Ammonia → HCID 178520222, compound

HRID 2421497Notes

Reaction equation

HRID 2421497 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[C:14]2[NH:15][C:16]([C:18]3[C:19](=[O:34])[NH:20][CH:21]=[CH:22][C:23]=3[NH:24][CH2:25][C@@H:26]([OH:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:17][C:13]=2[CH:12]=[CH:11][CH:10]=1.[C:35]1([CH2:41][C:42](Cl)=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.N>C1COCC1>[OH:33][C@@H:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:25][NH:24][C:23]1[CH:22]=[CH:21][NH:20][C:19](=[O:34])[C:18]=1[C:16]1[NH:15][C:14]2[C:9]([NH:8][C:42](=[O:43])[CH2:41][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:10][CH:11]=[CH:12][C:13]=2[N:17]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 178507439HCID 178507439, compound

Product 1

HCID 178520222HCID 178520222, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (0.058 g, 0.416 mmol) 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 phenylacetyl chloride (0.051 g 0.32 mmol) in THF (2 ml) and the reaction stirred at room temperature. After 20 hours methanolic ammonia was added (5 ml) and the reaction stirred for a further 20 hours. The reaction mixture was concentrated under reduced pressure and the crude solid washed with acetonitrile water (1:1; 10 ml) to give the desired product (0.034 g; 43%).

Workup

  1. customPrepared
  2. stirringthe reaction stirred for a further 20 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. washthe crude solid washed with acetonitrile water (1:1; 10 ml)

Sources & evidence

ORD record
ord-67961b04f6994cd299c3e58bd9bf69ef
Source dataset
uspto-grants-2011_06
Patent number
US07956190B2

Reaction notes

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