Triethylamine → N-(3,4,5-Trimethoxyphenyl)-3-(5-methyl-3-(2-fluoro-4-bromo-phenyl)isoxazol-4-oyl)aminophenyl Acetamide

HRID 434051Notes

Reaction equation

HRID 434051 reaction equation
[C:1]([C:4]1[C:5]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=2[F:17])=[N:6][O:7][C:8]=1[CH3:9])([OH:3])=O.C(Cl)(=O)C(Cl)=O.[NH2:24][C:25]1[CH:26]=[C:27]([CH2:31][C:32]([NH:34][C:35]2[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=2)=[O:33])[CH:28]=[CH:29][CH:30]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl.CN(C)C=O>[CH3:42][O:41][C:39]1[CH:40]=[C:35]([NH:34][C:32](=[O:33])[CH2:31][C:27]2[CH:28]=[CH:29][CH:30]=[C:25]([NH:24][C:1]([C:4]3[C:5]([C:10]4[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=4[F:17])=[N:6][O:7][C:8]=3[CH3:9])=[O:3])[CH:26]=2)[CH:36]=[C:37]([O:45][CH3:46])[C:38]=1[O:43][CH3:44]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 187562602-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamideHCID 187562854-Carboxy-5-methyl-3-(2-fluoro-4-bromophenyl)isoxazole

Product 1

HCID 60083763N-(3,4,5-Trimethoxyphenyl)-3-(5-methyl-3-(2-fluoro-4-bromo-phenyl)isoxazol-4-oyl)aminophenyl AcetamideYield 66%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

In a fashion similar to that described for preparation 35, 4-carboxy-5-methyl-3-(2-fluoro-4-bromophenyl)isoxazole (119 mg, 0.40 mmol), oxalyl chloride (0.070 ml, 0.80 mmol), dimethylformamide (0.010 ml), dichloromethane (5 ml), 2-(3-aminophenyl)-N-(3,4,5-trimethoxyphenyl)acetamide (110 mg, 0.35 mmol), triethylamine (0.111 ml, 0.80 mmol), DMAP (5 mg), dimethylformamide (1 ml), dichloromethane (5 ml) gave the title compound (138 mg, 66%) after column chromatography (silica gel, hexanes/ethyl acetate gradient).

Sources & evidence

ORD record
ord-a989a6e051da4432a223da94deb17734
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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