2,2,2-Trifluoroethanesulfonyl chloride → HCID 56968121, compound

HRID 929525Notes

Reaction equation

HRID 929525 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][S:4](Cl)(=[O:6])=[O:5].CS([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[O:22])[CH2:16][CH2:15]1)(=O)=O>>[F:1][C:2]([F:9])([F:8])[CH2:3][S:4]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:26][CH:25]=2)=[O:22])[CH2:16][CH2:15]1)(=[O:6])=[O:5]

Participants

3

Reactant 2

HCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 24899523HCID 24899523, compound

Product 1

HCID 56968121HCID 56968121, compoundYield 46%

Procedure

2,2,2-trifluoroethylsulfonyl chloride (89 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 (48 mg, 0.111 mmol, 46% yield). 1H NMR (d6-DMSO, 300 Mhz): δ 8.81 (s, 1H), 7.56 (s, 4H), 6.41 (d, J=6.9 Hz, 1H), 4.51 (q, J=9.9 Hz, 2H), 3.58 (d, J=12 Hz, 1H), 3.58 (m, 1H), 3.02 (t, J=11.4 Hz, 2H), 1.92 (d, J=12.4 Hz, 2H), 1.45 (m, 2H).

Sources & evidence

ORD record
ord-f6f6127abb7d49d7acdee60cdba76285
Source dataset
uspto-grants-2016_03
Patent number
US09296693B2

Reaction notes

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