Methanesulfonyl chloride → N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide

HRID 2390839Notes

Reaction equation

[NH2:1][C:2]1[CH:31]=[CH:30][C:5]([C:6]([N:8]([C:10]2[CH:15]=[C:14]([C:16]3[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:13]=[C:12]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:11]=2[O:28][CH3:29])[CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1.CCOC(C)=O>[C:24]([C:12]1[C:11]([O:28][CH3:29])=[C:10]([N:8]([CH3:9])[C:6](=[O:7])[C:5]2[CH:30]=[CH:31][C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])=[CH:3][CH:4]=2)[CH:15]=[C:14]([C:16]2[C:17]([O:22][CH3:23])=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:13]=1)([CH3:25])([CH3:26])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

step 3—To a solution of 140 (0.15 g, 0.36 mmol) in pyridine (3 mL) cooled to 0° C. was added methanesulfonyl chloride (0.053 g, 0.46 mmol) and the resulting solution stirred at 0° C. for 2 h, followed by 2 h at RT. The reaction mixture was diluted with EtOAc, washed sequentially with aqueous CuSO4 and 2N HCl, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient to afford 0.17 g (97%) of N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-methanesulfonylamino-N-methylbenzamide (142) as a white foam (0.17 g, 94%

Workup

waitfollowed by 2 h at RT
washwashed sequentially with aqueous CuSO4 and 2N HCl
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by SiO2 chromatography
washeluting with an EtOAc/hexane gradient

Sources & evidence

ORD record: ord-67ec89a0183148e6be83f0d73097f29d
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273773B2

Reaction notes

Loading…