Reaction SMILES: ClC1C(C2C=CC=C(NCC3C=CC=C(F)C=3)N=2)=CC(N[C@@H]2CC[C@H](O)C2)=NC=1.C(N(C(C)C)CC)(C)C.S(Cl)(C)(=O)=O.[N-]=[N+]=[N-].[Na+].[N:48]([C@@H:51]1[CH2:55][CH2:54][C@@H:53]([NH:56][C:57]2[CH:62]=[C:61]([C:63]3[CH:68]=[CH:67][CH:66]=[C:65]([NH:69][CH2:70][C:71]4[CH:76]=[CH:75][CH:74]=[C:73]([F:77])[CH:72]=4)[N:64]=3)[C:60]([Cl:78])=[CH:59][N:58]=2)[CH2:52]1)=[N+]=[N-]>CO.[Pd].C(Cl)Cl>[NH2:48][C@@H:51]1[CH2:55][CH2:54][C@@H:53]([NH:56][C:57]2[CH:62]=[C:61]([C:63]3[CH:68]=[CH:67][CH:66]=[C:65]([NH:69][CH2:70][C:71]4[CH:76]=[CH:75][CH:74]=[C:73]([F:77])[CH:72]=4)[N:64]=3)[C:60]([Cl:78])=[CH:59][N:58]=2)[CH2:52]1
Reactant: [N-]=[N+]=N[C@@H]1CC[C@@H](Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)C1
Agent: [Pd]
Agent: CS(=O)(=O)Cl
Agent: O[C@H]1CC[C@@H](Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)C1
Solvent: ClCCl
Solvent: CO
Solvent: CCN(C(C)C)C(C)C
Product: N[C@@H]1CC[C@@H](Nc2cc(-c3cccc(NCc4cccc(F)c4)n3)c(Cl)cn2)C1
Temperature: 25 °C
Reaction time: 0.5 h

Procedure:
To (1S,3R)-3-(5′-chloro-6-(3-fluorobenzylamino)-2,4′-bipyridin-2′-yl-amino)cyclopentanol (28 mg, 0.068 mmol) was added DCM (1 ml), diisopropyl ethylamine (0.030 ml, 0.170 mmol) then mesyl chloride (5.81 μl, 0.075 mmol), stirred at ambient temperature for 1 hr, and followed by LCMS. Another 3 uL of mesyl chloride was added and the reaction mixture was stirred an additional 30 minutes at ambient temperature. DCM was removed by rotary evaporation, and crude (1S,3R)-3-(5′-chloro-6-(3-fluorobenzylamino)-2,4′-bipyridin-2′-yl-amino)cyclopentyl LCMS (m/z): 491.2 (MH+), retention time=0.76 min. was redissolved in 2 mL DMF. Sodium azide (8.82 mg, 0.136 mmol) and diisopropyl ethylamine (0.030 ml, 0.170 mmol) were added, and the reaction mixture was heated at 50° C. for 18 hours, at which point only N2′-((1R,3R)-3-azidocyclopentyl)-5′-chloro-N6-(3-fluorobenzyl)-2,4′-bipyridine-2′,6-diamine was observed by LCMS (m/z): 438.2 (MH+), retention time=0.83 min. The resulting reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was removed, and the organic layer was washed with water (1×) then saturated salt solution (1×), dried over sodium sulfate, and reduced to constant mass. Crude N2′-((1R,3R)-3-azidocyclopentyl)-5′-chloro-N6-(3-fluorobenzyl)-2,4′-bipyridine-2′,6-diamine (20 mg, 0.046 mmol, LCMS (m/z): 438.2 (MH+), retention time=0.83 min.) was dissolved in 1 mL of methanol, and 10% palladium on charcoal (4.86 mg, 0.046 mmol) was added under argon. H2 was bubbled through the solution while stirring for 1 hr at ambient temperature, and the reaction was followed by LCMS. The crude reaction mixture was filtered over celite washed with methanol, reduced, redissolved in DMSO, filtered and purified through prep LC. The resulting product fractions were combined, then 50 mL of 1 M NaOH and 50 mL of EtOAC were added. The aqueous layer was removed, the organic layer was washed with saturated salt solution, dried over sodium sulfate, and reduced to constant mass. 8 mg of the desired compound was obtained. LCMS (m/z): 412.1 (MH+), retention time=0.58 min.; 1H NMR (300 MHz, CHLOROFORM-d, 25° C.) δ ppm 1.31-1.54 (m, 2H) 1.71-1.86 (m, 4H) 1.98-2.13 (m, 1H) 2.20-2.35 (m, 1H) 3.54 (qd, J=6.35, 6.15 Hz, 1H) 4.14 (sxt, J=6.56 Hz, 1H) 4.55-4.67 (m, 3H) 5.11 (t, J=5.86 Hz, 1H) 6.40 (d, J=8.50 Hz, 1H) 6.56 (s, 1H) 6.88-7.02 (m, 1H) 7.12-7.16 (m, 1H) 7.29-7.34 (m, 1H) 7.47-7.52 (m, 1H) 8.09 (s, 1H).