Triethylamine → 2-(2-((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol

HRID 1972505Notes

Reaction equation

Cl.[F:2][C:3]([F:21])([F:20])[C:4]([C:7]1[CH:8]=[N:9][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@@H:14]2[CH3:19])=[N:11][CH:12]=1)([OH:6])[CH3:5].C(N(CC)CC)C.[N+:29]([C:32]1[S:36][C:35]([S:37](Cl)(=[O:39])=[O:38])=[CH:34][CH:33]=1)([O-:31])=[O:30]>C(Cl)Cl>[N+:29]([C:32]1[S:36][C:35]([S:37]([N:16]2[CH2:17][CH2:18][N:13]([C:10]3[N:11]=[CH:12][C:7]([C:4]([OH:6])([CH3:5])[C:3]([F:2])([F:20])[F:21])=[CH:8][N:9]=3)[C@@H:14]([CH3:19])[CH2:15]2)(=[O:39])=[O:38])=[CH:34][CH:33]=1)([O-:31])=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

The 1,1,1-trifluoro-2-(2-((2S)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-2-propanol hydrochloride (95 mg, 0.291 mmol) was dissolved in CH2Cl2 (15 mL) was chilled to 0° C. To this solution was added triethylamine (101 μL, 0.727 mmol) followed by 5-nitrothiophene-2-sulfonyl chloride (66.2 mg, 0.291 mmol, Enamine Building Blocks, Kiev, Ukraine). The mixture was warmed slowly to room temperature and stirred for 2 h. Afterwards, the mixture was concentrated onto silica gel and then purified via column chromatography (24 g silica gel, 0 to 10% MeOH in CH2Cl2) to give racemic 2-(2-((2S)-4-((5-nitro-2-thiophenyl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1-trifluoro-2-propanol (108 mg).

Workup

temperatureThe mixture was warmed slowly to room temperature
concentrationAfterwards, the mixture was concentrated onto silica gel
custompurified via column chromatography (24 g silica gel, 0 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-bf1ca68ce69143fb915aec83f305d730
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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