1-Phenethylamine, (-)- → HCID 67062310, compound

HRID 1268735Notes

Reaction equation

HRID 1268735 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH2:20][CH3:21])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15](F)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[C:22]1([C@@H:28]([NH2:30])[CH3:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])O.[Na+]>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([CH2:20][CH3:21])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:30][C@H:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH3:29])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 758181-Phenethylamine, (-)-HCID 516892Sodium BicarbonateHCID 178629784-[4-(3-Chlorophenyl)-2-ethyl-1,3-thiazol-5-yl]-2-fluoropyridine

Product 1

HCID 67062310HCID 67062310, compoundYield 107.6%

Conditions

Temperature
150 °C

Procedure

A mixture of 4-(3-chlorophenyl)-2-ethyl-5-(2-fluoro-4-pyridyl)-1,3-thiazole (0.35 g, 1.1 mmol) and (S)-1-phenylethylamine (1.4 mL, 11 mmol) was stirred at 150° C. for 16 hrs. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The extract was washed with water, dried and concentrated. The obtained oil was treated with 10% hydrogen chloride-methanol to give the title compound (0.27 g, yield 56%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. concentrationconcentrated
  6. additionThe obtained oil was treated with 10% hydrogen chloride-methanol

Sources & evidence

ORD record
ord-495e3c80e77545efa9ccd6d17df3487f
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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