Triethylamine → HCID 59580613, compound

HRID 533292Notes

Reaction equation

HRID 533292 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][NH:5][C:6]([C:8]1[C:9](Cl)=[N:10][CH:11]=[C:12]([F:14])[CH:13]=1)=[O:7].CCN(CC)CC>CO.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][CH:11]=[C:12]([F:14])[CH:13]=1)=[O:7]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 59580936HCID 59580936, compound

Product 1

HCID 59580613HCID 59580613, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of [(2-chloro-5-fluoropyridine-3-carbonyl)-amino]-acetic acid methyl ester (4.65 g, 18.9 mmol) in methanol (200 mL) in a Parr vessel was added Et3N (3.15 mL, 22.6 mmol) and palladium hydroxide on carbon (1.5 g, 20 wt % Pd, moisture 60%). The vessel was evacuated and then put under an atmosphere of hydrogen (initial pressure 42 psi). After 5 min the hydrogen pressure was 14 psi. The catalyst was removed via suction filtration over Celite® and then the filtrate was concentrated. Purification by silica gel chromatography (0 to 100% ethyl acetate/hexanes) afforded a light yellow solid (3.83 g, 95%): mp 80-82° C.; 1H NMR (300 MHz, CDCl3) δ 8.84 (s, 1H), 8.62 (d, J=2.7 Hz, 1H), 7.87 (m, 1H), 7.00 (br s, 1H), 4.27 (d, J=5.3 Hz, 2H), 3.82 (s, 3H); ESIMS m/z 213 (M+1).

Workup

  1. customThe vessel was evacuated
  2. customThe catalyst was removed via suction filtration over Celite®
  3. concentrationthe filtrate was concentrated
  4. customPurification by silica gel chromatography (0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-3dbd7ce49e454f6d9ff3a6921649491a
Source dataset
uspto-grants-2014_10
Patent number
US08853246B2

Reaction notes

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