Thionyl Chloride → HCID 89813997, compound

HRID 525409Notes

Reaction equation

HRID 525409 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1([CH3:28])[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[C:14]([CH3:21])[CH:13]=2)[C@H:7]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(Cl)Cl>[CH3:5][C:6]1([CH3:28])[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([Cl:3])=[O:17])=[C:14]([CH3:21])[CH:13]=2)[C@H:7]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 89813479HCID 89813479, compound

Product 1

HCID 89813997HCID 89813997, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

Thionyl chloride (0.287 mL, 3.93 mmol) was added to a solution of (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-2-methylbenzoic acid (0.128 g, 0.393 mmol) in DCM (2.5 mL) and the mixture was heated at 40° C. for 1 hour. The reaction mixture was concentrated to afford (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-2-methylbenzoyl chloride as a yellow-orange solid. The yellow-orange solid was dissolved in DCM (2.5 mL) and the solution was cooled to 0° C. 1,5-Naphthyridin-4-amine (commercially available from Astatech Inc., Bristol, Pa.) (0.063 g, 0.433 mmol) and N,N-diisopropylethylamine (0.144 mL, 0.826 mmol) were added and the ice bath was removed. The resulting reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was then concentrated and the residue was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 50-100% EtOAc-hexane) to afford (S)-4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)-2-methyl-N-(1,5-naphthyridin-4-yl)benzamide (0.070 g, 0.155 mmol, 39% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 3H), 1.65 (s, 3H), 2.44 (s, 3H), 5.54 (s, 1H), 7.17-7.51 (m, 6H), 7.61 (d, J=2.15 Hz, 1H), 7.67 (d, J=8.51 Hz, 1H), 7.86 (dd, J=8.56, 4.16 Hz, 1H), 8.44 (dd, J=8.56, 1.61 Hz, 1H), 8.54 (d, J=5.09 Hz, 1H), 8.81-9.09 (m, 2H), 10.31 (s, 1H). m/z (ESI) 453 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-97d6b104b20046179ab9023afae037e3
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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