Ethyl Acetate → HCID 59979236, compound

HRID 733327Notes

Reaction equation

HRID 733327 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][C@@:8]2([CH3:29])[N:12]3[C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:14][N:15]=[C:11]3[N:10]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)[C:9]2=[O:28])=[CH:5][CH:4]=1)#[N:2].CCO[C:35]([CH3:37])=[O:36]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:1]([C:3]1[CH:31]=[CH:30][C:6]([CH2:7][C@@:8]2([CH3:29])[N:12]3[C:13]([S:16]([NH:12][C@@H:8]([CH3:7])[C:9]([NH:10][CH2:37][CH2:35][OH:36])=[O:28])(=[O:18])=[O:17])=[CH:14][N:15]=[C:11]3[N:10]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)[C:9]2=[O:28])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 12136446HCID 12136446, compound

Product 1

HCID 59979236HCID 59979236, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of above amine salt (0.043 g, 0.254 mmol) in anhydrous DMF, was added DMAP (0.037 g, 0.303 mmol). The reaction mixture was stirred at room temperature for 1 h. (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 (0.036 g, 0.073 mmol) was then added to the reaction mixture and stirred for another 2 h. The reaction mixture was diluted with EtOAc and washed with 1 N HCl and saturated NaHCO3. The organic phase was dried over Na2SO4 and concentrated. The residue was purified by silica gel preparative thin layer chromatography to afford 0.035 g of the title compound as a white foam (M+1, 591.1).

Workup

  1. additionwas then added to the reaction mixture
  2. washwashed with 1 N HCl and saturated NaHCO3
  3. dry with materialThe organic phase was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel preparative thin layer chromatography

Sources & evidence

ORD record
ord-3831c467782f473baaf7911c3dcae40b
Source dataset
uspto-grants-2009_09
Patent number
US07589115B2

Reaction notes

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