3-Aminosalicylic acid → HCID 66799978, compound

HRID 589795Notes

Reaction equation

HRID 589795 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10](Cl)(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1.[NH2:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:19]([C:20]([OH:22])=[O:21])[C:18]=1[OH:26]>O.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:16][C:17]3[C:18]([OH:26])=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=[O:21])(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1

Participants

4

Reactant 2

HCID 684433-Aminosalicylic acidHCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride

Product 1

HCID 66799978HCID 66799978, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A solution of 5-chloro-3-methyl-benzothiophene-2-sulfonyl chloride (17 mg, 0.060 mmol) and 3-aminosalicylic acid (14 mg, 0.090 mmol) in 1200 μL of water/dioxane (1:6) 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 72% yield (17.2 mg). 1H NMR (500 MHz, DMSO-d6) δ ppm 2.48 (s, 3 H) 6.85 (t, J=7.92 Hz, 1 H) 7.46 (dd, J=7.69, 1.64 Hz, 1 H) 7.55 (dd, J=8.66, 2.05 Hz, 1 H) 7.63 (dd, J=7.92, 1.64 Hz, 1 H) 8.00 (dd, J=2.05, 0.47 Hz, 1 H) 8.04 (dd, J=8.66, 0.47 Hz, 1 H) 10.17 (br. 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-a989e8caea2847b395e4000d2baf39c3
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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