Cyclopentylamine → N-cyclopentyl-4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amine

HRID 1268734Notes

Reaction equation

HRID 1268734 reaction equation
[CH2:1]([C:3]1[S:4][C:5]([C:15]2[CH:20]=[CH:19][N:18]=[C:17](F)[CH:16]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=2)[N:7]=1)[CH3:2].[CH:22]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)([O-])O.[Na+]>>[CH:22]1([NH:27][C:17]2[CH:16]=[C:15]([C:5]3[S:4][C:3]([CH2:1][CH3:2])=[N:7][C:6]=3[C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[CH:9]=3)[CH:20]=[CH:19][N:18]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 2906CyclopentylamineHCID 516892Sodium BicarbonateHCID 99008852-Ethyl-5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazole

Product 1

HCID 9947156N-cyclopentyl-4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5-yl]pyridin-2-amineYield 33%

Procedure

A mixture of 2-ethyl-5-(2-fluoro-4-pyridyl)-4-(3-methylphenyl)-1,3-thiazole (0.48 g, 1.6 mmol) and cyclopentylamine (1.6 mL, 16 mmol) was heated under reflux for 14 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 crude crystals were recrystallized from ethyl acetate to give the title compound (0.19 g, yield 33%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 14 hrs
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe obtained crude crystals
  8. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-76c8ee316d99435e8a2ee29413824db2
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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