Picolinic acid → HCID 2771595, compound

HRID 1185251Notes

Reaction equation

HRID 1185251 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[NH2:41][CH:42]([C:48]#[N:49])[C:43]([O:45][CH2:46][CH3:47])=[O:44]>C1COCC1>[C:48]([CH:42]([NH:41][C:7](=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:43]([O:45][CH2:46][CH3:47])=[O:44])#[N:49]

Participants

7

Reactant 5

HCID 1018Picolinic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 288716Ethyl 2-amino-2-cyanoacetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 2771595HCID 2771595, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of picolinic acid (1.23 g, 10 mmol), EDC.HCl (1.91 g, 10 mmol) and HOBT (1.35 g, 10 mmol) in THF (80 mL) was added DIPEA (3.6 g, 30 mmol) at ambient temperature. The reaction mixture was maintained at the same temperature for 1 hr at which time a solution of ethyl 2-amino-2-cyanoacetate (1.28 g, 10 mmol) in THF (5 mL) was added. The reaction mixture was stirred at ambient temperature for additional 6 hr. It was then concentrated, and the residue was purified by silica gel column chromatography (5:1 PE/EtOAc) to give ethyl 2-cyano-2-(picolinamido)acetate (0.7 g, 30%) as yellow solid.

Workup

  1. additionwas added
  2. concentrationIt was then concentrated
  3. customthe residue was purified by silica gel column chromatography (5:1 PE/EtOAc)

Sources & evidence

ORD record
ord-082a46a603dc454491cedad949fded93
Source dataset
uspto-grants-2014_03
Patent number
US08669361B2

Reaction notes

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