Triethylamine → HCID 59740593, compound

HRID 557532Notes

Reaction equation

HRID 557532 reaction equation
[NH2:1][C:2]1[C:3]([CH3:17])=[C:4]([C:8]2[CH:9]=[C:10]([Br:16])[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:25]([C:29]1[CH:37]=[CH:36][C:32]([C:33](Cl)=[O:34])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[Br:16][C:10]1[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=[C:8]([C:4]2[C:3]([CH3:17])=[C:2]([NH:1][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:29]([C:25]([CH3:27])([CH3:26])[CH3:28])=[CH:30][CH:31]=3)[CH:7]=[CH:6][CH:5]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743724-tert-Butylbenzoyl chlorideHCID 59740600HCID 59740600, compound

Product 1

HCID 59740593HCID 59740593, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 25-mL round bottomed flask was cooled to 0° C. with an ice/water bath and charged with 5-(3-amino-2-methylphenyl)-3-bromo-1-methylpyridin-2-one (12) (0.71 g, 2.20 mmol), triethylamine (489 mg, 4.84 mmol), methylene chloride (10 mL) and 4-tert-butyl-benzoyl chloride (0.48 g, 2.42 mmol) and the reaction mixture stirred at room temperature for 18 h. After this time the reaction was partitioned between water (25 mL) and ethyl acetate (50 mL). The organic layer was separated and washed with saturated aqueous sodium bicarbonate (2×25 mL), brine (50 mL) and dried over magnesium sulfate. The drying agent was removed by filtration and the filtrate concentrated under reduced pressure. The resulting residue was subjected to flash chromatography to afford 0.75 g (75%) of N-(3-(5-bromo-1-methyl-6-oxo-1,6-dihydropyridin-3-yl)-2-methylphenyl)-4-tert-butylbenzamide (13) as a white solid: mp 149-151° C.; 1H NMR (300 MHz, CDCl3) 7.87 (dd, 1H, J=2.4 Hz), 7.86 (d, 2H, J=8.4 Hz), 7.71 (br s, 1H), 7.54 (d, 2H, J=8.7 Hz), 7.30 (t, 1H, J=7.8 Hz), 7.27 (d, 1H, J=1.8 Hz), 3.75 (br s, 2H), 7.05 (dd, 1H, J=7.8, 1.5 Hz), 3.67 (s, 3H), 2.24 (s, 3H), 1.37 (s, 9H); MS (ESI+) m/z 453 (M+H).

Workup

  1. customAfter this time the reaction was partitioned between water (25 mL) and ethyl acetate (50 mL)
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium bicarbonate (2×25 mL), brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-d0dd3bedb60146f6a1e6503756720d19
Source dataset
uspto-grants-2011_11
Patent number
US08058446B2

Reaction notes

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