Triethylamine → N-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl)benzamide

HRID 1822931Notes

Reaction equation

HRID 1822931 reaction equation
[Cl:1][C:2]1[C:3]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[C:17]([C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[C:17]([C:21]1[CH:22]=[CH:23][C:24]([NH:25][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=3)=[CH:16][CH:15]=2)=[CH:26][CH:27]=1)([CH3:20])([CH3:18])[CH3:19]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 698614-Tert-ButylanilineHCID 757711-HydroxybenzotriazoleHCID 221704544-(3-Chloropyridin-2-yl)benzoic acid

Product 1

HCID 11451387N-(4-tert-butylphenyl)-4-(3-chloropyridin-2-yl)benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

The product from Example 24A (75.0 mg, 0.321 mmol), 4tert-butylaniline (61 μL, 0.383 mmol), PS-DCC (1.35 mmol/g, 0.7132 g, 0.963 mmol), HOBT (44.0 mg, 0.326 mmol), and triethylamine (0.13 mL, 0.93 mmol) in DMF (3 mL) were combined and heated at 55° C. for 16 hours. The mixture was allowed to cool to room temperature, filtered, and the filtrate was diluted with diethyl ether (20 mL). The diethyl ether was washed with 1N HCl (15 mL), brine (15 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (30% ethyl acetate in hexanes) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ 8.63 (dd, 1H), 7.98 (d, 2H), 7.88 (d, 2H), 7.88 (d, 1H), 7.81 (br s, 1H), 7.59 (d, 2H), 7.41 (d, 2H), 7.29 (dd, 1H), 1.33 (s, 9H); MS (m/z) 365.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. additionthe filtrate was diluted with diethyl ether (20 mL)
  4. washThe diethyl ether was washed with 1N HCl (15 mL), brine (15 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fceefcf870e6458d8cb225c6303b565a
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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