HCID 22627980, compound → HCID 22627971, compound

HRID 278626Notes

Reaction equation

HRID 278626 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[S:13]([N:16]1[CH2:21][CH2:20][N:19]([C:22]([C:24]2[S:28][C:27]([C:29]3[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=3)=[N:26][C:25]=2[CH3:35])=[O:23])[CH2:18][CH2:17]1)(=[O:15])=[O:14]>C(O)(=O)C.[Zn]>[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([CH:2]=[C:3]([S:13]([N:16]3[CH2:17][CH2:18][N:19]([C:22]([C:24]4[S:28][C:27]([C:29]5[CH:30]=[CH:31][N:32]=[CH:33][CH:34]=5)=[N:26][C:25]=4[CH3:35])=[O:23])[CH2:20][CH2:21]3)(=[O:14])=[O:15])[CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 22627980HCID 22627980, compound

Product 1

HCID 22627971HCID 22627971, compoundYield 22.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 1-(4,7-dichloroquinoline-3-sulfonyl)-4-[4-methyl-2-(4-pyridyl)-5-thiazolecarbonyl]piperazine (200 mg) and zinc powder (250 mg) in acetic acid (6 ml) was stirred at 80° C. for 2 hours, the mixture was concentrated. The residue was dissolved in dichloromethane-methanol, and insoluble materials were filtered off. The filtrate was concentrated to give brown solid which was successively washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and water, and dried to afford the title compound (43 mg).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was dissolved in dichloromethane-methanol
  3. filtrationinsoluble materials were filtered off
  4. concentrationThe filtrate was concentrated
  5. customto give brown solid which
  6. washwas successively washed with 1 N hydrochloric acid, sodium hydrogen carbonate solution and water
  7. customdried

Sources & evidence

ORD record
ord-d34ac5ecd1414060a43826cdd5ea5db3
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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