Dimethylformamide → N-(2-amino-3-carbamoylphenyl)-6-(oxazol-5-yl)nicotinamide

HRID 564235Notes

Reaction equation

HRID 564235 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)(N1C=CN=C1)=[O:2].[NH2:13][C:14]1[C:22]([NH2:23])=[CH:21][CH:20]=[CH:19][C:15]=1[C:16]([NH2:18])=[O:17].[CH3:24][N:25]([CH3:28])C=O>N1C=CC=CC=1>[NH2:13][C:14]1[C:15]([C:16](=[O:17])[NH2:18])=[CH:19][CH:20]=[CH:21][C:22]=1[NH:23][C:16](=[O:17])[C:15]1[CH:14]=[CH:22][C:24]([C:11]2[O:2][CH:1]=[N:8][CH:12]=2)=[N:25][CH:28]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 104870292,3-Diaminobenzamide

Product 1

HCID 66759969N-(2-amino-3-carbamoylphenyl)-6-(oxazol-5-yl)nicotinamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of EXAMPLE 50A (60.0 mg, 0.316 mmol) in a mixture of pyridine (1.5 mL) and N,N-dimethylformamide (1.5 mL) was treated with 1,1′-carbonyldiimidazole (56.3 mg, 0.347 mmol) at 45° C. for 2 hours. After cooling, 2,3-diaminobenzamide (HCl salt) (70.7 mg, 0.316 mmol) was added and the mixture stirred at room temperature for 5 hours. After concentration, the residue was treated with 20% brine and ethyl acetate. The solid was filtered, washed with ethyl acetate and water, and dried under vacuum to provide the title compound. This material was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. concentrationAfter concentration
  3. additionthe residue was treated with 20% brine and ethyl acetate
  4. filtrationThe solid was filtered
  5. washwashed with ethyl acetate and water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-961c1625352044ec8da9c7c71bcbf905
Source dataset
uspto-grants-2011_11
Patent number
US08067613B2

Reaction notes

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