Triethylamine → HCID 86670442, compound

HRID 1972693Notes

Reaction equation

[C:1]([C@@H:4]1[NH:9][CH2:8][CH2:7][N:6]([S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:12])=[O:11])[CH2:5]1)#[C:2][CH3:3].Cl[C:19]1[N:24]=[CH:23][C:22]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][N:20]=1.C(N(CC)CC)C>O1CCOCC1>[F:29][C:26]([F:27])([F:28])[C:25]([C:22]1[CH:23]=[N:24][C:19]([N:9]2[CH2:8][CH2:7][N:6]([S:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)(=[O:12])=[O:11])[CH2:5][C@@H:4]2[C:1]#[C:2][CH3:3])=[N:20][CH:21]=1)([OH:34])[C:30]([F:33])([F:32])[F:31].[F:29][C:26]([F:27])([F:28])[C:25]([C:22]1[CH:23]=[N:24][C:19]([N:9]2[CH2:8][CH2:7][N:6]([S:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)(=[O:12])=[O:11])[CH2:5][C@H:4]2[C:1]#[C:2][CH3:3])=[N:20][CH:21]=1)([OH:34])[C:30]([F:33])([F:32])[F:31]

Participants

Conditions

Temperature: 100 °C

Procedure

In a 50-mL sealed vial, a mixture of (S)-3-(prop-1-yn-1-yl)-1-(thiophen-2-ylsulfonyl)piperazine (40 mg, 0.148 mmol), 2-(2-chloropyrimidin-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-ol (41.5 mg, 0.148 mmol), and triethylamine (30.9 μl, 0.222 mmol) in dioxane was heated to 100° C. for 16 h. Afterwards, the mixture was concentrated and the crude material was purified via column chromatography (about 40 g silica gel, 0% to 10% MeOH in CH2Cl2) to give the racemate of 1,1,1,3,3,3-hexafluoro-2-(2-((2S)-2-(1-propyn-1-yl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)-5-pyrimidinyl)-2-propanol (18 mg) and 1,1,1,3,3,3-hexafluoro-2-(2-((2R)-2-(1-propyn-1-yl)-4-(2-thiophenylsulfonyl)-1-piperazinyl)-5-pyrimidinyl)-2-propanol (18 mg).

Workup

customIn a 50-mL sealed vial
concentrationAfterwards, the mixture was concentrated
customthe crude material was purified via column chromatography (about 40 g silica gel, 0% to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-2192ccca44454974a9b66c319d7b37aa
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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