Ammonium Chloride → 1-[(5-Bromopyrimidin-2-yl)carbonyl]-4-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]-2-ethylpiperazine

HRID 352802Notes

Reaction equation

HRID 352802 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.C(N(C(C)C)CC)(C)C.[Cl:26][C:27]1[CH:28]=[CH:29][C:30]2[CH:34]=[C:33]([S:35]([N:38]3[CH2:43][CH2:42][NH:41][CH:40]([CH2:44][CH3:45])[CH2:39]3)(=[O:37])=[O:36])[S:32][C:31]=2[CH:46]=1.[Cl-].[NH4+]>C(Cl)Cl.CN(C)C=O>[Br:1][C:2]1[CH:7]=[N:6][C:5]([C:8]([N:41]2[CH2:42][CH2:43][N:38]([S:35]([C:33]3[S:32][C:31]4[CH:46]=[C:27]([Cl:26])[CH:28]=[CH:29][C:30]=4[CH:34]=3)(=[O:37])=[O:36])[CH2:39][CH:40]2[CH2:44][CH3:45])=[O:10])=[N:4][CH:3]=1

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 164629705-Bromopyrimidine-2-carboxylic acidHCID 227097651-[(6-Chlorobenzo[b]thien-2-yl)sulfonyl]-3-ethylpiperazine

Product 1

HCID 227113111-[(5-Bromopyrimidin-2-yl)carbonyl]-4-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]-2-ethylpiperazine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Under an argon atmosphere, N,N-dimethylformamide (0.15 ml) was added to a methylene chloride solution (25 ml) of 5-bromopyrimidine-2-carboxylic acid (455 mg) was added and the resulting mixture was ice cooled. Oxalyl chloride (564 mg) was added and the resulting mixture was stirred for 30 minutes under ice cooling. The resulting solution, together with diisopropylethylamine (2.7 ml), was added to a methylene chloride solution (25 ml) of 1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]-3-ethylpiperazine (255 mg), followed by stirring at 0° C. for 1 hour. The reaction mixture was added successively with a saturated aqueous solution of ammonium chloride and distilled water. The water layer was extracted three times with methylene chloride. The organic layers were combined, washed three times with distilled water, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:100), whereby the title compound (308 mg) was obtained as a pale yellow oil.

Workup

  1. additionwas added
  2. temperaturecooled
  3. stirringby stirring at 0° C. for 1 hour
  4. distillationdistilled water
  5. extractionThe water layer was extracted three times with methylene chloride
  6. washwashed three times with distilled water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customwas obtained as a pale yellow oil

Sources & evidence

ORD record
ord-2cbbaad864524dbf9fbf4fd18180598d
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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