Triethylamine → HCID 57664594, compound

HRID 1467868Notes

Reaction equation

[CH:1]1([N:4]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][CH:30]=1>CN(C=O)C>[CH:1]1([N:4]([CH:14]2[CH2:19][CH2:18][N:17]([CH2:28][C:29]3[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][CH:30]=3)[CH2:16][CH2:15]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

N-Cyclopropyl-N-piperidin-4-yl-benzenesulfonamide (100 mg, 0.36 mmol) was dissolved in DMF (2.5 mL) and triethylamine (75 μL, 54 mg, 0.54 mmol) added, followed by 1-bromomethyl-4-isopropylbenzene (83.5 mg, 0.39 mmol). The reaction mixture was stirred for 12 hours at 80° C. and then the solvent was evaporated. The residue was purified by flash chromatography to give 29 mg of the title compound 17 as a yellow oil. 1H NMR (CDCl3): δ 7.88-7.83 (m, 2H), 7.59-7.47 (m, 3H), 7.21-7.14 (m, 4H), 3.89-3.78 (m, 1H), 3.45 (s, 2H), 2.95-2.88 (m, 3H), 2.03-1.84 (m, 5H), 1.51-1.44 (m, m, 2H), 1.23 (d, 6H, J=7.01 Hz), 1.01-0.93 (m, 2H), 0.79-0.69 (m, 2H). LC: 100%. MS (EI): m/z 413 (M+H+).

Workup

customthe solvent was evaporated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-ad4a2778eae1489facaabb5c87bb8bb0
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000174B2

Reaction notes

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