Methyl iodide → 5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-methylamide

HRID 2763

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([NH:12][S:13]([C:16]2[S:24][C:23]3[C:18](=[N:19][C:20]([Cl:25])=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])[C:8]1=[O:26])#[N:2].CI.[H-].[Na+].[CH3:34]COC(C)=O>CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:27]=[CH:28][CH:29]=1)[CH2:6][N:7]1[CH2:11][CH2:10][C@H:9]([N:12]([CH3:34])[S:13]([C:16]2[S:24][C:23]3[C:18](=[N:19][C:20]([Cl:25])=[CH:21][CH:22]=3)[CH:17]=2)(=[O:15])=[O:14])[C:8]1=[O:26])#[N:2]

Participants

Conditions

Temperature: 0 °C

Procedure

5-Chlorothieno[3,2-b]pyridine-2-sulfonic acid [1-(3-cyanobenzyl)-2-oxo-pyrrolidin-3-(S)-yl]-amide (0.25 g, 0.56 mmol) is dissolved in 6 mL of DMF and cooled to 0° C. To the solution is added methyl iodide (0.40 g, 2.82 mmol) and sodium hydride (25 mg of a 60% dispersion in mineral oil, 0.62 mmol). The reaction mixture is allowed to warm to room temperature and is stirred for 2 h. At this time, the solution is diluted with and EtOAc and the layers are separated. The organic layer is washed with 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl. The organic phase is then dried over MgSO4, filtered and concentrated to give the title compound (0.25 g, 0.54 mmol) as a solid.

Workup

temperatureto warm to room temperature
customthe layers are separated
washThe organic layer is washed with 1N HCl, H2O, saturated NaHCO3 solution and saturated NaCl
dry with materialThe organic phase is then dried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-e34502d7c6c04c4ba22048fd23ff4bf0
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05731315

Linked notes

Loading…