Triethylamine → HCID 11719201, compound

HRID 503823Notes

Reaction equation

HRID 503823 reaction equation
[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH2:16][CH2:17][NH:18][CH2:19][CH:20]=3)=[N:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:31]=[CH:30][CH:29]=[CH:28][C:24]=1[C:25](Cl)=[O:26].C(N(CC)CC)C>ClCCl>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH2:16][CH2:17][N:18]([C:25](=[O:26])[C:24]4[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=4[C:22]([F:21])([F:32])[F:33])[CH2:19][CH:20]=3)=[N:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 86617865HCID 86617865, compound

Product 1

HCID 11719201HCID 11719201, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1′,2′,3′,6′-tetrahydro[2,4′]bipyridinyl-5-carboxylic acid (2-cyclopropylethyl)amide (0.050 g, 0.184 mmol) in dichloromethane (5.0 mL) was added 2-(trifluoromethyl)benzoyl chloride (32 μL, 0.203 mmol), and triethylamine (31 μL, 0.203 mmol). The resulting mixture was stirred at room temperature for 30 minutes. The organic phase was washed with water (5 mL), saturated NaCl (5 mL), dried over MgSO4 and then concentrated in vacuo. The crude product was purified by column chromatography to afford the pure title compound in 42% yield (0.453 g). 1H NMR (300 MHz, CDCl3) δ 8.88 (s, 1H), 8.09 (d, J=8.3 Hz, 1H), 7.73-7.67 (m, 1H), 7.63-7.51 (m, 3H), 7.46-7.41 (m, 1H), 7.38-7.32 (m, 1H), 6.77 (s, 1H), 6.49-6.43 (m, 1H), 4.70-4.43 (m, 1H), 4.33-4.26 (m, 1H), 4.15-4.06 (m, 1H), 3.96-3.88 (m, 1H), 3.56-3.49 (dd, J=6.7 and 6.3 Hz, 2H), 3.47-3.30 (m, 2H), 2.76-2.60 (m, 2H), 1.54-1.47 (dd, J=6.8 and 7.0 Hz, 2H), 0.74-0.66 (m, 1H), 0.49-0.44 (m, 2H), 0.10-0.045 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 167.7, 165.3, 158.8, 147.2, 135.6, 134.7, 132.3, 129.3, 128.6, 127.2, 127.1, 125.4, 124.3, 118.6, 60.4, 47.1, 43.9, 42.3, 40.4, 34.3, 25.9, 8.6, 4.2. MS (ES+) m/z 444.0 (M+1).

Workup

  1. washThe organic phase was washed with water (5 mL), saturated NaCl (5 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-10c4b89d306d433898237346d5c356f4
Source dataset
uspto-grants-2010_08
Patent number
US07777036B2

Reaction notes

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