tert-Butyl carbazate → N'-(2-ethyl-6-methyl-pyridine-4-carbonyl)-hydrazinecarboxylic acid tert-butyl ester

HRID 2366121Notes

Reaction equation

HRID 2366121 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([CH3:12])[N:11]=1)[C:6]([OH:8])=O)[CH3:2].[C:13]([O:17][C:18]([NH:20][NH2:21])=[O:19])([CH3:16])([CH3:15])[CH3:14].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.[OH-].[Na+]>[C:13]([O:17][C:18]([NH:20][NH:21][C:6]([C:5]1[CH:9]=[C:10]([CH3:12])[N:11]=[C:3]([CH2:1][CH3:2])[CH:4]=1)=[O:8])=[O:19])([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 4

HCID 70091tert-Butyl carbazateHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 584180972-Ethyl-6-methylisonicotinic acid

Product 1

HCID 67520248N'-(2-ethyl-6-methyl-pyridine-4-carbonyl)-hydrazinecarboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-ethyl-6-methyl-isonicotinic acid (0.53 g, 3.2 mmol), hydrazinecarboxylic acid tert.-butyl ester (0.43 g, 3.2 mmol) and DIPEA (0.85 mL) in DMF (10 mL) is added TBTU (1.23 g, 3.8 mmol). The mixture is stirred at rt for 3 h. The mixture is diluted with 1M aq. NaOH (50 mL) and extracted with Et2O-EA (1:1, 3×50 mL). The organic extracts are dried (Na2SO4), filtered and evaporated to give crude N′-(2-ethyl-6-methyl-pyridine-4-carbonyl)-hydrazinecarboxylic acid tert-butyl ester.

Workup

  1. extractionextracted with Et2O-EA (1:1, 3×50 mL)
  2. dry with materialThe organic extracts are dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-d969ecf458684a4babeb0dbf024b3087
Source dataset
uspto-grants-2014_04
Patent number
US08697732B2

Reaction notes

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