Tetrahydrofuran → Ethyl 3-(5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinamido)propanoate
Reaction equation
CN(C([O:8]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:25]1[CH2:29][O:28][CH2:27][CH2:26]1.[Br:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=2[C:46]2[CH:47]=[CH:48][C:49]([C:52]([OH:54])=O)=[N:50][CH:51]=2)=[CH:33][C:32]=1[F:55].CC[N:58]([CH:62](C)C)C(C)C>CCOC(C)=O>[Br:30][C:31]1[CH:36]=[CH:35][C:34]([NH:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([F:45])=[CH:41][C:40]=2[C:46]2[CH:47]=[CH:48][C:49]([C:52]([NH:58][CH2:62][CH2:26][C:27]([O:28][CH2:29][CH3:25])=[O:8])=[O:54])=[N:50][CH:51]=2)=[CH:33][C:32]=1[F:55]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Solid HATU (227 mg, 0.60 mmol) was added to a THF solution (4.8 mL) of 5-(2-(((4-bromo-3-fluorophenyl)amino)methyl)-5-fluorophenyl)picolinic acid (250 mg, 0.60 mmol), i-Pr2NEt (0.31 mL, 1.79 mmol), and (3-alanine ethyl ester hydrochloride (96 mg, 0.63) and the resulting mixture was stirred at room temperature. After 16 h the resulting mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.
Workup
- washwashed with water and brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- custompurified via column chromatography
Sources & evidence
- ORD record
- ord-0be1920eced241659f50e3699792b44f
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748624B2
Reaction notes
Loading…