Potassium Carbonate → HCID 22235550, compound

HRID 1743715Notes

Reaction equation

HRID 1743715 reaction equation
[CH:1]12[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:5]([CH2:6][CH2:7]1)[CH2:4][NH:3][CH2:2]2.C([O-])([O-])=O.[K+].[K+].CC1C=CC(S(O[CH2:33][CH2:34][CH2:35][NH:36][C:37]2[CH:42]=[CH:41][C:40]([C:43]#[N:44])=[CH:39][CH:38]=2)(=O)=O)=CC=1.C(Cl)Cl.CCOC(C)=O>CN(C=O)C>[C:43]([C:40]1[CH:41]=[CH:42][C:37]([NH:36][CH2:35][CH2:34][CH2:33][N:3]2[CH2:4][CH:5]3[N:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:1]([CH2:7][CH2:6]3)[CH2:2]2)=[CH:38][CH:39]=1)#[N:44]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 157409088-Boc-3,8-diaza-bicyclo(3.2.1)octaneHCID 21226138Dichloromethane ethylacetateHCID 218676523-(4-Cyanoanilino)propyl 4-methylbenzenesulfonate

Product 1

HCID 22235550HCID 22235550, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of tert-butyl 3,8-diazabicyclo[3.2.1]octane-8-carboxylate (3.5 g, 16.5 mmol; from Preparation B above) in DMF (75 mL) was added K2CO3 and 3-(4-cyanoanilino)propyl 4-methylbenzenesulfonate (5.5 g, 16.5 mmol; from Preparation D, step (b) above). The resulting solution was warmed to 90° C., stirred for 5 h, cooled and concentrated in vacuo. The residue was suspended in H2O and extracted with CH2Cl2 (3×). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo to give an oil. Flash chromatography on silica gel eluting with CH2Cl2:EtOAc (3:1) gave 4.7 g (77%) of the title compound as a solid.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organics were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an oil

Sources & evidence

ORD record
ord-02f91c32991447ceb80585b9f6c6cfe1
Source dataset
uspto-grants-2006_03
Patent number
US07012074B2

Reaction notes

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