Pyridine → HCID 178492634, compound

HRID 2421498Notes

Reaction equation

HRID 2421498 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[C:13]2[NH:14][C:15]([C:17]3[C:18](=[O:33])[NH:19][CH:20]=[CH:21][C:22]=3[NH:23][CH2:24][C@@H:25]([OH:32])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:16][C:12]=2[CH:11]=[CH:10][CH:9]=1.Cl[C:35]([O:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=1)=[O:36]>C1COCC1>[CH3:45][O:44][C:41]1[CH:42]=[CH:43][C:38]([O:37][C:35](=[O:36])[NH:7][C:8]2[C:13]3[NH:14][C:15]([C:17]4[C:18](=[O:33])[NH:19][CH:20]=[CH:21][C:22]=4[NH:23][CH2:24][C@@H:25]([OH:32])[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)=[N:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 82128Carbonochloridic acid, 4-methoxyphenyl esterHCID 178507439HCID 178507439, compound

Product 1

HCID 178492634HCID 178492634, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Pyridine (2.0 ml) was added to a solution of 3-(7-amino-1H-benzoimidazol-2-yl)-4-((S)-2-hydroxy-2-phenyl-ethylamino)-1H-pyridin-2-one (0.060 g, 0.166 mmol) (Prepared according to the general method for the intermediates of formula II and III above) and 4-methoxyphenyl chloroformate (0.062 g, 0.32 mmol) in THF (2 ml) and the reaction stirred at room temperature. After 20 hours the reaction was concentrated and the crude mixture was purified by column chromatography (1-2% methanol, dichloromethane) to give the desired product (0.028 g; 33%).

Workup

  1. customPrepared
  2. concentrationAfter 20 hours the reaction was concentrated
  3. customthe crude mixture was purified by column chromatography (1-2% methanol, dichloromethane)

Sources & evidence

ORD record
ord-4519a57c104547968367da7ccc5d2386
Source dataset
uspto-grants-2011_06
Patent number
US07956190B2

Reaction notes

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