3-Methoxyaniline → 2-[6-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-pyridin-2-yl]-N-(3-methoxyphenyl)-acetamide

HRID 1829706Notes

Reaction equation

HRID 1829706 reaction equation
[Cl:1][C:2]1[C:3]2[C:4]3[C:5](=[C:23]([CH3:26])[O:24][N:25]=3)[C:6](=[O:22])[N:7]([C:12]3[N:17]=[C:16]([CH2:18][C:19](O)=[O:20])[CH:15]=[CH:14][CH:13]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1.CCN=C=NCCCN(C)C.[CH3:38][O:39][C:40]1[CH:41]=[C:42]([CH:44]=[CH:45][CH:46]=1)[NH2:43].CC(C)=O.ClCCl>CN(C1C=CN=CC=1)C.ClCCl>[Cl:1][C:2]1[C:3]2[C:4]3[C:5](=[C:23]([CH3:26])[O:24][N:25]=3)[C:6](=[O:22])[N:7]([C:12]3[N:17]=[C:16]([CH2:18][C:19]([NH:43][C:42]4[CH:44]=[CH:45][CH:46]=[C:40]([O:39][CH3:38])[CH:41]=4)=[O:20])[CH:15]=[CH:14][CH:13]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 108243-MethoxyanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 22054464HCID 22054464, compound

Product 1

HCID 220544632-[6-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-pyridin-2-yl]-N-(3-methoxyphenyl)-acetamideYield 53%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

[6-(9-Chloro-3-methyl4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-pyridin-2-yl]-acetic acid (0.075 g, 0.2 mmol), EDCI (0.055 g, 0.3 mmol), 3-methoxyaniline (0.03 ml, 0.26 mmol), DMAP (0.005 g, 0.04 mmol) in dichloromethane (4.5 ml) and DMP (0.75 ml) react for 5.5 h in a fashion similar to that of Example 3. Column chromatography (silica gel, acetone/dichloromethane gradient) gives the title compound (0.05 g, 53%).

Sources & evidence

ORD record
ord-005a0bd6eaa14913a5599eb832f29dc9
Source dataset
uspto-grants-2006_06
Patent number
US07064131B2

Reaction notes

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