Methanesulfonyl chloride → HCID 86608328, compound

HRID 2233981Notes

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][CH2:7][CH2:8][O:9][C:10]1[N:15]=[C:14]([C:16]([NH:18][O:19][CH3:20])=[O:17])[CH:13]=[C:12]([N:21]2[CH2:26][CH2:25][CH:24]([NH:27][C:28]([C:30]3[NH:31][C:32]([CH3:37])=[C:33]([Cl:36])[C:34]=3[Cl:35])=[O:29])[CH2:23][CH2:22]2)[N:11]=1>CN(C=O)C>[Cl:35][C:34]1[C:33]([Cl:36])=[C:32]([CH3:37])[NH:31][C:30]=1[C:28]([NH:27][CH:24]1[CH2:23][CH2:22][N:21]([C:12]2[N:11]=[C:10]([O:9][CH2:8][CH2:7][NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[N:15]=[C:14]([C:16]([NH:18][O:19][CH3:20])=[O:17])[CH:13]=2)[CH2:26][CH2:25]1)=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

Methane sulfonyl chloride (0.032 ml, 0.412 mmol) was added dropwise to a solution of 2-(2-aminoethoxy)-6-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-N-methoxypyrimidine-4-carboxamide (Example 319, 0.20 g, 0.412 mmol), TEA (0.11 ml, 0.824 mmol) and DMF (3 ml) at 0° C. The reaction was stirred for 15 minutes at 0° C. then quenched with water. The aqueous phase was extracted with EtOAc, washed with saturated sodium bicarbonate solution, water and brine. It was dried over magnesium sulfate and concentrated to give brown solid, which was purified by reverse phase HPLC (30% to 35% acetonitrile in water, 0.1% TFA) affording the title compound (70 mg).

Workup

customthen quenched with water
extractionThe aqueous phase was extracted with EtOAc
washwashed with saturated sodium bicarbonate solution, water and brine
dry with materialIt was dried over magnesium sulfate
concentrationconcentrated
customto give brown solid, which
customwas purified by reverse phase HPLC (30% to 35% acetonitrile in water, 0.1% TFA)

Sources & evidence

ORD record: ord-54dc5dacab23492487734cd377416ef9
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709503B2

Reaction notes

Loading…