Hydrochloric Acid → 5-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-6'-(piperidin-4-yloxy)-3,3'-bipyridin-6-amine

HRID 1406320Notes

Reaction equation

HRID 1406320 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([O:14][CH:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[CH:12][CH:13]=2)=[CH:4][C:3]=1[O:28][C@@H:29]([C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=1[N:38]1[N:42]=[CH:41][CH:40]=[N:39]1)[CH3:30].Cl>CO>[F:37][C:35]1[CH:34]=[CH:33][C:32]([N:38]2[N:42]=[CH:41][CH:40]=[N:39]2)=[C:31]([C@H:29]([O:28][C:3]2[CH:4]=[C:5]([C:8]3[CH:9]=[N:10][C:11]([O:14][CH:15]4[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]4)=[CH:12][CH:13]=3)[CH:6]=[N:7][C:2]=2[NH2:1])[CH3:30])[CH:36]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67468730tert-butyl 4-[(6'-amino-5'-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,3'-bipyridin-6-yl)oxy]piperidine-1-carboxylate

Product 1

HCID 545884465-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-6'-(piperidin-4-yloxy)-3,3'-bipyridin-6-amineYield 64.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the tert-butyl 4-[(6′-amino-5′-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,3′-bipyridin-6-yl)oxy]piperidine-1-carboxylate (115 mg, 0.2 mmol) in MeOH (1 mL) was added HCl (4N in dioxane, 1 mL). The mixture was stirred at room temperature for 1 hr. The mixture was concentrated and the residue purified by a reversed phase prep-HPLC. The desired fractions were lyophillized to give the title compound (61 mg) as an off-white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by a reversed phase prep-HPLC

Sources & evidence

ORD record
ord-7b9dccd79c254872b62b660105da099d
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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