N-bromobutanimide → HCID 10216350, compound

HRID 1867015Notes

Reaction equation

HRID 1867015 reaction equation
[CH3:1][N:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3](=[O:19])[O:4][C:5]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:18])[CH:6]=1.[Br:26]N1C(=O)CCC1=O>C(Cl)Cl>[CH3:1][N:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:3](=[O:19])[O:4][C:5]1[CH:10]=[CH:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7](=[O:18])[C:6]=1[Br:26]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22050484HCID 22050484, compound

Product 1

HCID 10216350HCID 10216350, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyl-2-oxo-1,2-dihydropyridin-4-yl methyl(phenyl)carbamate (0.38 g, 1.13 mmol) in anhydrous CH2Cl2 (7 mL) was added N-Bromosuccinimide (NBS, 0.24 g, 1.34 mmol). The reaction was stirred overnight at room temperature under nitrogen atmosphere. The reaction mixture was purified by flash chromatography (silica gel) using ethyl acetate/hexane (1:1 v/v). The appropriate fractions were collected according to ES MS (M+H 413) and concentrated. The dried product showed about 14% of di-bromonated product by analytical HPLC. The compounds were separated by reverse phase HPLC using a 10-90% acetonitrile in water (30 minute gradient) at a 100 mL/min flow rate to afford (after lyophilization) the salt of the desired compound. The salt was diluted in ethyl acetate and washed with NaHCO3. The organic extracts were dried over anhydrous Na2SO4 and concentrated to afford the desired compound (0.271 g, 58%) as a beige solid. 1H-NMR (d6-DMSO, 400 MHz) δ7.94 (d, 1H, J=7.2 Hz), 7.29 (m, 10H), 6.48 (s, 1H), 5.12 (s, 2H), 3.33 (s, 3H); ES-HRMS m/z 413.0495 (M+H calculated for C20H18O3Br requires 413.0496).

Workup

  1. customThe reaction mixture was purified by flash chromatography (silica gel)
  2. customThe appropriate fractions were collected
  3. concentrationconcentrated
  4. customThe compounds were separated by reverse phase HPLC
  5. customa 10-90% acetonitrile in water (30 minute gradient)

Sources & evidence

ORD record
ord-a402de5bf8a84d18874ce291fcbaca40
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

Loading…