Pyridine → HCID 86689196, compound

HRID 589790Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10]CC)=[O:9])=[C:5]([CH3:7])[N:6]=1.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([S:22](Cl)(=[O:24])=[O:23])=[C:19]([CH3:26])[C:18]=2[CH:27]=1.N1C=CC=CC=1.[OH-].[Na+].C(O)(C(F)(F)F)=O>CC#N.O.CO.CS(C)=O>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([S:22]([NH:1][C:2]3[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=3)(=[O:24])=[O:23])=[C:19]([CH3:26])[C:18]=2[CH:27]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of ethyl 2-amino-4-methylthiazole-5-carboxylate (9.3 mg, 0.050 mmol), 5-chloro-3-methyl-benzothiophene-2-sulfonyl chloride (14 mg, 0.050 mmol) and pyridine (8 μL, 0.100 mmol) in MeCN (400 μL) was heated at 60° C. for 7 days. The solvent was removed and the residue redissolved in 1 M NaOH (300 μL, 0.300 mmol) and then heated at 60° C. over night. The crude product was diluted with water/MeOH/DMSO and acidified by addition of TFA. The 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 24% yield (4.9 mg). 1H NMR (500 MHz, MeOH-d4) δ ppm 2.47 (s, 3 H) 2.65 (s, 3H) 7.47 (dd, J=8.67, 2.08 Hz, 1 H) 7.88 (dd, J=8.67, 0.51 Hz, 1 H) 7.89 (dd, J=2.08, 0.51 Hz, 1 H). MS (ESI+) m/z 403 [M+H]+.

Workup

customThe solvent was removed
temperatureheated at 60° C. over night
customThe 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-35c1684e2a2946ebb44fa1d7c036360c
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233946B2

Reaction notes

Loading…