5-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride → HCID 56942777, compound

HRID 589801Notes

Reaction equation

HRID 589801 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.[O:16]1[C:20]([C:21]2[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=2)[NH2:24])=[CH:19][N:18]=[CH:17]1>O1CCOCC1.CO.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10]([NH:24][C:23]3[CH:25]=[CH:26][CH:27]=[C:21]([C:20]4[O:16][CH:17]=[N:18][CH:19]=4)[CH:22]=3)(=[O:12])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1

Participants

5

Reactant 2

HCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chlorideHCID 27392893-(1,3-Oxazol-5-yl)aniline

Product 1

HCID 56942777HCID 56942777, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution containing 5-chloro-3-methyl-benzothiophene-2-sulfonyl chloride (20 mg, 0.071 mmol) and 3-(1,3-oxazol-5-yl)-aniline (17 mg, 0.11 mmol) in aqueous dioxane (1 mL, 95:5 dioxane/water) was stirred at room temperature for 4 weeks. The reaction mixture was diluted with MeOH/water and the crude product was purified by reversed phase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, gradient: 0.1% TFA in water/MeCN over 6 minutes). The title compound was obtained in 63% yield (18 mg). 1H NMR (500 MHz, DMSO-d6) δ ppm 2.54 (s, 3 H) 7.09-7.16 (m, 1 H) 7.35 (t, J=7.93 Hz, 1 H) 7.45 (d, J=8.06 Hz, 1 H) 7.52 (t, J=1.83 Hz, 1 H) 7.56 (dd, J=8.79, 2.20 Hz, 1 H) 7.61 (s, 1 H) 8.00 (d, J=1.71 Hz, 1 H) 8.06 (d, J=8.30 Hz, 1 H) 8.43 (s, 1 H) 10.96 (s, 1 H). MS (ESI+) m/z 405 [M+H]+.

Workup

  1. customthe crude product was purified by reversed phase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, gradient: 0.1% TFA in water/MeCN over 6 minutes)

Sources & evidence

ORD record
ord-8ae3da731ca249fab74978fcae7eaad7
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

Loading…