(1S,4S,5S)-2-azabicyclo[2.2.1]heptan-5-ol

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

Procedure: The 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid was combined with (1S,4S,5S)-2-azabicyclo[2.2.1]heptan-5-ol following amide formation method 3 which gave 7-cyclopentyl-2-(5-((1S,4S,5S)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (40 mg, 63% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.84 (br. s., 0.4H, Rotamer) 9.54 (br. s., 0.6H, Rotamer) 8.98-8.82 (m, 1H) 8.80 (s, 0.4H, Rotamer) 8.59 (s, 0.6H, Rotamer) 8.57-8.48 (m, 1H) 7.97 (d, J=7.07 Hz, 0.4H, Rotamer) 7.86 (d, J=6.57 Hz, 0.6H, Rotamer) 6.46 (s, 1H) 4.78 (m, 1H) 4.74 (br. s., 0.4H, Rotamer) 4.46 (br. s., 1H) 4.17 (br. s., 0.6H, Rotamer) 4.07 (d, J=9.09 Hz, 0.4H, Rotamer) 3.91 (d, J=11.62 Hz, 0.6H, Rotamer) 3.64-3.49 (m, 0.6H, Rotamer) 3.49-3.269 (m, 1H+0.4H, Rotamer) 3.15 (s, 6H) 2.73 (m, 0.6H, Rotamer) 2.67 (m, 0.4H, Rotamer) 2.57 (m, 2H) 2.25-1.92 (m, 5H) 1.81-1.42 (m, 5H) HR-MS (m/z MH+) 490.26 RT 4.25 min

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

Procedure: The 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid was combined with (1S,4S,5S)-2-azabicyclo[2.2.1]heptan-5-ol following amide formation method 3 which gave 7-cyclopentyl-2-(5-((1S,4S,5S)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (40 mg, 63% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.84 (br. s., 0.4H, Rotamer) 9.54 (br. s., 0.6H, Rotamer) 8.98-8.82 (m, 1H) 8.80 (s, 0.4H, Rotamer) 8.59 (s, 0.6H, Rotamer) 8.57-8.48 (m, 1H) 7.97 (d, J=7.07 Hz, 0.4H, Rotamer) 7.86 (d, J=6.57 Hz, 0.6H, Rotamer) 6.46 (s, 1H) 4.78 (m, 1H) 4.74 (br. s., 0.4H, Rotamer) 4.46 (br. s., 1H) 4.17 (br. s., 0.6H, Rotamer) 4.07 (d, J=9.09 Hz, 0.4H, Rotamer) 3.91 (d, 1=11.62 Hz, 0.6H, Rotamer) 3.64-3.49 (m, 0.6H, Rotamer) 3.49-3.269 (m, 1H+0.4H, Rotamer) 3.15 (s, 6H) 2.73 (m, 0.6H, Rotamer) 2.67 (m, 0.4H, Rotamer) 2.57 (m, 2H) 2.25-1.92 (m, 5H) 1.81-1.42 (m, 5H) HR-MS (m/z MH+) 490.26 RT 4.25 min

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

Procedure: The 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid was combined with (1S,4S,5S)-2-azabicyclo[2.2.1]heptan-5-ol following amide formation method 3 which gave 7-cyclopentyl-2-(5-((1S,4S,5S)-5-hydroxy-2-azabicyclo[2.2.1]heptane-2-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (40 mg, 63% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.84 (br. s., 0.4H, Rotamer) 9.54 (br. s., 0.6H, Rotamer) 8.98-8.82 (m, 1H) 8.80 (s, 0.4H, Rotamer) 8.59 (s, 0.6H, Rotamer) 8.57-8.48 (m, 1H) 7.97 (d, J=7.07 Hz, 0.4H, Rotamer) 7.86 (d, J=6.57 Hz, 0.6H, Rotamer) 6.46 (s, 1H) 4.78 (m, 1H) 4.74 (br. s., 0.4H, Rotamer) 4.46 (br. s., 1H) 4.17 (br. s., 0.6H, Rotamer) 4.07 (d, J=9.09 Hz, 0.4H, Rotamer) 3.91 (d, J=11.62 Hz, 0.6H, Rotamer) 3.64-3.49 (m, 0.6H, Rotamer) 3.49-3.269 (m, 1H+0.4H, Rotamer) 3.15 (s, 6H) 2.73 (m, 0.6H, Rotamer) 2.67 (m, 0.4H, Rotamer) 2.57 (m, 2H) 2.25-1.92 (m, 5H) 1.81-1.42 (m, 5H) HR-MS (m/z MH+) 490.26 RT 4.25 min