1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3,4,5-trimethoxyphenyl)-3-(5-phenyl-3-(2-chloro-6-fluoro-phenyl)isoxazol-4-oyl)aminophenyl Acetamide

HRID 434035

Reaction equation

HRID 434035 reaction equation
[C:1]([C:4]1[C:5]([C:15]2[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:22])=[N:6][O:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:3])=O.[NH2:23][C:24]1[CH:25]=[C:26]([CH2:30][C:31]([NH:33][C:34]2[CH:39]=[C:38]([O:40][CH3:41])[C:37]([O:42][CH3:43])=[C:36]([O:44][CH3:45])[CH:35]=2)=[O:32])[CH:27]=[CH:28][CH:29]=1.CCN=C=NCCCN(C)C>ClCCl.CN(C1C=CN=CC=1)C>[CH3:41][O:40][C:38]1[CH:39]=[C:34]([NH:33][C:31](=[O:32])[CH2:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([NH:23][C:1]([C:4]3[C:5]([C:15]4[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:22])=[N:6][O:7][C:8]=3[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)=[O:3])[CH:25]=2)[CH:35]=[C:36]([O:44][CH3:45])[C:37]=1[O:42][CH3:43]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 18756260HCID 18756260, compoundHCID 187562674-Carboxy-5-phenyl-3-(2-chloro-6-fluorophenyl)isoxazole

Product 1

HCID 60083770N-(3,4,5-trimethoxyphenyl)-3-(5-phenyl-3-(2-chloro-6-fluoro-phenyl)isoxazol-4-oyl)aminophenyl AcetamideYield 64.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-carboxy-5-phenyl-3-(2-chloro-6-fluorophenyl)isoxazole (0.135 g, 0.425 mmol) and 2-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamide (0.129 g, 0.408 mmol) in dichloromethane (5 ml) was added EDCI (0.082 g, 0.51 mmol) and DMAP (0.062 g, 0.51 mmol) and stirred for 14 h. The mixture was applied to a silica gel chromatography column. Elution with hexanes and ethyl acetate (gradient) gave the title compound (0.162 g, 64%).

Workup

  1. washElution with hexanes and ethyl acetate (gradient)

Sources & evidence

ORD record
ord-b16f705797594b3eb3fb7adba1cb9f18
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Linked notes

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