Dichloromethane → HCID 56932986, compound

HRID 1972358Notes

Reaction equation

HRID 1972358 reaction equation
Cl.Cl.[F:3][C:4]([F:22])([F:21])[C:5]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][NH:17][CH2:16][C@@H:15]2[CH3:20])=[N:12][CH:13]=1)([OH:7])[CH3:6].C(Cl)Cl.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[S:31](Cl)(=[O:33])=[O:32]>O>[F:22][C:4]([F:3])([F:21])[C:5]([C:8]1[CH:9]=[N:10][C:11]([N:14]2[CH2:19][CH2:18][N:17]([S:31]([C:27]3[S:26][CH:30]=[CH:29][CH:28]=3)(=[O:33])=[O:32])[CH2:16][C@@H:15]2[CH3:20])=[N:12][CH:13]=1)([OH:7])[CH3:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 855182-Thiophenesulfonyl chlorideHCID 66582443HCID 66582443, compound

Product 1

HCID 56932986HCID 56932986, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round-bottomed flask was charged with 1,1,1-trifluoro-2-(2-((2S)-2-methyl-1-piperazinyl)-5-pyrimidinyl)-2-propanol dihydro chloride (0.250 g, 0.763 mmol) and 10 mL of CH2Cl2. To this was added 2-thiophenesulfonyl chloride (0.153 g, 0.839 mmol, Sigma-Aldrich, St. Louis, Mo.). After 15 min, the mixture was diluted with water (50 mL) and extracted with CH2Cl2 (2×50 mL). The combined extracts were dried (MgSO4), concentrated, and purified via column chromatography (40 g of silica, 0 to 50% EtOAc in hexanes) to give 1,1,1-trifluoro-2-(2-((2S)-2-methyl-4-(2-thiophenylsulfonyl)-1-piperazinyl)-5-pyrimidinyl)-2-propanol (0.125 g) as mixture of two isomers.

Workup

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography (40 g of silica, 0 to 50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-3a48f3cd477447da9178c2858d10c0d7
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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