Methanesulfonamide → HCID 58088342, compound

HRID 250288Notes

Reaction equation

HRID 250288 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[S:26][C:25]([C:27](O)=[O:28])=[CH:24][CH:23]=3)=[C:18]([CH3:30])[CH:17]=2)=[C:12]([CH:31]([CH3:33])[CH3:32])[O:11][N:10]=1.Cl.CN(C)CCCN=C=NCC.[CH3:46][S:47]([NH2:50])(=[O:49])=[O:48]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[S:26][C:25]([C:27]([NH:50][S:47]([CH3:46])(=[O:49])=[O:48])=[O:28])=[CH:24][CH:23]=3)=[C:18]([CH3:30])[CH:17]=2)=[C:12]([CH:31]([CH3:32])[CH3:33])[O:11][N:10]=1

Participants

5

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 672725595-{4-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-thiophene-2-carboxylic acid

Product 1

HCID 58088342HCID 58088342, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5-{4-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-2-methyl-phenyl}-thiophene-2-carboxylic acid (250 mg, 0.5 mmol), 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide hydrochloride (144 mg, 0.75 mmol), N,N′-dimethylamino pyridine (122 mg, 1.0 mmol) and methanesulfonamide (57 mg, 0.6 mmol) in dichloromethane (20 mL) is stirred at ambient temperature overnight. The reaction mixture is diluted with dichloromethane and washed with 1N HCl. The organic phase is concentrated under reduced pressure and purified by column chromatography (gradient: 0 to 20% EtOAc in hexanes with 0.1% AcOH) to give the title compound (160 mg, 55%). LC-ES/MS m/e 579 (M+1), 100%.

Workup

  1. washwashed with 1N HCl
  2. concentrationThe organic phase is concentrated under reduced pressure
  3. custompurified by column chromatography (gradient: 0 to 20% EtOAc in hexanes with 0.1% AcOH)

Sources & evidence

ORD record
ord-c7f045672a164b1fb1df35faa7efec9c
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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