Pyridine → HCID 18184538, compound

HRID 1358464Notes

Reaction equation

HRID 1358464 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:23])[CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[C:16]([O:20][CH3:21])=[C:15]([Br:22])[CH:14]=2)=[CH:4][C:3]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][CH:33]=1.N1C=CC=CC=1>C(Cl)Cl>[CH2:25]([O:24][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:23])[CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[C:16]([O:20][CH3:21])=[C:15]([Br:22])[CH:14]=2)[CH:6]=[CH:7][C:2]=1[NH:1][S:38]([C:35]1[CH:36]=[CH:37][C:32]([CH3:42])=[CH:33][CH:34]=1)(=[O:40])=[O:39])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 18184540HCID 18184540, compound

Product 1

HCID 18184538HCID 18184538, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-(4-amino-3-benzyloxy-phenyl)-ethyl]-2-(3,5-dibromo-4-methoxy-phenyl)-acetamide (0.836 g, 0.00152 mol) and p-toluenesulfonyl chloride (0.440 g, 0.00231 mol) in 40 mL of methylene chloride qas added 4 mL of pyridine. The reaction mixture was stirred for 54 h at room temperature, washed with 1N HCl, 1N NaOH solutions, dried over Na2SO4 and evaporated. A residue was crystallized from ethyl acetate-hexanes mixture. Yield 0.933 g (87%).

Workup

  1. washwashed with 1N HCl, 1N NaOH solutions
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customA residue was crystallized from ethyl acetate-hexanes mixture

Sources & evidence

ORD record
ord-e1c0ad1f7c0748c0baf9f5cefd115aad
Source dataset
uspto-grants-2003_07
Patent number
US06596734B1

Reaction notes

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