Methyl 6-(2-amino-3-carbamoylphenylcarbamoyl)nicotinate → methyl 6-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)nicotinate

HRID 564237Notes

Reaction equation

HRID 564237 reaction equation
[NH2:1][C:2]1[C:7]([C:8](=[O:10])[NH2:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:11][C:12]([C:14]1[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][N:15]=1)=O>C(O)(=O)C>[C:8]([C:7]1[C:2]2[N:1]=[C:12]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][N:15]=3)[NH:11][C:3]=2[CH:4]=[CH:5][CH:6]=1)(=[O:10])[NH2:9]

Participants

3

Reactant 1

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

Product 1

HCID 66759998methyl 6-(4-carbamoyl-1H-benzo[d]imidazol-2-yl)nicotinate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The crude product from EXAMPLE 51A in acetic acid (40 ml) was heated to 90° C. for 1.5 hours. After cooling, the suspension was filtered. The filter cake was washed with acetic acid, and stirred in saturated NaHCO3 for 30 minutes. The solid was filtered, washed with water and ether, and dried under vacuum to provide the title compound as an off-white solid. MS (DCI/NH3) m/z: 297.1 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationthe suspension was filtered
  3. washThe filter cake was washed with acetic acid
  4. filtrationThe solid was filtered
  5. washwashed with water and ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2712366c914a4fd681d3886ddce52fa0
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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