Dichloromethane → N-(3,4,5-Trimethoxyphenyl)-3-(5-hexyl-3-(2-chloro-6-fluoro-phenyl)isoxazol-4-oyl)aminophenyl Acetamide

HRID 434042Notes

Reaction equation

HRID 434042 reaction equation
[C:1]([C:4]1[C:5]([C:15]2[C:20](F)=[CH:19][CH:18]=[CH:17][C:16]=2[F:22])=[N:6][O:7][C:8]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])([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.C(Cl)[Cl:58]>CN(C1C=CN=CC=1)C>[CH3:45][O:44][C:36]1[CH:35]=[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:16]([F:22])=[CH:17][CH:18]=[CH:19][C:20]=4[Cl:58])=[N:6][O:7][C:8]=3[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:3])[CH:25]=2)[CH:39]=[C:38]([O:40][CH3:41])[C:37]=1[O:42][CH3:43]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 187562602-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamideHCID 187562704-Carboxy-5-hexyl-3-(2,6-difluorophenyl)isoxazole

Product 1

HCID 60083760N-(3,4,5-Trimethoxyphenyl)-3-(5-hexyl-3-(2-chloro-6-fluoro-phenyl)isoxazol-4-oyl)aminophenyl AcetamideYield 65%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-Carboxy-5-hexyl-3-(2,6-difluorophenyl)isoxazole (150 mg, 0.46 mmol), 2-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamide (160 mg, 0.51 mmol), EDCI (150 mg, 0.78 mmol), DMAP (12 mg, 0.10 mmol) were reacted in CH2Cl2 (5 ml) for 19 h then applied to a silica gel column. Elution with hexanes/EtOAc (gradient) gave the title compound (185 mg, 65%).

Workup

  1. washElution with hexanes/EtOAc (gradient)

Sources & evidence

ORD record
ord-0c23cbdf6bb343ec81f702546cce21aa
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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