1,2-Dichloroethane → 5-(4-Fluorophenyl)-1-(3-hydroxy-3-methylbutan-2-yl)-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-6-oxo-1,6-dihydropyridine-3-carboxamide

HRID 1909157Notes

Reaction equation

HRID 1909157 reaction equation
[Cl-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15](=[O:16])[N:14]([CH:17]([C:19]([OH:22])([CH3:21])[CH3:20])[CH3:18])[CH:13]=[C:12]([C:23]([OH:25])=O)[CH:11]=2)=[CH:6][CH:5]=1.Cl.[CH3:27][C:28]1[N:32]=[C:31]([C@H:33]([NH2:35])[CH3:34])[O:30][N:29]=1.C(Cl)CCl.ON1C2N=CC=CC=2N=N1.CN1CCOCC1>CN(C)C=O.O>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:15](=[O:16])[N:14]([CH:17]([C:19]([OH:22])([CH3:20])[CH3:21])[CH3:18])[CH:13]=[C:12]([C:23]([NH:35][C@@H:33]([C:31]3[O:30][N:29]=[C:28]([CH3:27])[N:32]=3)[CH3:34])=[O:25])[CH:11]=2)=[CH:8][CH:9]=1

Participants

9

Reactant 6

HCID 111,2-DichloroethaneHCID 5234Sodium ChlorideHCID 79724-MethylmorpholineHCID 181649HOAtHCID 66661266(R)-1-(3-Methyl-1,2,4-oxadiazol-5-yl)ethanamine hydrochlorideHCID 673376845-(4-Fluorophenyl)-1-(3-hydroxy-3-methylbutan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Product 1

HCID 461952185-(4-Fluorophenyl)-1-(3-hydroxy-3-methylbutan-2-yl)-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-6-oxo-1,6-dihydropyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the sodium chloride salt of 5-(4-fluorophenyl)-1-(3-hydroxy-3-methylbutan-2-yl)-6-oxo-1,6-dihydropyridine-3-carboxylic acid (177 mg, 0.46 mmol) in N,N-dimethylformamide (2 mL) were added (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine hydrochloride salt (110 mg, 0.55 mmol), EDC (105 mg, 0.55 mmol), 1-hydroxy-7-azabenzotriazole (6 mg, 0.05 mmol) and N-methylmorpholine (0.121 mL, 1.10 mmol). The reaction mixture was stirred at ambient temperature. After 18 h, water was added. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile→15% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound. HRMS 429.1973 (M+1).

Workup

  1. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile→15% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-e821e780665f4a34a58b92eeb19134aa
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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