1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-(3,4,5-Trimethoxyphenyl)-3-(5-methyl-3-(2,6-difluoro-phenyl)isoxazol-4-oyl)aminophenyl Acetamide

HRID 434040Notes

Reaction equation

HRID 434040 reaction equation
[C:1]([C:4]1[C:5]([C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[F:17])=[N:6][O:7][C:8]=1[CH3:9])([OH:3])=O.[NH2:18][C:19]1[CH:20]=[C:21]([CH2:25][C:26]([NH:28][C:29]2[CH:34]=[C:33]([O:35][CH3:36])[C:32]([O:37][CH3:38])=[C:31]([O:39][CH3:40])[CH:30]=2)=[O:27])[CH:22]=[CH:23][CH:24]=1.CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.ClCCl>[CH3:36][O:35][C:33]1[CH:34]=[C:29]([NH:28][C:26](=[O:27])[CH2:25][C:21]2[CH:22]=[CH:23][CH:24]=[C:19]([NH:18][C:1]([C:4]3[C:5]([C:10]4[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=4[F:17])=[N:6][O:7][C:8]=3[CH3:9])=[O:3])[CH:20]=2)[CH:30]=[C:31]([O:39][CH3:40])[C:32]=1[O:37][CH3:38]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 187562503-(2,6-Difluorophenyl)-5-methylisoxazole-4-carboxylic acidHCID 187562602-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamide

Product 1

HCID 60083764N-(3,4,5-Trimethoxyphenyl)-3-(5-methyl-3-(2,6-difluoro-phenyl)isoxazol-4-oyl)aminophenyl AcetamideYield 53%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Carboxy-5-methyl-3-(2,6-difluorophenyl)isoxazole (0.120 g, 0.50 mmol), 2-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamide (0.174 g, 0.55 mmol), EDCI (0.161 g, 1.00 mmol), DMAP (0.012 g, 0.10 mmol), and dichloromethane (5 ml) were allowed to react for 16 h in a fashion similar to that for example 5. Column chromatography (silica gel, hexanes/ethyl acetate gradient) afforded the title compound (0.142 g, 53%).

Workup

  1. customto react for 16 h in a fashion similar to that for example 5

Sources & evidence

ORD record
ord-5fa21f89bd914bdea8af2bf39e21c609
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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