Dimethyl Sulfoxide → HCID 131734588, compound

HRID 595313Notes

Reaction equation

HRID 595313 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][CH2:19][CH:20]([OH:44])[CH2:21][N:22]1[CH:26]=[C:25]([C:27]2[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([NH:34][C:35]3[N:40]=[C:39]([CH:41]([F:43])[F:42])[CH:38]=[CH:37][N:36]=3)[CH:28]=2)[CH:24]=[N:23]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.O>[Si:11]([O:18][CH2:19][C:20](=[O:44])[CH2:21][N:22]1[CH:26]=[C:25]([C:27]2[CH:32]=[C:31]([CH3:33])[CH:30]=[C:29]([NH:34][C:35]3[N:40]=[C:39]([CH:41]([F:42])[F:43])[CH:38]=[CH:37][N:36]=3)[CH:28]=2)[CH:24]=[N:23]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 131734587HCID 131734587, compound

Product 1

HCID 131734588HCID 131734588, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.21 mL, 2.39 mmol) was added to a solution of dimethyl sulfoxide (0.34 mL, 4.78 mmol) in methylene chloride (20 mL) at −78° C. The mixture was stirred for 10 minutes and 1-((tert-butyldimethylsilyl)oxy)-3-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)propan-2-ol (780 mg, 1.59 mmol) was added. After stirring for additional 15 minutes, triethylamine (1.11 mL, 7.97 mmol) was added. The mixture was allowed to warm to room temperature for 2 h. Water was added to the mixture, which was then extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-40% EtOAc/Hexane) to afford 1-((tert-butyldimethylsilyl)oxy)-3-(4-(3-((4-(difluoromethyl)pyrimidin-2-yl)amino)-5-methylphenyl)-1H-pyrazol-1-yl)propan-2-one. MS ESI calc'd. for C24H32F2N5O2Si [M+H]+ 488. found 488.

Workup

  1. stirringAfter stirring for additional 15 minutes
  2. extractionwas then extracted with methylene chloride
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (0-40% EtOAc/Hexane)

Sources & evidence

ORD record
ord-d56d011d81764540a83304bb7cd723f0
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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