]thiazoleYield 64.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.917 g of 2-amino-5-(2-bromoethyl)-4-(4-fluorophenyl)thiazole hydrobromide, 0.511 g of 4-(6-fluorobenzofuran-3-yl)piperidine hydrochloride, 1.5 ml of diisopropylethylamine and 3 ml of methanol was stirred with heating under reflux for 12 hours. The reaction mixture was cooled to room temperature and then poured into water, followed by extraction with chloroform. The extract solution was dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure, after which ether was added to the residue and the crystals were collected by filtration. The crystals were recrystallized from ethanol to obtain 0.57 g of 2-amino-4-(4-fluorophenyl)-5-[2-[4-(6-fluorobenzofuran-3-yl)piperidin-1-yl]ethyl]thiazole.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 12 hours
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe extract solution was dried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionafter which ether was added to the residue
  7. filtrationthe crystals were collected by filtration
  8. customThe crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-093a27cf382844b68d0c2b55813f5c29
Source dataset
uspto-grants-2004_10
Patent number
US06806275B2

Reaction notes

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