Methyl Carbamate → N-[7-(4-piperidinyl)oxy-1-benzofuran-5-yl]-2-methoxy-5-methylbenzenesulfonamide

HRID 730551Notes

Reaction equation

HRID 730551 reaction equation
I[C:2]1[C:10]2OC=[CH:7][C:6]=2[CH:5]=[C:4]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=2OC)(=[O:13])=[O:12])[CH:3]=1.[C:24](=[O:28])(OC)N.S([O-])(=O)(=O)C.[OH:34][CH:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.[OH:41][C:42]1C2OC=CC=2C=C(S(NC2C=C(C)C=CC=2OC)(=O)=O)C=1>[Cu].COC1C=CC(C)=CC=1NS(C1C=C(OC2CCN(C(OC)=O)CC2)C2OC=CC=2C=1)(=O)=O>[NH:38]1[CH2:39][CH2:40][CH:35]([O:34][C:17]2[C:18]3[O:41][CH:42]=[CH:21][C:19]=3[CH:20]=[C:15]([NH:14][S:11]([C:4]3[CH:5]=[C:6]([CH3:7])[CH:10]=[CH:2][C:3]=3[O:28][CH3:24])(=[O:12])=[O:13])[CH:16]=2)[CH2:36][CH2:37]1

Participants

8

Reactant 5

HCID 11722Methyl CarbamateHCID 79341Piperidin-4-olHCID 85257MethanesulfonateHCID 668925067-Iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamideHCID 688571197-hydroxy-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide

Product 1

HCID 11983287N-[7-(4-piperidinyl)oxy-1-benzofuran-5-yl]-2-methoxy-5-methylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 68855386Methyl 4-[(5-{[(2-methoxy-5-methylphenyl)amino]sulfonyl}-1-benzofuran-7-yl)oxy]piperidine-1-carboxylateSolvent

Procedure

Hydrolysis of 7-iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide in alkaline solution using copper as catalyst results in 7-hydroxy-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide. Reaction with a methyl carbamate protected mesylate of 4-hydroxypiperidine, results in methyl 4-[(5-{[(2-methoxy-5-methylphenyl)amino]sulfonyl}-1-benzofuran-7-yl)oxy]piperidine-1-carboxylate, which is hydrolysed in alkaline solution giving the title compound.

Sources & evidence

ORD record
ord-99e6b72eb0594a5892ca4dbe0334a43e
Source dataset
uspto-grants-2009_09
Patent number
US07582767B2

Reaction notes

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