Ethyl Acetate → HCID 57920581, compound

HRID 57177Notes

Reaction equation

HRID 57177 reaction equation
[S:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[NH:10][S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12].[Cl:20]N1C(=O)CCC1=O.C(OCC)(=O)C>CN(C=O)C>[Cl:20][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[S:1][C:2]=1[NH:10][S:11]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:12])=[O:13]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 57920381HCID 57920381, compound

Product 1

HCID 57920581HCID 57920581, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To compound 147-F (0.26 g, 0.643 mmol) in DMF (1 mL) under argon at ambient temperature was added N-chlorosuccinimide (94.4 mg, 0.707 mmol) and the reaction mixture was stirred for 16 h. Ethyl acetate was added, the mixture washed with H2O (2×), brine, evaporated under reduced pressure and purified by reverse phase pHPLC (C18) to afford 0.072 g of compound 813-A as a tan solid. 1H-NMR (DMSO-d6): δ 7.50 (dd, 1H), 7.56-7.65 (m, 2H), 7.65-7.74 (m, 1H), 7.81-7.89 (m, 2H), 8.00 (dd, 1H), 8.58 (dd, 1H).

Workup

  1. washthe mixture washed with H2O (2×), brine
  2. customevaporated under reduced pressure
  3. custompurified by reverse phase pHPLC (C18)

Sources & evidence

ORD record
ord-9139838a314645aea9d9a60f7dd3b687
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Reaction notes

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