3,3,3-Trifluoropropane-1-sulfonyl chloride → HCID 86686193, compound

HRID 929526Notes

Reaction equation

[F:1][C:2]([F:10])([F:9])[CH2:3][CH2:4][S:5](Cl)(=[O:7])=[O:6].CS([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[O:23])[CH2:17][CH2:16]1)(=O)=O>>[F:1][C:2]([F:10])([F:9])[CH2:3][CH2:4][S:5]([N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:32])([F:33])[F:34])=[CH:27][CH:26]=2)=[O:23])[CH2:17][CH2:16]1)(=[O:7])=[O:6]

Participants

Reactant 2

HCID 27611773,3,3-Trifluoropropane-1-sulfonyl chloride

HCID 24899523HCID 24899523, compound

Product 1

HCID 86686193HCID 86686193, compoundYield 51%

Procedure

3,3,3-Trifluoropropylsulfonyl chloride (96 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 (55 mg, 0.123 mmol, 51% 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), 3.82 (d, J=Hz, 1H), 3.73 (m, 1H), 3.18 (t, J=12.4 Hz, 1H), 2.82 (m, 1H), 2.78 (t, J=Hz, 1H), 1.80 (t, J=9.6, 2H), 1.43 (m, 2H), 0.97 (s, 6H).

Sources & evidence

ORD record: ord-a4a01476158b40e386bb2e52dac01914
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296693B2

Reaction notes

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