1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-[6-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-pyridin-2-yl]-N-(2-methoxy-5-nitrophenyl)-acetamide

HRID 1829705Notes

Reaction equation

HRID 1829705 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]([OH:21])=O)[CH:15]=[CH:14][CH:13]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1.CC[N:29]=C=NCCCN(C)C.[N+:38]([C:41]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][C:42]=1N)([O-:40])=[O:39].CC(C)=O.ClCCl>CN(C1C=CN=CC=1)C.ClCCl.CN(C=O)C>[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:29][C:46]4[CH:47]=[C:41]([N+:38]([O-:40])=[O:39])[CH:42]=[CH:44][C:45]=4[O:48][CH3:49])=[O:21])[CH:15]=[CH:14][CH:13]=3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 853005-Methoxy-2-nitroanilineHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 22054464HCID 22054464, compound

Product 1

HCID 220544612-[6-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-pyridin-2-yl]-N-(2-methoxy-5-nitrophenyl)-acetamideYield 12%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

[6-(9-Chloro-3-methyl-4-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), 2-Nitro-5-methoxyaniline (0.044 g, 0.26 mmol), DMAP (0.005 g, 0.04 mmol) in dichloromethane (4.5 ml) and DMF (0.75 ml) react for 5 h in a fashion similar to that of Example 3. Column chromatography (silica gel, acetone/dichloromethane gradient) gives the title compound (0.012 g, 12%). Mass Spectrum (FIA) (m/z) 520.2 [M+1]

Sources & evidence

ORD record
ord-a73b5c71d0b34e8dbb25ffc9ff8b340a
Source dataset
uspto-grants-2006_06
Patent number
US07064131B2

Reaction notes

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