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1,2-Dichloroethane → 5-(2-Fluoro-4-methylphenyl)-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]nicotinamide 1-oxide

HRID 1909150
Notes
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Reaction equation

HRID 1909150 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[N+:11]([O-:18])[CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=O.[CH3:19][C:20]1[N:24]=[C:23]([C@H:25]([NH2:27])[CH3:26])[O:22][N:21]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[N+:11]([O-:18])[CH:12]=[C:13]([CH:17]=1)[C:14]([NH:27][C@@H:25]([C:23]1[O:22][N:21]=[C:20]([CH3:19])[N:24]=1)[CH3:26])=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 28948822(R)-1-(3-Methyl-1,2,4-oxadiazol-5-yl)ethan-1-amineHCID 673383365-(2-Fluoro-4-methylphenyl)nicotinic acid 1-oxide

Product 1

HCID 46195076
5-(2-Fluoro-4-methylphenyl)-N-[(1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]nicotinamide 1-oxide
Yield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2-fluoro-4-methylphenyl)nicotinic acid 1-oxide (22.6 mg, 0.09 mmol) in DMF (0.5 mL) were added hydrochloride salt of (1R)-1-(3-methyl-1,2,4-oxadiazol-5-yl)ethanamine (23.8 mg, 0.12 mmol), EDC (26.3 mg, 0.14 mmol), HOBT (15.4 mg, 0.10 mmol) and diisopropylethylamine (64 μL, 0.37 mmol). The mixture was stirred at ambient temperature. After 72 h, 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 (18.4 mg). HRMS 357.1367 (M+1). 1H NMR (400 MHz, CDCl3): δ 9.02 (s, 1H); 8.73 (d, J=7.6 Hz, 1H); 8.53 (s, 1H); 7.98 (s, 1H); 7.32 (t, J=8.0 Hz, 1H); 7.08 (d, J=8.0 Hz, 1H); 7.02 (d, J=11.8 Hz, 1H); 5.60-5.51 (m, 1H); 2.42 (s, 3H); 2.29 (s, 3H); 1.80 (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-715ba09f4a784a25a8d7d728537c887a
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598209B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes