Triethylamine → HCID 22711277, compound

HRID 352983Notes

Reaction equation

HRID 352983 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:18][CH2:17][N:16]([C:19]([C:21]4[S:22][C:23]5[CH2:24][NH:25][CH2:26][CH2:27][C:28]=5[N:29]=4)=[O:20])[CH2:15][CH2:14]3)(=[O:12])=[O:11])[S:7][C:6]=2[CH:30]=1.Br[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.O.C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:9]=[C:8]([S:10]([N:13]3[CH2:14][CH2:15][N:16]([C:19]([C:21]4[S:22][C:23]5[CH2:24][NH:25][CH:26]([C:32]6[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=6)[CH2:27][C:28]=5[N:29]=4)=[O:20])[CH2:17][CH2:18]3)(=[O:11])=[O:12])[S:7][C:6]=2[CH:30]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 142684-BromopyridineHCID 516892Sodium BicarbonateHCID 22709458HCID 22709458, compound

Product 1

HCID 22711277HCID 22711277, compoundYield 45.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-[(6-chlorobenzo[b]thien-2-yl)sulfonyl]-4-[(4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl]carbonyl]piperazine (200 mg) in N,N-dimethylformamide (2.0 ml) were added 4-bromopyridine (87.0 mg) and triethylamine (150 μl) at room temperature. The resulting mixture was stirred under heat at 120° C. for 12 hours. After concentration of the reaction mixture, methylene chloride (20 ml), a saturated aqueous solution (50 ml) of sodium bicarbonate and water (50 ml) were added to the concentrate to separate it into layers. The water layer thus obtained was extracted with methylene chloride (4×20 ml). The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by preparative thin-layer chromatography (methylene chloride:methanol=20:1) using silica gel, followed by purification by preparative thin-layer chromatography (methylene chloride:acetone:methanol=15:5:1) using silica gel. The purified product was dissolved in methylene chloride, methanol and 1N hydrochloric acid. The resulting solution was concentrated under reduced pressure and dried, whereby the title compound (56.5 mg) was obtained as a pale yellow solid.

Workup

  1. concentrationconcentrate
  2. customto separate it into layers
  3. customThe water layer thus obtained
  4. extractionwas extracted with methylene chloride (4×20 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. customThe residue was purified by preparative thin-layer chromatography (methylene chloride:methanol=20:1)
  9. customfollowed by purification by preparative thin-layer chromatography (methylene chloride:acetone:methanol=15:5:1)
  10. dissolutionThe purified product was dissolved in methylene chloride
  11. concentrationThe resulting solution was concentrated under reduced pressure
  12. customdried

Sources & evidence

ORD record
ord-c1d3055cc1f148e8bee9adbc8cd53e53
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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