Methanesulfonamide → HCID 72613065, compound

HRID 2181126Notes

Reaction equation

CC1(C)[O:6][C:5](=[CH:7][C:8]([N:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([F:21])[CH:15]=2)[O:11][CH3:12])=[O:9])[C:4](=O)[O:3]1.[CH3:24][S:25]([NH2:28])(=[O:27])=[O:26]>>[F:21][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[CH3:20])[CH2:13][N:10]([O:11][CH3:12])[C:8](=[O:9])[CH:7]=[C:5]([OH:6])[C:4]([NH:28][S:25]([CH3:24])(=[O:27])=[O:26])=[O:3]

Participants

Reactant 2

HCID 72879Methanesulfonamide

HCID 73855569HCID 73855569, compound

Product 1

HCID 72613065HCID 72613065, compoundYield 68%

Procedure

Reaction of 2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(3-fluoro-4-methyl-benzyl)-N-methoxy-acetamide (0.135 g, 0.418 mmol) with methanesulfonamide (0.042 g, 0.44 mmol) as described in the preparation of compound 22 gave 0.102 g (68% yield) of the title amide as a white solid. 1H NMR (400 MHz, DMSO) δ: mixture of rotamers: 2.2 (3H, s, CH3), 2.87 and 2.88 (3H, 2 S, SO2CH3), 3.63 and 3.67 (3H, 2 s, OCH3), 4.73 and 4.78 (2H, 2 s, NCH2), 6.14 and 6.16 (1H, 2 s, CH), 7.04-7.27 (3H, m, aromatics). HRMS (ESI/neg) calculated for C14H16FN2O6S: [M−H]−: 359.071312; found: 359.071347.

Sources & evidence

ORD record: ord-be4174bc4987406183d9a26bac0de350
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890942B2

Reaction notes

Loading…