1-Propanamine, 3,3,3-trifluoro-, hydrochloride (1:1)

General procedure: To a stirred solution of dihydroxylated tetrahydronaphthalene (2 mmol) NaIO4 (1.5 equiv) was added in THF/H2O (25 mL/2 mL). After stirring for 30 min at 20 C under Ar atmosphere, H2O was added (40 mL). The mixture was then extracted with CH2Cl2 (3 × 20 mL) and the combined organic layers were dried over Na2SO4. The resulting solution containing the dialdehyde derivative concentrated to half of its volume was used without purification for the next reaction. To the solution of the dialdehyde was added fluorine-containing amine hydrochloride (1 equiv) and NaHCO3 (2 equiv) or benzylamine or methylbenzylamine (1 equiv, without NaHCO3). Then the mixture was stirred at 20 C for 10 min and, after adding NaBH3CN (1 equiv) and AcOH (2 drops), stirring was continued for another 3 h at 20 C. The reaction mixture was diluted with H2O (20 mL) and extracted with CH2Cl2 (3 × 20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/EtOAc or nhexane/acetone). Characterization and 1 H NMR and 13C NMR spectra of the synthetized compounds are available in the Supporting Information.General procedure: To a stirred solution of dihydroxylated tetrahydronaphthalene (2 mmol) NaIO4 (1.5 equiv) was added in THF/H2O (25 mL/2 mL). After stirring for 30 min at 20 C under Ar atmosphere, H2O was added (40 mL). The mixture was then extracted with CH2Cl2 (3 × 20 mL) and the combined organic layers were dried over Na2SO4. The resulting solution containing the dialdehyde derivative concentrated to half of its volume was used without purification for the next reaction. To the solution of the dialdehyde was added fluorine-containing amine hydrochloride (1 equiv) and NaHCO3 (2 equiv) or benzylamine or methylbenzylamine (1 equiv, without NaHCO3). Then the mixture was stirred at 20 C for 10 min and, after adding NaBH3CN (1 equiv) and AcOH (2 drops), stirring was continued for another 3 h at 20 C. The reaction mixture was diluted with H2O (20 mL) and extracted with CH2Cl2 (3 × 20 mL). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane/EtOAc or nhexane/acetone). Characterization and 1 H NMR and 13C NMR spectra of the synthetized compounds are available in the Supporting Information.To a stirred mixture of 3-bromo-6-methanesulfonyl-1H-pyrazolo[3, 4-d]pyrimidine (2.30 g, 8.30 mmol) and TEA (12.6 g, 125 mmol) in DMA (20.0 mL) was added 3, 3, 3- trifluoropropan-1-amine hydrochloride (6.21 g, 41.5 mmol) at room temperature under nitrogen atmosphere. After stirring for additional 16 h, the resulting mixture was diluted with water (50.0 mL). The precipitated solid was collected by filtration and washed with water (2 x 10.0 mL) to give 3-bromo-N-(3, 3, 3-trifluoropropyl)-1H-pyrazolo[3, 4-d]pyrimidin-6-amine (2.0 g, 78%) as light yellow solid. 1H NMR (400 MHz, DMSO-d6) d 13.31 (s, 1H), 8.70 (s, 1H), 7.86 (s, 1H), 3.55 (s, 2H), 2.58 (td, J = 11.1, 5.0 Hz, 2H). LC/MS (ESI, m/z): [(M + 1)]+ = 310.00, 312.00To a solution of trans-4-[5-bromo-2-chloro-7H-pyrrolo[2, 3-d]pyrimidin-7- yl]cyclohexan-1-ol (5.0 g, 15.1 mmol) in NMP (25.0 mL) were added DIEA (11.7 g, 90.7 mmol) and Pd2dba3 (356 mg, 0.39 mmol), Xantphos (375 mg, 0.65 mmol) and K3PO4 (4.40 g, 20.7 mmol) were added to a solution of 2-chloro-4-iodopyridine [153034-86-7] (1.55 g, 6.47 mmol) in anhydrous DMF (25 mL) in a sealed tube while N2 was bubbling. After 10 min,

Molecular Weight:149.54
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:149.0219114
Monoisotopic Mass:149.0219114
Topological Polar Surface Area:26
Heavy Atom Count:8
Complexity:48.6
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes