Triethylamine → HCID 66582784, compound

HRID 1972504Notes

Reaction equation

[CH2:1]([C@H:8]1[CH2:13][NH:12][CH2:11][CH2:10][N:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Br:34][C:35]1[S:39][C:38]([S:40](Cl)(=[O:42])=[O:41])=[CH:37][CH:36]=1>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:13][N:12]([S:40]([C:38]2[S:39][C:35]([Br:34])=[CH:36][CH:37]=2)(=[O:42])=[O:41])[CH2:11][CH2:10][N:9]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:26])([CH3:25])[C:21]([F:24])([F:23])[F:22])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The 2-(4-((2S)-2-benzyl-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (147 mg, 0.404 mmol) was dissolved in CH2Cl2 (10 mL) was cooled to 0° C. To this solution was added triethylamine (124 μL, 0.889 mmol) followed by 5-bromothiophene-2-sulfonyl chloride (127 mg, 0.485 mmol, Sigma-Aldrich, St. Louis, Mo.). The mixture was allowed to slowly warm to room temperature and stirred for 2 h. The mixture was concentrated and absorbed onto silica gel. The crude material was purified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2) to give 2-(4-((2S)-2-benzyl-4-((5-bromo-2-thiophenyl)sulfonyl)-1-piperazinyl)phenyl)-1,1,1-trifluoro-2-propanol (105 mg).

Workup

temperatureto slowly warm to room temperature
concentrationThe mixture was concentrated
customabsorbed onto silica gel
customThe crude material was purified via column chromatography (40 g silica gel, 0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-f38af461cb07471d8f7f1019f09e670f
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

Loading…