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

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

Reactant 3

HCID 2906Cyclopentylamine

HCID 516892Sodium Bicarbonate

HCID 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%).