Triethylamine → N-[4-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]2-(3,4,5-trimethoxy-phenyl)-acetamide

HRID 1838455Notes

Reaction equation

HRID 1838455 reaction equation
[NH2:1][CH:2]1[CH2:6][CH:5]([N:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([Cl:17])[C:11]=3[C:10]3=[N:18][O:19][C:20]([CH3:21])=[C:9]3[C:8]2=[O:22])[CH:4]=[CH:3]1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH2:35][C:36](O)=[O:37])[CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32].CCN(CC)CC.CCN=C=NCCCN(C)C>C(Cl)Cl>[Cl:17][C:12]1[C:11]2[C:10]3[C:9](=[C:20]([CH3:21])[O:19][N:18]=3)[C:8](=[O:22])[N:7]([CH:5]3[CH2:6][CH:2]([NH:1][C:36](=[O:37])[CH2:35][C:27]4[CH:28]=[C:29]([O:33][CH3:34])[C:30]([O:31][CH3:32])=[C:25]([O:24][CH3:23])[CH:26]=4)[CH:3]=[CH:4]3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 703723,4,5-Trimethoxyphenylacetic acidHCID 120949645-(4-amino-cyclopent-2-enyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one

Product 1

HCID 22714093N-[4-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclopent-2-enyl]2-(3,4,5-trimethoxy-phenyl)-acetamideYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-(4-amino-cyclopent-2-enyl)-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (47 mg, 0.15 mmol) in CH2Cl2 (2.5 mL) was added 3,4,5-trimethoxy phenyl acetic acid (45 mg, 0.20 mmol), Et3N (0.053 mL, 0.38 mmol) and EDCI (38 mg, 0.20 mmol) and stirred at r.t. for 18 hours. The mixture was diluted with CH2Cl2, washed (brine), dried (Na2SO4), filtered and concentrated. Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave the title compound (23 mg, 29%). Mass Spectrum (FIA) (m/z) 522.2 (M−1). 1H NMR (CDCl3): δ 7.43 (d, 1H); 7.37 (m, 2H); 6.42 (s, 2H); 5.88 (m, 2H); 5.18 (m, 1H); 3.78 (s, 9H); 3.47 (s, 2H); 2.90 (m, 2H); 1.98 (m, 2H).

Workup

  1. washwashed (brine)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1fb0acd523264a77ab5591c9db4f6e33
Source dataset
uspto-grants-2004_01
Patent number
US06673809B2

Reaction notes

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