Di-tert-butyl dicarbonate → HCID 57590006, compound

HRID 1784016Notes

Reaction equation

HRID 1784016 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([NH:11][C:12]2[C:13]3[N:14]([N:19]=[CH:20][N:21]=3)[C:15]([Br:18])=[CH:16][N:17]=2)[CH:6]=1)[CH3:2].[O:23](C(OC(C)(C)C)=O)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4](=[O:22])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]([C:12]2[C:13]3[N:14]([N:19]=[CH:20][N:21]=3)[C:15]([Br:18])=[CH:16][N:17]=2)[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:23])[CH:6]=1)[CH3:2]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 57589970HCID 57589970, compound

Product 1

HCID 57590006HCID 57590006, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)benzoic acid ethyl ester (1.79 g, 4.93 mmol) in DCM (20 mL) is stirred under N2 at rt and BOC2O (1.34 g, 6.16 mmol) and DMAP (0.30 g, 2.46 mmol) are added. Stirring is continued for 2 h, when LCMS indicates complete conversion of the starting material. The mixture is filtered and the filtrate is washed with dilute citric acid (pH 6, 5 mL) and brine (5 mL) and dried over Na2SO4. Evaporation of the solvent affords the title compound as a yellow oil (1.87 g, 4.0 mmol) which is used without further purification.

Workup

  1. filtrationThe mixture is filtered
  2. washthe filtrate is washed with dilute citric acid (pH 6, 5 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-e25402d3b56c47beafa2a07d55f06a9a
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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