Triethylamine → HCID 57664572, compound

HRID 1467871Notes

Reaction equation

[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([C:41]([F:44])([F:43])[F:42])[CH:34]=1>CN(C=O)C>[CH:1]1([N:4]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([C:41]([F:42])([F:43])[F:44])[CH:34]=3)[CH2:20][CH2:19]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

N-Cyclopropyl-N-piperidin-4-yl-3-trifluoromethylbenzenesulfonamide (200 mg, 0.57 mmol) was dissolved in DMF (4 mL) and triethylamine (200 μL, 1.43 mmol) added, followed by 4-bromomethyl-1-methoxy-2-trifluoromethyl-benzene (154 mg, 0.57 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 244 mg of the title compound 18 as a yellow solid. 1H NMR (CDCl3): δ 8.14-8.11 (m, 1H), 8.07-8.03 (m, 1H), 7.86-7.80 (m, 1H), 7.70-7.64 (m, 1H), 7.50-7.47 (m, 1H), 7.42-7.37 (m, 1H), 6.96-6.91 (m, 1H), 3.93-3.79 (m, 4H), 3.42 (s, 2H), 2.91-2.80 (m, 2H), 2.03-1.85 (m, m, 5H), 1.53-1.44 (m, 2H), 1.02-0.96 (m, 2H), 0.83-0.76 (m, 2H). LC: 100%. MS (EI): m/z 537 (M+H+).

Workup

customthe solvent was evaporated
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-5d8e4a735a9d4d538355dd5a83c6e45b
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000174B2

Reaction notes

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