HCID 59408778, compound → HCID 59408762, compound

HRID 1188103Notes

Reaction equation

HRID 1188103 reaction equation
Br[C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:24])[NH:16][C:17]3[CH:22]=[CH:21][C:20](Br)=[CH:19][N:18]=3)=[CH:11][N:10]=2)=[O:7])=[CH:4][N:3]=1>C(N)CC>[CH2:2]([NH:3][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:24])[NH:16][C:17]3[CH:22]=[CH:21][C:20]([NH:8][CH2:6][CH2:5][CH3:4])=[CH:19][N:18]=3)=[CH:11][N:10]=2)=[O:7])=[CH:4][N:3]=1)[CH2:26][CH3:25]

Participants

3

Reactant 1

HCID 59408778HCID 59408778, compound

Product 1

HCID 59408762HCID 59408762, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 7852PropylamineSolvent

Procedure

6-Bromo-N-(5-(5-bromopyridin-2-ylcarbamoyl)pyridin-2-yl)nicotinamide 6 (350 mg, 0.73 mmol) was dissolved in neat n-propylamine. The reaction mixture was heated for 3 days at reflux temperature. Then the solvent was evaporated to give a crude product, which was crystallized in EtOAc to give 6-(propylamino)-N-(5-(5-(propylamino)pyridin-2-ylcarbamoyl)pyridin-2-yl)nicotinamide 7 (122 mg, 38% yield) as a white solid. Mp. 249-250° C.

Workup

  1. temperatureThe reaction mixture was heated for 3 days
  2. temperatureat reflux temperature
  3. customThen the solvent was evaporated
  4. customto give a crude product, which
  5. customwas crystallized in EtOAc

Sources & evidence

ORD record
ord-64b092692e284e8cab89625ec0a47cf3
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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