[4-(aminomethyl)oxan-4-yl]methanol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the crude product from step 1 (0.944 g, 5.58 mmol) in THF (5 ml) (a dark brown solution) at 0° C. was added LAH (5.58 ml, 5.58 mmol) dropwise via a syringe. The brown mixture was warmed to room temperature and stirred for 18 hours. The resulting mixture was yellow cloudy. LC/MS showed containing desired product. To the reaction was added sodium sulfate decahydrate solid at 0° C. The mixture was stirred at room temperature for 20 min., then filtered and washed with DCM. The yellow filtrate was concentrated in vacuo to give 0.74 g of orange oil. This crude material was used in the next step without further purification.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using 2-(2-(1-tert-butyl-5-(4-fluorophenyl)-1H-pyrazol-4-yl)thiazol-4-yl)acetic acid and [4-(aminomethyl)tetrahydro-2H-pyran-4-yl]methanol and by reaction and purification in the same manner as in the method described in Example 1, step 7, the title compound was obtained. by reaction and purification in the same manner as in the method

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of ethyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (10 g, 54.64 mmol) in THF (50 mL) is added dropwise to a suspension of lithium aluminum hydride (8.26 g, 218.5 mmol) in THF (100 mL) at 0° C. The reaction mixture is warmed to room temperature and stirred for 4 h. The mixture is cooled to 0° C. and ice cold water (30 mL) is added slowly. The mixture is extracted with EtOAc (2×200 mL) and the organic layers are combined, dried (Na2SO4) and concentrated to afford the title crude compound (8 g, >99%) which is used in the next step without purification. The mixture is cooled to 0° C. The mixture is extracted with EtOAc (2×200 mL) dried (Na2SO4) concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To the crude product from step 1 (0.944 g, 5.58 mmol) in THF (5 ml) (a dark brown solution) at 0° C. was added LAH (5.58 ml, 5.58 mmol) dropwise via a syringe. The brown mixture was warmed to room temperature and stirred for 18 hours. The resulting mixture was yellow cloudy. LC/MS showed containing desired product. To the reaction was added sodium sulfate decahydrate solid at 0° C. The mixture was stirred at room temperature for 20 min., then filtered and washed with DCM. The yellow filtrate was concentrated in vacuo to give 0.74 g of orange oil. This crude material was used in the next step without further purification.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 4-thioxo-1,3-thiazolidin-2-one (898 mg) in ethanol (15 mL) was added a solution (5 mL) of [4-(aminomethyl)tetrahydro-2H-pyran-4-yl]methanol (1.00 g) in ethanol, and the mixture was heated under reflux overnight. The reaction mixture was cooled to room temperature, the precipitate was collected by filtration, and the obtained powder was washed with ethyl acetate to give the title compound (1.44 g). the mixture was heated under reflux overnight the precipitate was collected by filtration the obtained powder was washed with ethyl acetate