2-cyclopentyl-6-hydroxybenzo[d]isothiazol-3(2H)-one → 3'-((2-Cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylic acid

HRID 404967Notes

Reaction equation

HRID 404967 reaction equation
[CH:1]1([N:6]2[C:10](=[O:11])[C:9]3[CH:12]=[CH:13][C:14]([OH:16])=[CH:15][C:8]=3[S:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:18][C:19]1[CH:20]=[C:21]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([O:33]C)=[O:32])=[CH:27][CH:26]=2)[CH:22]=[CH:23][CH:24]=1>>[CH:1]1([N:6]2[C:10](=[O:11])[C:9]3[CH:12]=[CH:13][C:14]([O:16][CH2:18][C:19]4[CH:20]=[C:21]([C:25]5[CH:30]=[CH:29][C:28]([C:31]([OH:33])=[O:32])=[CH:27][CH:26]=5)[CH:22]=[CH:23][CH:24]=4)=[CH:15][C:8]=3[S:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

3

Reactant 2

HCID 250674612-cyclopentyl-6-hydroxybenzo[d]isothiazol-3(2H)-oneHCID 66799590Methyl 3'-(bromomethyl)-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 533906793'-((2-Cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylic acidYield 35%

Procedure

2-Cyclopentyl-6-hydroxybenzo[d]isothiazol-3(2H)-one (0.094 g, 0.4 mmol) and methyl 3′-(bromomethyl)biphenyl-4-carboxylate (0.146 g, 0.48 mmol) were processed according to the general procedure described for Example 19 to afford 3′-((2-cyclopentyl-3-oxo-2,3-dihydrobenzo[d]isothiazol-6-yloxy)methyl)biphenyl-4-carboxylic acid as a colorless solid in 35% yield over 2 steps (0.053 g, after HPLC purification). 1H NMR (400 MHz, DMSO-d6): δ 7.99 (d, 2H, J=8.6 Hz), 7.83-7.79 (m, 5H), 7.70-7.69 (m, 1H), 7.51-7.42 (m, 2H), 7.45 (d, 1H, J=8.5 Hz), 5.34 (s, 2H), 4.49-4.47 (m, 1H), 1.86-1.76 (m, 2H), 1.75-1.57 (m, 6H). HRMS (ESI) calcd for C26H23NO4S [M+H]+: 446.1420. Found: 446.1420.

Sources & evidence

ORD record
ord-87d36bf08bd945debfe2d71d30cb604a
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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