Diisopropylethylamine → 3-(4-Fluorophenyl)-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-2-oxo-2H-1,2'-bipyridine-5-carboxamide

HRID 1909153Notes

Reaction equation

HRID 1909153 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:23])[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:11]=[C:12]([C:14](O)=[O:15])[CH:13]=2)=[CH:4][CH:3]=1.[CH3:24][C:25]1[N:29]=[C:28]([C@H:30]([NH2:32])[CH3:31])[O:27][N:26]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:23])[N:10]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[CH:11]=[C:12]([C:14]([NH:32][C@@H:30]([C:28]3[O:27][N:26]=[C:25]([CH3:24])[N:29]=3)[CH3:31])=[O:15])[CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 28948822(R)-1-(3-Methyl-1,2,4-oxadiazol-5-yl)ethan-1-amineHCID 673393723-(4-Fluorophenyl)-2-oxo-2H-1,2'-bipyridine-5-carboxylic acid

Product 1

HCID 461952173-(4-Fluorophenyl)-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-2-oxo-2H-1,2'-bipyridine-5-carboxamideYield 95.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-fluorophenyl)-2-oxo-2H-1,2′-bipyridine-5-carboxylic acid (20.0 mg, 0.05 mmol) in DMF (0.5 mL) were added hydrochloride salt of (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine (13.6 mg, 0.07 mmol), HATU (0.5 M in DMF; 0.16 mL, 0.08 mml) and diisopropylethylamine (36 μL, 0.21 mmol). The mixture was stirred at ambient temperature. After 30 min, the mixture was purified by reverse chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) to give the title compound (20 mg). HRMS 420.1470 (M+1). 1H NMR (400 MHz, CDCl3): δ 8.62 (d, J=4.8 Hz, 1H); 8.53 (d, J=2.5 Hz, 1H); 7.94-7.83 (m, 3H); 7.70 (dd, J=8.3, 5.4 Hz, 2H); 7.41 (t, J=5.8 Hz, 1H); 7.12 (t, J=8.5 Hz, 2H); 6.66 (d, J=7.7 Hz, 1H); 5.60-5.51 (m, 1H); 2.40 (s, 3H); 1.69 (d, J=7.1 Hz, 3H).

Workup

  1. customthe mixture was purified by reverse chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-ba771743632144389c79c5ec84eb7080
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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