(S)-2-aminopropanamide hydrochloride → HCID 9850447, compound

HRID 733324Notes

Reaction equation

HRID 733324 reaction equation
Cl.[NH2:2][C@H:3]([C:5]([NH2:7])=[O:6])[CH3:4].[C:8]([C:10]1[CH:38]=[CH:37][C:13]([CH2:14][C@@:15]2([CH3:36])[N:19]3[C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:21][N:22]=[C:18]3[N:17]([C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=3)[C:16]2=[O:35])=[CH:12][CH:11]=1)#[N:9]>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:8]([C:10]1[CH:11]=[CH:12][C:13]([CH2:14][C@@:15]2([CH3:36])[N:19]3[C:20]([S:23]([NH:2][C@@H:3]([CH3:4])[C:5]([NH2:7])=[O:6])(=[O:25])=[O:24])=[CH:21][N:22]=[C:18]3[N:17]([C:27]3[CH:28]=[C:29]([Cl:34])[CH:30]=[C:31]([Cl:33])[CH:32]=3)[C:16]2=[O:35])=[CH:37][CH:38]=1)#[N:9]

Participants

6

Reactant 2

HCID 2775816(S)-2-aminopropanamide hydrochlorideHCID 12136446HCID 12136446, compound

Product 1

HCID 9850447HCID 9850447, compoundYield 79.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

L-Alaninamide hydrochloride (0.151 g, 1.209 mmol) was dissolved in anhydrous DMF and DMAP (0.197 g, 1.612 mmol) was added to the solution. The reaction mixture was stirred at room temperature for 1 h. Then, (R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl chloride (0.24 g, 0.484 mmol) in anhydrous DMF was added to the reaction mixture and stirred for additional 10 min. The reaction solution was diluted with EtOAc and washed with water, 1 N HCl and then water. The organic phase was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 0.211 g of the title compound as a white scaly solid (M+1, 547.2).

Workup

  1. stirringstirred for additional 10 min
  2. washwashed with water, 1 N HCl
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7bc435663970465cbf9de88add3d6d9f
Source dataset
uspto-grants-2009_09
Patent number
US07589115B2

Reaction notes

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