Methanesulfonyl chloride → HCID 59259093, compound

HRID 641841Notes

Reaction equation

[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([CH2:12]O)=[CH:10][CH:9]=[CH:8][N:7]=1.CCN(C(C)C)C(C)C.S(Cl)(C)(=O)=O.[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]#[CH:38])=[CH:31][C:30]=1[C:39]([C:41]1[CH:46]=[CH:45][C:44]([CH:47]([CH3:49])[CH3:48])=[CH:43][CH:42]=1)=[O:40]>O1CCOCC1>[CH:47]([C:44]1[CH:43]=[CH:42][C:41]([C:39]([C:30]2[CH:31]=[C:32]([O:35][CH2:36][C:37]#[CH:38])[CH:33]=[CH:34][C:29]=2[NH:28][CH2:12][C:11]2[C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[N:7][CH:8]=[CH:9][CH:10]=2)=[O:40])=[CH:46][CH:45]=1)([CH3:49])[CH3:48]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 400 mg (2.18 mmol) [2-(2-methoxy-ethoxy)-pyridin-3-yl]-methanol in 4 ml dioxane at r.t. is added 1.12 ml (6.55 mmol) Hünig's base followed by 170 μl (2.18 mmol) mesyl chloride and the mixture is stirred for 5 min. 641 mg (2.18 mmol) (2-amino-5-propargyloxy-phenyl)-(4-isopropyl-phenyl)-methanone is added to this mixture with the addition of 1 ml of dioxane. The reaction mixture is then heated to 100° C. and stirred overnight. The mixture is partitioned between ether/water and the organic layer is washed with brine, dried with Na2SO4, filtered and evaporated. Flash-chromatography (ethyl acetate/ether 1:1) yields a yellow oil

Workup

stirringstirred overnight
customThe mixture is partitioned between ether/water
washthe organic layer is washed with brine
dry with materialdried with Na2SO4
filtrationfiltered
customevaporated
customFlash-chromatography (ethyl acetate/ether 1:1) yields a yellow oil

Sources & evidence

ORD record: ord-26595e5e427149e4909ef964a34f7fa9
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07696216B2

Reaction notes

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