Triethylamine → (6-{[3-(2-Chloro-6-fluorophenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-pyridin-2-yl)-acetic acid ethyl ester

HRID 1829702Notes

Reaction equation

HRID 1829702 reaction equation
CCN(CC)CC.[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:10]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[C:29]1[C:33]([C:34](Cl)=[O:35])=[C:32]([CH3:37])[O:31][N:30]=1>ClCCl>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:34]([C:33]2[C:29]([C:23]3[C:24]([F:28])=[CH:25][CH:26]=[CH:27][C:22]=3[Cl:21])=[N:30][O:31][C:32]=2[CH3:37])=[O:35])[N:10]=1)[CH3:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chlorideHCID 13060163Ethyl (6-aminopyridin-2-yl)acetate

Product 1

HCID 69632684(6-{[3-(2-Chloro-6-fluorophenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-pyridin-2-yl)-acetic acid ethyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add Et3N (0.7 ml, 5.06 mmol) to a solution of ethyl 2-(2-Aminopyridin-6-yl)acetate (for preparation see Goto, Jiro; Sakane, Kazuo; Nakai, Yoshiharu; Teraji, Tsutomu; Kamiya, Takashi. J. Antibiot. (1984), 37(5), 532–45) (0.6 g, 3.33 mmol) and 3-(2-chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl chloride (0.694 g, 2.53 mmol) in dichloromethane (7 ml) and stir overnight. Dilute the reaction with dichloromethane, wash (H2O then brine), dry (MgSO4), filter, and concentrate. Column chromatography (silica gel, hexanes/EtOAc gradient) gives the title compound (0.81 g, 77%). Mass Spectrum (FIA) (m/z) 418.2 [M+1]

Workup

  1. additionDilute
  2. washwash (H2O
  3. dry with materialbrine), dry (MgSO4)
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-a840cfa73bd44afd8f7330c6cd186f34
Source dataset
uspto-grants-2006_06
Patent number
US07064131B2

Reaction notes

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