Pyridine → HCID 10362522, compound

HRID 2213363Notes

Reaction equation

HRID 2213363 reaction equation
[F:1][CH:2]([F:6])[C:3](O)=[O:4].Cl.[NH2:8][CH2:9][CH:10]1[O:14][C:13](=[O:15])[N:12]([C:16]2[CH:21]=[CH:20][C:19]([N:22]3[CH:27]=[CH:26][C:25](=[O:28])[CH2:24][CH2:23]3)=[C:18]([F:29])[CH:17]=2)[CH2:11]1.N1C=CC=CC=1.C(N=C=NC(C)C)(C)C>CN(C=O)C>[F:29][C:18]1[CH:17]=[C:16]([N:12]2[CH2:11][CH:10]([CH2:9][NH:8][C:3](=[O:4])[CH:2]([F:6])[F:1])[O:14][C:13]2=[O:15])[CH:21]=[CH:20][C:19]=1[N:22]1[CH:23]=[CH:24][C:25](=[O:28])[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 9788Difluoroacetic acidHCID 12734DiisopropylcarbodiimideHCID 21957342HCID 21957342, compound

Product 1

HCID 10362522HCID 10362522, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Difluoroacetic acid (0.031 mL, 0.48 mmol) is added to a solution of 1-[4-(5-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-phenyl]-2,3-dihydro-1H-pyridin-4-one hydrochloride (0.150 g, 0.44 mmol) in DMF (1.5 mL) with pyridine (0.071 mL, 0.88 mmol), followed by addition of diisopropylcarbodiimide (0.076 mL, 0.48 mmol). The mixture is stirred at r.t. for 1 h. Most of the solvent is removed under high vacuum, and the product is purified by silica gel column chromatography (eluent: 2% MeOH in DCM). The chromatography is repeated (eluent: 1% MeOH in DCM) to afford N-{3-[3-Fluoro-4-(4-oxo-3,4-dihydro-2H-pyridin-1-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl} difluoroacetamide as a white solid. Yield 0.065 g (39%). MS (m/z): 384 [M+H]+. 1H NMR (300 MHz, DMSO-d6) δ 9.36 (t, J=5.5 Hz, 1H), 7.82–7.49 (m, 4H), 6.44 (t, J=53.6 Hz, 1H), 5.18 (d, J=7.7 Hz, 1H), 5.03–4.98 (m, 1H), 4.38–4.32 (m, 1H), 4.07 (t, J=7.4 Hz, 2H), 3.97 (dd, J=6.3 and 9.3 Hz, 1H), 3.72 (t, J=5.5 Hz, 1H), 3.51–3.49 (m, 2H), 2.69–2.64 (m, 2H).

Workup

  1. customMost of the solvent is removed under high vacuum
  2. customthe product is purified by silica gel column chromatography (eluent: 2% MeOH in DCM)

Sources & evidence

ORD record
ord-571abee4dd6842eea545b5ff7c385b8f
Source dataset
uspto-grants-2006_09
Patent number
US07105547B2

Reaction notes

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