Triethylamine → HCID 22710115, compound

HRID 1061034Notes

Reaction equation

HRID 1061034 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15](C(O)=O)=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.Cl.[Cl:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[CH:45]=[C:44]([S:49]([N:52]1[CH2:57][CH2:56][NH:55][CH2:54][CH2:53]1)(=[O:51])=[O:50])[CH:43]=[CH:42]2.[OH-:58].[Na+].C([N:62]([CH2:65]C)CC)C>C1C=CC=CC=1.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([NH:62][C:65]([N:55]3[CH2:54][CH2:53][N:52]([S:49]([C:44]4[CH:43]=[CH:42][C:41]5[C:46](=[CH:47][CH:48]=[C:39]([Cl:38])[CH:40]=5)[CH:45]=4)(=[O:50])=[O:51])[CH2:57][CH2:56]3)=[O:58])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 177503995-(tert-Butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acidHCID 227097661-(6-Chloronaphth-2-ylsulphonyl)piperazine hydrochloride

Product 1

HCID 22710115HCID 22710115, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Procedure

In benzene (10 ml), 5-tert-butoxycarbonyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-carboxylic acid (283 mg) was dissolved, followed by the addition of triethylamine (0.14 ml) and diphenylphosphoryl azide (0.21 g). The resulting mixture was heated under reflux for 2 hours. After cooling to room temperature, the reaction mixture was added with 1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride (347 mg), followed by heating overnight under reflux. After the reaction mixture was cooled to room temperature, dichloromethane and a 3N aqueous sodium hydroxide solution were added thereto to extract an organic layer. The organic layer so extracted was washed with 0.5N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and saturated saline and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1˜2:1), whereby the title compound (284 mg, 48%) was obtained.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureby heating overnight
  4. temperatureunder reflux
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. extractionto extract an organic layer
  7. extractionThe organic layer so extracted
  8. washwas washed with 0.5N hydrochloric acid
  9. dry with materiala saturated aqueous solution of sodium bicarbonate and saturated saline and dried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1˜2:1), whereby the title compound (284 mg, 48%)
  12. customwas obtained

Sources & evidence

ORD record
ord-b4d61bfec60c47979041468f4cbac279
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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