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Citric Acid → {2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester

HRID 11565
Notes
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Reaction equation

HRID 11565 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][N:4]=1)#[N:2].CN1CCOCC1.ClC(OCC(C)C)=O.[C:27]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH2:41])([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[C:30]([O:29][C:27](=[O:28])[NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[NH:41][C:7]([C:6]1[CH:5]=[N:4][C:3]([C:1]#[N:2])=[CH:11][CH:10]=1)=[O:9])([CH3:33])([CH3:31])[CH3:32]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 311Citric AcidHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 676311N-(tert-Butoxycarbonyl)-1,2-phenylenediamineHCID 27611086-Cyanopyridine-3-carboxylic acid

Product 1

HCID 69655660{2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester
Yield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 444 mg (3.0 mmol) 6-cyano-nicotinic acid and 354 mg (3.5 mmol) N-methylmorpholine in 7 ml DMF at −20° C. was added 450 mg (3.3 mmol) isobutyl chloroformate. The reaction mixture was warmed to 5° C., and 625 mg (3.0 mmol) mono-boc-ortho-phenylenediamine was added. The reaction mixture was warmed to rt overnight and then poured into 50 ml 5% aqueous citric acid. The aqueous phase was extracted with ethyl acetate, the combined organic phases were washed with bicarbonate and brine and dried over Na2SO4. The solvent was evaporated and the residue was subjected to silica gel chromatography (petrol ether/ethyl acetate 2:1) to yield 795 mg (2.35 mmol) {2-[(6-Cyano-pyridine-3-carbonyl)-amino]-phenyl}-carbamic acid t-butyl ester; mp.183–184° C.

Workup

  1. temperatureThe reaction mixture was warmed to rt overnight
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. washthe combined organic phases were washed with bicarbonate and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0fe46712cd1942958efdafa5a636c66d
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07098247B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes