4-Toluenesulfonyl chloride → HCID 86667821, compound

HRID 538982Notes

Reaction equation

HRID 538982 reaction equation
[CH3:1][Si:2]([CH3:29])([CH3:28])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:19]=[N:20][N:21]3[CH:26]=[CH:25][C:24]([OH:27])=[N:23][C:22]=23)=[CH:14][CH:13]=1.[S:30](Cl)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31].CCN(CC)CC.CCOC(C)=O>O1CCOCC1>[CH3:37][C:36]1[CH:38]=[CH:39][C:33]([S:30]([O:27][C:24]2[CH:25]=[CH:26][N:21]3[N:20]=[CH:19][C:18]([C:15]4[CH:14]=[CH:13][C:12]([C:8]5[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:29])([CH3:28])[CH3:1])[CH:11]=[CH:10][N:9]=5)=[CH:17][CH:16]=4)=[C:22]3[N:23]=2)(=[O:32])=[O:31])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chloride2×HCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 178504246HCID 178504246, compound

Product 1

HCID 86667821HCID 86667821, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-ol (15.0 mg, 0.0368 mmol), tosyl chloride (7.0 mg, 0.0368 mmol) and NEt3 (5.13 μL, 0.037 mmol) in dioxane (2 mL) was heated at 80° C. for 18 hours. Additional portions of tosyl chloride (7.0 mg, 0.037 mmol) and NEt3 (5.1 μL, 0.037 mmol) were added and the mixture continued to heat at 80° C. for 12 hours. The cooled reaction mixture was poured into EtOAc and extracted with 10% HCl. The organic extract was dried (Na2SO4), filtered, and concentrated. Purification of the crude material by column chromatography, eluting with 1-2% MeOH/dichloromethane, afforded 3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl 4-methylbenzenesulfonate as a brown-yellow film (19.0 mg, 92%). LCMS (APCI+) m/z 562 [M+H]+.

Workup

  1. temperatureto heat at 80° C. for 12 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with 10% HCl
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the crude material by column chromatography
  9. washeluting with 1-2% MeOH/dichloromethane

Sources & evidence

ORD record
ord-a048f4f2f9824d5ca1ae32776bc0085d
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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