Triethylamine → (3-{[3-(2-Chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-cycloheptyl)-acetic acid methyl ester

HRID 352214Notes

Reaction equation

HRID 352214 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:3]1.[Cl:14][C:15]1[C:20]([C:21]2[C:25]([C:26](Cl)=[O:27])=[C:24]([CH3:29])[O:23][N:22]=2)=[C:19]([F:30])[CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>ClCCl>[CH3:13][O:12][C:10](=[O:11])[CH2:9][CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:2]([NH:1][C:26]([C:25]2[C:21]([C:20]3[C:19]([F:30])=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:14])=[N:22][O:23][C:24]=2[CH3:29])=[O:27])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chlorideHCID 22714191Methyl 2-(3-aminocycloheptyl)acetate

Product 1

HCID 69849379(3-{[3-(2-Chloro-6-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-cycloheptyl)-acetic acid methyl esterYield 873.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.4 g (24 mmol) of methyl 2-(3-aminocycloheptyl)acetate, 0.03 g (0.46 mmol) of 3-(6-chloro-2-fluorophenyl)-5-methylisoxazole4-carbonyl chloride, and 0.07 ml (0.5 mmol) of triethylamine in dichloromethane (10 ml) was stirred for 12 hours. The solvent was removed in vacuo and replaced with ethyl acetate. The organic layer was washed with 1N HCl, then aq. NaHCO3, followed by brine and dried. The solvent was removed in vacuo then chromatographed on silica gel with hexane/EtOAc 3/1 to yield 1.7 g of the title compound. MS(ES+)m/z=423.

Workup

  1. customThe solvent was removed in vacuo
  2. washThe organic layer was washed with 1N HCl
  3. customdried
  4. customThe solvent was removed in vacuo
  5. customthen chromatographed on silica gel with hexane/EtOAc 3/1

Sources & evidence

ORD record
ord-2d4a1325369d4fb18de71cce0a4a9d19
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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