Dimethylformamide → 1-[(5-Bromopyrimidin-2-yl)carbonyl]-4-[(6-chlorobenzo[b]thiophen-2-yl)sulfonyl]-2-(2-methylpropyl)piperazine

HRID 352827Notes

Reaction equation

HRID 352827 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:8]=[CH:9][C:10]2[CH:14]=[C:13]([S:15]([N:18]3[CH2:23][CH2:22][NH:21][CH:20]([CH2:24][CH:25]([CH3:27])[CH3:26])[CH2:19]3)(=[O:17])=[O:16])[S:12][C:11]=2[CH:28]=1.F[P-](F)(F)(F)(F)F.[Br:36][P+](N1CCCC1)(N1CCCC1)N1CCCC1.Br[C:54]1[CH:59]=[CH:58][N:57]=[C:56]([C:60]([OH:62])=O)[N:55]=1>C(N(CC)CC)C>[Br:36][C:59]1[CH:54]=[N:55][C:56]([C:60]([N:21]2[CH2:22][CH2:23][N:18]([S:15]([C:13]3[S:12][C:11]4[CH:28]=[C:7]([Cl:6])[CH:8]=[CH:9][C:10]=4[CH:14]=3)(=[O:17])=[O:16])[CH2:19][CH:20]2[CH2:24][CH:25]([CH3:26])[CH3:27])=[O:62])=[N:57][CH:58]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 2733179PyBroPHCID 227099811-[(6-Chlorobenzo[b]thiophen-2-yl)sulfonyl]-3-(2-methylpropyl)piperazineHCID 227104484-Bromopyrimidine-2-carboxylic acid

Product 1

HCID 227099031-[(5-Bromopyrimidin-2-yl)carbonyl]-4-[(6-chlorobenzo[b]thiophen-2-yl)sulfonyl]-2-(2-methylpropyl)piperazine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To an N,N-dimethylformamide solution (60 ml) of 1-[(6-chlorobenzo[b]thiophen-2-yl)sulfonyl]-3-(2-methylpropyl)piperazine (2.55 mg) were added bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (607 mg, 1.17 mmol), (4-bromopyrimidin-2-yl)carboxylic acid (237 mg) and triethylamine (118 mg), followed by stirring at room temperature for 13 hours. After completion of the reaction, the solvent was distilled off under reduced pressure. Distilled water and methylene chloride were added to the residue. The water layer thus obtained was extracted three times with methylene chloride. The organic layers were combined and washed with distilled water. After drying over anhydrous magnesium sulfate, the solvent was distilled under off under reduced pressure. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:100), followed by crystallization from ethyl acetate—diethyl ether, whereby the title compound (326 mg) was obtained as brown crystals.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionDistilled water and methylene chloride were added to the residue
  4. customThe water layer thus obtained
  5. extractionwas extracted three times with methylene chloride
  6. washwashed with distilled water
  7. dry with materialAfter drying over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled under off under reduced pressure
  9. customfollowed by crystallization from ethyl acetate—diethyl ether, whereby the title compound (326 mg)
  10. customwas obtained as brown crystals

Sources & evidence

ORD record
ord-36e31dfb37fb424b875c7f62aebb0148
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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