HCID 11719201, compound → HCID 59428581, compound

HRID 503824Notes

Reaction equation

HRID 503824 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][N:18]([C:21](=[O:32])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:31])([F:30])[F:29])[CH2:19][CH:20]=3)=[N:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1>CO.[Pd]>[CH:1]1([CH2:4][CH2:5][NH:6][C:7]([C:9]2[CH:10]=[CH:11][C:12]([CH:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:32])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:31])([F:29])[F:30])[CH2:17][CH2:16]3)=[N:13][CH:14]=2)=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 11719201HCID 11719201, compound

Product 1

HCID 59428581HCID 59428581, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 1′-(2-trifluoromethylbenzoyl)-1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl-5-carboxylic acid (2-cyclopropylethyl)amide (0.030 g, 0.068 mmol) in methanol (5 mL) was added Pd/C (0.010 g, 12 mol %). The mixture was placed under an atmosphere of hydrogen for 24 hours and then filtered through celite. The filtrate was concentrated in vacuo. The crude product was purified by column chromatography to yield the title compound in 50% yield (0.015 g). 1H NMR (300 MHz, CDCl3) δ 8.91 (s, 1H), 8.12-8.08 (m, 1H), 7.71-7.67 (m, 1H), 7.60-7.47 (m, 2H), 7.38 (d, J=7.5 Hz, 1H), 7.31-7.22 (m, 1H), 6.62 (s, 1H), 4.95-4.85 (m, 1H), 3.55-3.41 (m, 3H), 3.18-2.84 (m, 3H), 2.07-2.02 (m, 1H), 1.92-1.65 (m, 2H), 1.52-1.45 (dd, J=6.9 and 7.0 Hz, 2H), 0.71-0.66 (m, 1H), 0.46-0.44 (m, 2H), 0.07-0.04 (m, 2H). 13C NMR (CDCl3, 75 MHz) δ 167.4, 166.0, 165.2, 147.1, 146.9, 136.6, 136.5, 132.3, 132.2, 129.1, 127.2, 121.1, 120.8, 47.4, 44.0, 41.8, 40.4, 34.3, 31.5, 30.7, 8.6, 4.2. MS (ES+) m/z 446.1 (M+1).

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-0b23c09a771d4aa7a3a95453f24a7c30
Source dataset
uspto-grants-2010_08
Patent number
US07777036B2

Reaction notes

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