Hydrochloric Acid → 5'-chloro-N6-(3-fluorobenzyl)-N2'-(piperidin-4-yl)-2,4'-bipyridine-2',6-diamine

HRID 1623280Notes

Reaction equation

HRID 1623280 reaction equation
[Cl:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)[N:23]=2)=[CH:4][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[N:6][CH:7]=1.Cl.O1CCOCC1>>[Cl:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=3)[N:23]=2)=[CH:4][C:5]([NH:8][CH:9]2[CH2:10][CH2:11][NH:12][CH2:13][CH2:14]2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66936988HCID 66936988, compound

Product 1

HCID 601421355'-chloro-N6-(3-fluorobenzyl)-N2'-(piperidin-4-yl)-2,4'-bipyridine-2',6-diamineYield 141.1%

Procedure

A mixture of tert-butyl 4-(5′-chloro-6-(3-fluorobenzylamino)-2,4′-bipyridin-2′-yl-amino)piperidine-1-carboxylate (220 mg, 0.430 mmol), HCl 4M in Dioxane (7 mL, 28.0 mmol) was stirred at ambient temperature for 1 hr. The solvent was evaporated under reduced pressure to yield a solid which was further dried under high vacuum to yield 250 mg of the title compound as a HCl salt. A portion of the title compound was purified by prep LC, and then lyapholized to yield 19.0 mg of the title compound as a TFA salt. LCMS (m/z): 412.2 (MH+), retention time=0.60 min.; 1H NMR (300 MHz, METHANOL-d4, 25° C.). 6 ppm 1.66-1.83 (m, 2H) 2.25 (dd, J=14.21, 3.08 Hz, 2H) 3.08-3.21 (m, 2H) 3.36-3.51 (m, 2H) 3.96-4.12 (m, 1H) 4.65 (s, 2H) 6.74 (s, 1H) 6.91 (s, 1H) 6.94 (s, 1H) 6.98-7.06 (m, 1H) 7.12 (d, J=9.96 Hz, 1H) 7.19 (d, J=7.62 Hz, 1H) 7.31-7.43 (m, 1H) 7.77-7.85 (m, 1H) 8.09 (s, 1H)

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customto yield a solid which
  3. customwas further dried under high vacuum

Sources & evidence

ORD record
ord-14ec774d399545f49d979a0edf4d4eaf
Source dataset
uspto-grants-2014_07
Patent number
US08778951B2

Reaction notes

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