Triethylamine → HCID 17915734, compound

HRID 346678Notes

Reaction equation

HRID 346678 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([C:24]([O:26][CH3:27])=[O:25])=[C:19]([CH:23]=1)[C:20](O)=[O:21])(=[O:14])=[O:13])[CH:6]=[CH:5]2.C(Cl)(=O)C(Cl)=O.[N:34]1[CH:39]=[CH:38][C:37]([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:36][CH:35]=1.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([C:24]([O:26][CH3:27])=[O:25])=[C:19]([CH:23]=1)[C:20]([N:43]1[CH2:44][CH2:45][N:40]([C:37]3[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=3)[CH2:41][CH2:42]1)=[O:21])(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 705171-(4-Pyridyl)piperazineHCID 54312453HCID 54312453, compound

Product 1

HCID 17915734HCID 17915734, compoundYield 44.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

5-(6-Bromonaphth-2-ylsulphonyl)-2-methoxycarbonylbenzoic acid(97 mg) was dissolved in dichloromethane (1 ml.). Oxalyl chloride (126 mg) was added and the mixture stirred at ambient temperature for 1 hour. The mixture was evaporated to give a solid which was redissolved in dichloromethane (1 ml) and added to a solution of N-(4-pyridyl)piperazine (34 mg) and triethylamine (108 mg) in dichloromethane (2 ml). After stirring for 2 hours at ambient temperature the mixture was diluted with ethyl acetate (100 ml), washed with water (2×25 ml), dried (MgSO4) and evaporated to give an oil, which was further purified by chromatography (Mega Bond Elut column, eluted with dichloromethane containing an increasing proportion of methanol, 0-5%) to give 1-[5-(6-bromonaphth-2-ylsulphonyl)-2-methoxycarbonylbenzoyl]-4-(4-pyridyl)piperazine (55 mg);

Workup

  1. customThe mixture was evaporated
  2. customto give a solid which
  3. stirringAfter stirring for 2 hours at ambient temperature the mixture
  4. washwashed with water (2×25 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give an oil, which
  8. customwas further purified by chromatography (Mega Bond Elut column
  9. washeluted with dichloromethane containing an increasing proportion of methanol, 0-5%)

Sources & evidence

ORD record
ord-95f4b55bbb1e4cf4911745e9e171b0d5
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Reaction notes

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