Triethylamine → HCID 22714015, compound

HRID 352191Notes

Reaction equation

HRID 352191 reaction equation
C(C1C(C2C=[C:14]([F:16])[CH:13]=[CH:12][C:11]=2Cl)=NOC=1Cl)(O)=O.[C:18](Cl)(=O)[C:19]([Cl:21])=[O:20].[NH2:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH:27]([CH2:31][NH:32][C:33](=[O:40])[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:26]1.C([N:43]([CH2:46][CH3:47])CC)C.C[C:49](C)=[O:50].[CH2:52]([Cl:54])Cl>ClCCl.CN(C=O)C>[Cl:21][C:19]1[O:20][N:43]=[C:46]([C:47]2[C:52]([Cl:54])=[CH:11][CH:12]=[CH:13][C:14]=2[F:16])[C:18]=1[C:49]([NH:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH:27]([CH2:31][NH:32][C:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:40])[CH2:26]1)=[O:50]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 22713868HCID 22713868, compoundHCID 131724454HCID 131724454, compound

Product 1

HCID 22714015HCID 22714015, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

In a fashion similar to that described for preparation 267, 4-carboxy-5-chloro-3-(2-chloro-5-fluorophenyl)isoxazole acid (0.22 g, 0.84 mmol), dichloromethane (2 ml), oxalyl chloride (0.15 ml, 1.68 mmol), DMF (0.01 ml), dichloromethane (5 ml), N-(3-Amino-cyclohexylmethyl)-benzamide (0.15 g, 0.65 mmol), and triethylamine (0.35 ml, 2.52 mmol) gave the title compound (0.29 g, 90%) after flash chromatography (silica gel, Acetone/CH2Cl2 gradient). Mass Spectrum (ES+) (m/z) 490.1 [M+1].

Sources & evidence

ORD record
ord-0481027a2f3247178a28ab4051e0192a
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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