Dimethyl Sulfoxide → ((1S,3R)-3-(5'-chloro-6-(3-fluorobenzylamino)-2,4'-bipyridin-2'-yl-amino)cyclopentyl)methanol
Reaction equation
[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[N:10]=2)=[CH:4][C:5](F)=[N:6][CH:7]=1.CS(C)=O.[NH2:28][C@@H:29]1[CH2:33][CH2:32][C@H:31]([CH2:34][OH:35])[CH2:30]1>CCOC(C)=O>[Cl:1][C:2]1[C:3]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[N:10]=2)=[CH:4][C:5]([NH:28][C@@H:29]2[CH2:33][CH2:32][C@H:31]([CH2:34][OH:35])[CH2:30]2)=[N:6][CH:7]=1Participants
5
Procedure
To 5′-chloro-2′-fluoro-N-(3-fluorobenzyl)-2,4′-bipyridin-6-amine (100 mg, 0.301 mmol) was added DMSO (1 ml), ((1S,3R)-3-aminocyclopentyl)methanol (104 mg, 0.903 mmol) and TEA (0.21 ml, 1.51 mmol). The crude mixture was stirred at 100° C. for 20 hours, followed by LCMS. The crude reaction mixture was cooled, was diluted with EtOAc (60 mL), washed H2O (60 mL×2), brine (60 mL), dried over Na2SO4, and reduced. The crude was adsorbed onto silica gel, and purified by silica gel chromatography, 40-80% EtOAc/Heptane, 12 g ISCO silica column, resulting in ((1S,3R)-3-(5′-chloro-6-(3-fluorobenzylamino)-2,4′-bipyridin-2′-yl-amino)cyclopentyl)methanol (101 mg, 0.237 mmol). LCMS (m/z): 427.1 (MH+). retention time=0.69 min.
Workup
- customThe crude reaction mixture
- temperaturewas cooled
- washwashed H2O (60 mL×2), brine (60 mL)
- dry with materialdried over Na2SO4
- custompurified by silica gel chromatography, 40-80% EtOAc/Heptane, 12 g ISCO silica column
Sources & evidence
- ORD record
- ord-f96a41b5fbdc4cb2a38072a7b88fc122
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778951B2
Reaction notes
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