Triethylamine → HCID 10308753, compound

HRID 896149Notes

Reaction equation

HRID 896149 reaction equation
[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][C:10]([N:12]3[CH2:16][C@H:15]([C:17]([NH2:19])=[O:18])[O:14][C:13]3=[O:20])=[CH:11][C:6]=2[O:5][CH2:4][C:3]1=[O:21].[F:22][CH2:23][CH2:24]N.Cl.C(N(CC)CC)C>CO>[F:22][CH2:23][CH2:24][NH:19][C:17]([C@@H:15]1[O:14][C:13](=[O:20])[N:12]([C:10]2[CH:9]=[CH:8][C:7]3[N:2]([CH3:1])[C:3](=[O:21])[CH2:4][O:5][C:6]=3[CH:11]=2)[CH2:16]1)=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 10149461HCID 10149461, compound

Product 1

HCID 10308753HCID 10308753, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred suspension of (5R)-3-(3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazin-7-yl)-2-oxo-oxazolidine-5-carboxylic acid methyl ester (EXAMPLE 59, Step 3, 200 mg, 0.65 mmol) in MeOH (7.5 mL) is added FCH2CH2NH2.HCl (325 mg, 3.25 mmol). To this resulting suspension is added triethylamine (453 μL, 3.25 mmol), and the solution is heated to 55° C. for 5 h followed by stirring for 16 h at room temperature. The reaction mixture is then concentrated to dryness under reduced pressure and the residue is purified by silica gel column chromatography (eluent: EtOAc) to give the title compound (153 mg, 63%); 1H NMR (300 MHz, DMSO) δ 8.68 (br t, 1H), 7.30 (d, 1H), 7.22-7.14 (m, 2H), 5.08 (dd, 1H), 4.65 (s, 2H), 4.54 (dd, 1H), 4.38 (t, 1H), 4.26 (t, 1H), 3.45 (s, 3H), 3.96 (dd, 1H), 3.50-3.35 (m, 5H); MS for C15H16FN3O5 m/z 338.5 (M+H)+.

Workup

  1. concentrationThe reaction mixture is then concentrated to dryness under reduced pressure
  2. customthe residue is purified by silica gel column chromatography (eluent: EtOAc)

Sources & evidence

ORD record
ord-17b5ebb84a8b4bf7828b0b3c70c94427
Source dataset
uspto-grants-2005_07
Patent number
US06919329B2

Reaction notes

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