Methanesulfonyl chloride → HCID 59985220, compound

HRID 23654Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[C:7]2[N:8]([CH3:24])[CH:9]=[C:10]([C:13]([NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)=[O:14])[C:11](=[O:12])[C:6]=2[S:5][C:4]=1[CH2:25][N:26]([CH2:28][C@@H:29]([OH:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1)[CH3:27].C(N(C(C)C)CC)(C)C.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>C(Cl)Cl>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][NH:15][C:13]([C:10]2[C:11](=[O:12])[C:6]3[S:5][C:4]([CH2:25][N:26]([CH2:28][C@@H:29]([OH:36])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=4)[CH3:27])=[C:3]([CH2:2][NH:1][S:47]([CH3:46])(=[O:49])=[O:48])[C:7]=3[N:8]([CH3:24])[CH:9]=2)=[O:14])=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.), stirred solution of 96 mg of 3-(aminomethyl)-N-(4-chlorobenzyl)-2-{[[(2R)-2-hydroxy-2-pyridin-2-ylethyl](methyl)amino]methyl}-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide and 40 μL of diisopropylethylamine in 2 mL of CH2Cl2 is added 15 μL of methanesulfonyl chloride. The solution is stirred at 0° C. for 20 min, then quenched with dil. HCl and aqueous NaHCO3 to pH 7.0. The mixture is extracted three times with CHCl3, and the combined extracts dried (Na2SO4) and concentrated under reduced pressure. Flash chromatography of the residue on silica using 3-4% MeOH in CH2Cl2 furnishes 114 mg of the title compound as a white foam. Recrystallization from EtOAc provides white crystals.

Workup

customquenched with dil. HCl and aqueous NaHCO3 to pH 7.0
extractionThe mixture is extracted three times with CHCl3
dry with materialthe combined extracts dried (Na2SO4)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e2b71ea804d44ae4b08706caee6975d1
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06852731B2

Reaction notes

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