5-Aminosalicylic Acid → HCID 66800045, compound

HRID 589799Notes

Reaction equation

HRID 589799 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]([S:10](Cl)(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1.[NH2:16][C:17]1[CH:25]=[C:21]([C:22]([OH:24])=[O:23])[C:20]([OH:26])=[CH:19][CH:18]=1>O1CCOCC1>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[S:6][C:7]([S:10]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([OH:26])=[C:21]([CH:25]=3)[C:22]([OH:24])=[O:23])(=[O:12])=[O:11])=[C:8]([CH3:9])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 40755-Aminosalicylic AcidHCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride

Product 1

HCID 66800045HCID 66800045, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-chloro-3-methyl-benzo[b]thiophene-2-sulfonyl chloride (22 mg, 0.075 mmol) and 5-aminosalicylic acid (17 mg, 0.112 mmol) in aqueous dioxane (800 μL, 4:1 dioxane/water) was shaken at 35° C. for 5 days. The product was purified by reversed phase chromatography (ACE C8, 4 μm, 21×50 mm, flow 25 ml/min, gradient: 0.1% TFA in water/MeCN over 6 minutes). The title compound was obtained in 79% yield (23.6 mg). 1H NMR (500 MHz, DMSO-d6) δ ppm 2.41-2.43 (m, 3 H) 6.87 (d, J=8.79 Hz, 1 H) 7.20-7.25 (m, 1 H) 7.53 (dd, J=2.93, 1.46 Hz, 1 H) 7.56 (dd, J=8.79, 1.95 Hz, 1 H) 8.00 (d, J=1.95 Hz, 1 H) 8.06 (d, J=8.79 Hz, 1 H) 10.45 (s, 1 H). MS (ESI+) m/z 398 [M+H]+.

Workup

  1. customThe product was purified by reversed phase chromatography (ACE C8, 4 μm, 21×50 mm, flow 25 ml/min, gradient: 0.1% TFA in water/MeCN over 6 minutes)

Sources & evidence

ORD record
ord-3c14f12f6d3e4045b9ada9cb21ea24b6
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

Loading…