HCID 22628137, compound → HCID 22628208, compound

HRID 278615Notes

Reaction equation

HRID 278615 reaction equation
[N:1]1([C:6]2[CH:41]=[CH:40][C:9]([C:10]([N:12]3[CH2:17][CH2:16][N:15]([S:18]([C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][C:25]([NH:31]C(OCC(Cl)(Cl)Cl)=O)=[CH:26][CH:27]=5)[CH:22]=4)(=[O:20])=[O:19])[CH2:14][CH2:13]3)=[O:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1>C(O)(=O)C.[Zn]>[NH2:31][C:25]1[CH:24]=[C:23]2[C:28]([CH:29]=[CH:30][C:21]([S:18]([N:15]3[CH2:14][CH2:13][N:12]([C:10](=[O:11])[C:9]4[CH:8]=[CH:7][C:6]([N:1]5[CH:5]=[CH:4][N:3]=[CH:2]5)=[CH:41][CH:40]=4)[CH2:17][CH2:16]3)(=[O:20])=[O:19])=[CH:22]2)=[CH:27][CH:26]=1

Participants

4

Reactant 1

HCID 22628137HCID 22628137, compound

Product 1

HCID 22628208HCID 22628208, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 1-[4-(1-imidazolyl)benzoyl]-4-[7-(2,2,2-trichloroethoxycarbonylamino)naphthalene-2-sulfonyl]piperazine (475 mg) in acetic acid (5 ml) was added zinc powder (1 g), and the mixture was stirred at room temperature for 1 day. The reaction solution was filtered, and the filtrate was concentrated. The residue was dissolved in 0.5 N hydrochloric acid, washed with ethyl acetate and made alkaline with 1 N sodium hydroxide aqueous solution. The precipitate was collected by filtration, and the filtrate was washed with water and dried to give a colorless solid of the title compound (325 mg).

Workup

  1. filtrationThe reaction solution was filtered
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in 0.5 N hydrochloric acid
  4. washwashed with ethyl acetate
  5. filtrationThe precipitate was collected by filtration
  6. washthe filtrate was washed with water
  7. customdried

Sources & evidence

ORD record
ord-e680644c7293461c88949878a5ec9621
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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