Cyclopropanesulfonyl chloride → HCID 56968120, compound

HRID 929527Notes

Reaction equation

[CH:1]1([S:4](Cl)(=[O:6])=[O:5])[CH2:3][CH2:2]1.CS([N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)=[O:20])[CH2:14][CH2:13]1)(=O)=O>>[CH:1]1([S:4]([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:29])([F:30])[F:31])=[CH:24][CH:23]=3)=[O:20])[CH2:14][CH2:13]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

Reactant 2

HCID 2760919Cyclopropanesulfonyl chloride

HCID 24899523HCID 24899523, compound

Product 1

HCID 56968120HCID 56968120, compoundYield 54.1%

Procedure

Cyclopropylsulfonyl chloride (75 mg, 0.536 mmol) was reacted with ITU (70 mg, 0.268 mmol) as the same manner as the synthesis of 1-(1-(methylsulfonyl)piperidin-4-yl)-3-(4-(trifluoromethyl)phenyl)urea yielding the final product (53 mg, 0.145 mmol, 54.1% yield). 1H NMR (d6-DMSO, 300 Mhz): δ 8.20 (s, 1H), 7.26 (d, J=6.9 Hz, 2H), 7.07 (d, J=7.5 Hz, 2H), 6.14 (d, J=7.8 Hz, 1H), 3.59 (m, 1H), 3.52 (d, J=12.8 Hz, 2H), 2.98 (t, J=11.4 Hz, 2H), 2.79 (m, 1H), 2.57 (m, 1H), 1.90 (d, J=12.3 Hz, 2H), 1.42 (m, 2H), 1.15 (d, J=6.6 Hz, 6H), 0.95 (m, 4H).

Sources & evidence

ORD record: ord-b26cccf4edaf444e97ce23e13c9a75e6
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296693B2

Reaction notes

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