Ethanesulfonyl chloride → HCID 56971641, compound

HRID 929520Notes

Reaction equation

[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].CS([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)=[O:19])[CH2:13][CH2:12]1)(=O)=O>>[CH2:1]([S:3]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:23][CH:22]=2)=[O:19])[CH2:13][CH2:12]1)(=[O:5])=[O:4])[CH3:2]

Participants

Reactant 2

HCID 11667Ethanesulfonyl chloride

HCID 24899523HCID 24899523, compound

Product 1

HCID 56971641HCID 56971641, compoundYield 43%

Procedure

Ethylsulfonyl chloride (63 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 (40 mg, 0.105 mmol, 43% yield). 1H NMR (d6-DMSO, 300 Mhz): δ 8.77 (s, 1H), 7.57 (s, 4H), 6.38 (d, J=7.2 Hz, 1H), 3.63 (m, 1H), 3.52 (d, J=12.3 Hz, 2H), 3.05 (m, 5H), 1.89 (d, J=10 Hz, 2H), 1.47 (m, 2H), 1.22 (t, J=4.8 Hz, 3H).

Sources & evidence

ORD record: ord-c9c0158303624d5999ddb115bf683472
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296693B2

Reaction notes

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