Potassium Carbonate → 1-(6-amino-3'-fluoro-5-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,4'-bipyridin-2'-yl)azetidin-3-ol

HRID 1406324Notes

Reaction equation

HRID 1406324 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:10]=[N:11][C:12]([NH2:30])=[C:13]([O:15][C@@H:16]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[N:25]3[N:29]=[CH:28][CH:27]=[N:26]3)[CH3:17])[CH:14]=2)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl.[OH:38][CH:39]1[CH2:42][NH:41][CH2:40]1>CS(C)=O>[NH2:30][C:12]1[N:11]=[CH:10][C:9]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([N:41]3[CH2:42][CH:39]([OH:38])[CH2:40]3)[C:7]=2[F:8])=[CH:14][C:13]=1[O:15][C@@H:16]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[N:25]1[N:26]=[CH:27][CH:28]=[N:29]1)[CH3:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27592903-Hydroxyazetidine hydrochlorideHCID 674669252',3'-difluoro-5-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,4'-bipyridin-6-amine

Product 1

HCID 545885431-(6-amino-3'-fluoro-5-{(1R)-1-[5-fluoro-2-(2H-1,2,3-triazol-2-yl)phenyl]ethoxy}-3,4'-bipyridin-2'-yl)azetidin-3-olYield 30%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2′,3′-Difluoro-5-[(R)-1-(5-fluoro-2-[1,2,3]triazol-2-yl-phenyl)-ethoxy-[3,4′]bipyridinyl-6-ylamine (example 129) (35 mg, 0.085 mmol, 1.0 eq) and potassium carbonate (115 mg, 0.833 mmol, 9.8 eq) and 3-hydroxyazetidine hydrochloride (91.3 mg, 0.833 mmol, 9.8 eq) in anhydrous DMSO (2 mL) were microwaved for 10 min. at 150° C. The mixture was filtered, concentrated, and purified with a reverse phase pre-HPLC under acidic condition to give the title compound (11.8 mg, 30% yield) as a amorphous solid after lyophilization.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified with a reverse phase pre-HPLC under acidic condition

Sources & evidence

ORD record
ord-97ad367bd4c4492ea651ceb533b61456
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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