Ethyl Acetate → HCID 135763129, compound

HRID 1792578Notes

Reaction equation

HRID 1792578 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:17]([C:40]4[CH:45]=[CH:44][C:43]([O:46]COCC[Si](C)(C)C)=[CH:42][CH:41]=4)=[N:18][N:19]([C:21]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:20]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1.CN(C)P(N(C)C)N(C)C.C(OCC)(=O)C.[Cl-].[NH4+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH:12]=[C:13]([C:16]3[C:17]([C:40]4[CH:41]=[CH:42][C:43]([OH:46])=[CH:44][CH:45]=4)=[N:18][N:19]([C:21]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH:20]=3)[CH:14]=[CH:15][C:10]2=[N:9][CH:8]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 15355Hexamethylphosphorous triamideHCID 25517Ammonium ChlorideHCID 22031322HCID 22031322, compound

Product 1

HCID 135763129HCID 135763129, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.23 g 3-(pyridin-2-yl)-6-{3-[4-(2-trimethylsilanylethoxymethoxy)phenyl]-1-trityl-1H-pyrazol-4-yl}imidazo[1,2-a]pyridin (compound in Example 352), 8.5 mL tetrabutylammoniumchloride (1 M tetrahydrofuran solution) and 10 mL hexamethyl phosphorous acid triamide was stirred at 80° C. for 2 hours. Ethyl acetate, an aqueous saturated ammonium chloride solution and water were added to the reaction solution, and the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate, the solvent was evaporated, the resulting residue was triturated with diisopropyl ether, and the crystals were collected by filtration to give 1.01 g of the title compound as white crystals.

Workup

  1. customthe organic layer was separated
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated
  4. customthe resulting residue was triturated with diisopropyl ether
  5. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-b74ac904e2ff44ee99694a628a6a8b7a
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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