1,1'-Carbonyldiimidazole → Methyl 6-(2-amino-3-carbamoylphenylcarbamoyl)nicotinate

HRID 564236Notes

Reaction equation

HRID 564236 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:26][C:27]1[C:35]([NH2:36])=[CH:34][CH:33]=[CH:32][C:28]=1[C:29]([NH2:31])=[O:30]>N1C=CC=CC=1.CN(C)C=O>[NH2:26][C:27]1[C:28]([C:29](=[O:30])[NH2:31])=[CH:32][CH:33]=[CH:34][C:35]=1[NH:36][C:11]([C:8]1[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][N:9]=1)=[O:13]

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 104870292,3-Diaminobenzamide

Product 1

HCID 66759270Methyl 6-(2-amino-3-carbamoylphenylcarbamoyl)nicotinate

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(methoxycarbonyl)picolinic acid (3.33 g, 18.4 mmol) in a mixture of pyridine (20 mL) and N,N-dimethylformamide (35 mL) was treated with 1,1′-carbonyldiimidazole (3.28 g, 20.2 mmol) at 45° C. for 2 hours. After cooling, 2,3-diaminobenzamide (HCl salt) (4.12 g, 18.4 mmol) was added and the mixture stirred at room temperature overnight. The mixture was concentrated and the residue used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. concentrationThe mixture was concentrated
  3. customthe residue used in the next step without further purification

Sources & evidence

ORD record
ord-aa85998bb25d40529f7b57a02a3e4f6e
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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