1,2-Dichloroethane → HCID 11576363, compound

HRID 729294Notes

Reaction equation

[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18]([C:20]([OH:22])=O)=[CH:17][C:16]=3[CH:23]=2)=[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[S:6]1(=[O:31])=[O:30])[CH2:2][CH2:3][CH3:4].[CH3:32][NH:33][CH3:34].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C1COCC1.CN(C=O)C.CCOC(C)=O>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:11][C:12]2[CH:13]=[CH:14][C:15]3[O:19][C:18]([C:20]([N:33]([CH3:34])[CH3:32])=[O:22])=[CH:17][C:16]=3[CH:23]=2)=[C:7]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[S:6]1(=[O:31])=[O:30])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 5-[(2-Butyl-1,1-dioxido-3-oxo-5-phenyl-2,3-dihydroisothiazol-4-yl)amino]-1-benzofuran-2-carboxylic acid (example 51) (0.100 g, 0.227 mmol), dimethylamine in THF (2M, 0.321 ml), EDC (0.132 g, 0.681 mmol), HOBt (0.065 g, 0.249 mmol) and TEA (0.090 ml, 0.681 mmol) in DMF (2 ml) was heated at 70° C. for 18 h. EtOAc was added and the mixture was washed with brine, evaporated and the residue was purified by flash chromatography (Horizons Biotage) using 50-65% EtOAc in hexane as eluent to give the title compound (0.054 g, 51%); 1H NMR (500 MHz CDCl3); δ 7.18 (dd, 1H), 7.14-7.10 (m, 3H), 7.08-7.02 (m, 2H), 6.99 (s, 1H), 6.91 (d, 1H), 6.84 (dd, 1H), 3.81 (t, 2H), 3.30 (bs, 3H), 3.14 (bs, 3H), 1.94-1.86 (m, 2H), 1.56-1.46 (m, 2H), 1.02 (t, 3H); 13C NMR (125 MHz CDCl3): δ 161.0, 159.5, 152.1, 151.0, 132.1, 131.4, 129.5, 129.5, 128.3, 127.1, 124.9, 121.6, 115.9, 111.9, 111.4, 111.2, 40.5, 30.5, 20.3, 13.8.; Mass Spectrum M+H+ 468.

Workup

washthe mixture was washed with brine
customevaporated
customthe residue was purified by flash chromatography (Horizons Biotage)

Sources & evidence

ORD record: ord-65380e8404b14f9580e21a725936b89c
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582629B2

Reaction notes

Loading…