Cyclopropanesulfonyl chloride → HCID 56968120, compound

HRID 929523Notes

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 68%

Procedure

Cyclopropylsulfonyl chloride (68.5 mg, 0.487 mmol) was reacted with PTU (70 mg, 0.244 mmol) as the same manner as the synthesis of 1-(1-(methylsulfonyl)piperidin-4-yl)-3-(4-(trifluoromethyl)phenyl)urea yielding the final product (65 mg, 0.166 mmol, 68% yield). 1H NMR (d6-DMSO, 300 Mhz): δ 8.78 (s, 1H), 7.57 (s, 4H), 6.38 (d, J=7.5 Hz, 1H), 4.19 (d, J=Hz, 1H), 3.52 (d, J=12.3 Hz, 2H), 2.99 (t, J=11.4 Hz, 2H), 2.58 (m, 1H), 1.91 (d, J=12.6 Hz, 2H), 1.46 (m, 2H), 0.96 (m, 4H).

Sources & evidence

ORD record: ord-36a64d8f7a89401e813f2e520fffdf62
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296693B2

Reaction notes

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