Water → 3-Nitro-4-(1-(tetrahydro-2h-pyran-4-yl)piperidin-4-ylamino)benzenesulfonamide

HRID 2045012Notes

Reaction equation

[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][CH:10]([NH2:13])[CH2:9][CH2:8]2)[CH2:3][CH2:2]1.O.C(N(CC)CC)C.Cl[C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][C:24]=1[N+:33]([O-:35])=[O:34]>O1CCOCC1>[N+:33]([C:24]1[CH:25]=[C:26]([S:29]([NH2:32])(=[O:30])=[O:31])[CH:27]=[CH:28][C:23]=1[NH:13][CH:10]1[CH2:11][CH2:12][N:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH2:8][CH2:9]1)([O-:35])=[O:34]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of EXAMPLE 173B (22.12 g), water (43 mL), and triethylamine (43.6 mL) in 1,4-dioxane (300 mL) was stirred at room temperature until EXAMPLE 173B completely dissolved. The solution was then treated with 4-chloro-3-nitrobenzenesulfonamide, heated at 90° C. for 16 hours, cooled and concentrated. 10% methanol in dichloromethane was added, and the solution was stirred vigorously at room temperature until a fine suspension existed and the mixture was filtered.

Workup

dissolutioncompletely dissolved
temperaturecooled
concentrationconcentrated
addition10% methanol in dichloromethane was added
filtrationthe mixture was filtered

Sources & evidence

ORD record: ord-72b145c9bf5e4a9ca2a3592951931f0a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586754B2

Reaction notes

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