Dichloromethane → HCID 86670342, compound

HRID 1972459Notes

Reaction equation

Cl.Cl.[F:3][C:4]([F:25])([F:24])[C:5]([C:11]1[CH:12]=[N:13][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][C@@H:18]2[CH3:23])=[N:15][CH:16]=1)([OH:10])[C:6]([F:9])([F:8])[F:7].C(Cl)Cl.C(N(CC)CC)C.[Br:36][C:37]1[S:41][C:40]([S:42](Cl)(=[O:44])=[O:43])=[CH:39][CH:38]=1>O>[Br:36][C:37]1[S:41][C:40]([S:42]([N:20]2[CH2:21][CH2:22][N:17]([C:14]3[N:15]=[CH:16][C:11]([C:5]([OH:10])([C:6]([F:9])([F:8])[F:7])[C:4]([F:3])([F:24])[F:25])=[CH:12][N:13]=3)[C@@H:18]([CH3:23])[CH2:19]2)(=[O:44])=[O:43])=[CH:39][CH:38]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A 250-mL round-bottomed flask was charged with (1,1,1,3,3,3-hexafluoro-2-(2-((2S)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-2-propanol dihydrochloride (1.48 g, 3.55 mmol), 25 mL of CH2Cl2, and triethylamine (1.48 mL, 10.7 mmol). After cooling to 0° C., 5-bromothiophenesulfonyl chloride (0.93 g, 3.55 mmol. Sigma-Aldrich, St. Louis, Mo.) was added and the solution was stirred for 15 min at 0° C. 100 mL of water was then added and the layers were separated. The organics were dried (MgSO4), filtered, and concentrated to give a tar that was purified by column chromatography on silica gel (0-60% EtOAc in hexanes) to give 2-(2-((2S)-4-((5-bromo-2-thiophenyl)sulfonyl)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-1,1,1,3,3,3-hexafluoro-2-propanol (2.01 g) as an off-white foam.

Workup

customthe layers were separated
dry with materialThe organics were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give a tar that
customwas purified by column chromatography on silica gel (0-60% EtOAc in hexanes)

Sources & evidence

ORD record: ord-ef3d86768ea842d4a1600f09668c4f7b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431563B2

Reaction notes

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