Diisopropylethylamine → N-[3-fluoro-4-(1-piperidinyl)phenyl]-4-(2-pyridinyl)benzamide

HRID 1822922Notes

Reaction equation

HRID 1822922 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][CH:8]=1.CCN(C(C)C)C(C)C.[F:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:32]=1[N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[NH2:29]>O1CCCC1>[F:25][C:26]1[CH:27]=[C:28]([NH:29][C:11](=[O:12])[C:10]2[CH:14]=[CH:15][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:8][CH:9]=2)[CH:30]=[CH:31][C:32]=1[N:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 64857583-Fluoro-4-(piperidin-1-yl)anilineHCID 120170524-(2-Pyridinyl)benzoyl Chloride

Product 1

HCID 11176305N-[3-fluoro-4-(1-piperidinyl)phenyl]-4-(2-pyridinyl)benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Pyrid-2-yl)benzoyl chloride (1.37 mmol, prepared as described in Example 1B, and DIEA (1.2 mL, 6.9 mmol) in tetrahydrofuran (5 mL) were treated with the product from Example 10B (260 mg, 1.34 mmol). The mixture was stirred overnight at room temperature and concentrated under reduced pressure. The residue was taken up in ethyl acetate (50 mL), washed with H2O (3×15 mL) and brine (15 mL), dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The residue was triturated with 3:2 hexanes:ethyl acetate to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.32 (s, 1H), 8.72 (d, J=4.7 Hz, 1H), 8.25 (d, J=8.2 Hz, 2H), 8.05–8.10 (m, 3H), 7.94 (td, J=7.8 Hz, 1.7 Hz, 1H), 7.70 (dd, J=14.9 Hz, 2.4 Hz, 1H), 7.40–7.50 (m, 2H), 7.04 (t, J=9.4 Hz, 1H), 2.92–2.96 (m, 4H), 1.62–1.69 (m, 4H), 1.52–1.56 (m, 2H); MS (ESI+) m/z 376 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washwashed with H2O (3×15 mL) and brine (15 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was triturated with 3:2 hexanes

Sources & evidence

ORD record
ord-3918092d83e249aea0b2253265cd0d5d
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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