Water → HCID 68934004, compound

HRID 1260978Notes

Reaction equation

HRID 1260978 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([C:6]([N:8]([C@@H:10]2[CH2:15][CH2:14][N:13]([N:16]=O)[CH2:12][C@H:11]2[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH3:9])=[O:7])=[CH:4][CH:3]=1.O.Cl.C(OCC)(=O)C>C(O)(=O)C.[Zn]>[ClH:1].[NH2:16][N:13]1[CH2:14][CH2:15][C@@H:10]([N:8]([CH3:9])[C:6](=[O:7])[C:5]2[CH:26]=[CH:27][C:2]([Cl:1])=[CH:3][CH:4]=2)[C@H:11]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)[CH2:12]1

Participants

6

Reactant 3

HCID 962WaterHCID 21866389Hydrogen chloride-ethyl acetateHCID 86631404HCID 86631404, compound

Product 1

HCID 68934004HCID 68934004, compoundYield 153.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of the compound obtained in Example 548 (300 mg) in acetic acid (3 mL) was added Zn powder (229 mg), and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the resultant product was extracted with ethyl acetate. The organic layer was washed with water and dried, and the solvent was evaporated under reduced pressure. The obtained residue was treated with 1 equivalent of 4N hydrogen chloride/ethyl acetate to give the title compound (243 mg, 76%) as a white powder.

Workup

  1. extractionthe resultant product was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-bc2dfe95b7f64c5998dca4e1ac3a7994
Source dataset
uspto-grants-2013_06
Patent number
US08470816B2

Reaction notes

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