Triethylamine → HCID 22710115, compound

HRID 352849Notes

Reaction equation

HRID 352849 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 8471Triethylamine2×HCID 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]pyridine-2-carboxylic acid (WO94/21599)(283 mg) was dissolved. To the resulting solution, triethylamine (0.14 ml) and diphenylphosphoryl azide (0.21 mg) were added, followed by heating under reflux for 2 hours. After the reaction mixture was cooled to room temperature, 1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine hydrochloride (347 mg) and triethylamine (0.28 ml) were added and the mixture was heated under reflux overnight. After cooling to room temperature, to the reaction mixture was added dichloromethane and a 3N aqueous sodium hydroxide solution. The resulting mixture was separated and aqueous layer was extracted with dichloromethane. The combined organic layer thus extracted was washed with 0.5N hydrochloric acid, a saturated aqueous solution of sodium bicarbonate and saturated aqueous NaCl solution, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1 to 2:1), whereby the title compound (284 mg, 48%) was obtained.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux overnight
  5. temperatureAfter cooling to room temperature, to the reaction mixture
  6. customThe resulting mixture was separated
  7. extractionaqueous layer was extracted with dichloromethane
  8. extractionThe combined organic layer thus extracted
  9. washwas washed with 0.5N hydrochloric acid
  10. dry with materiala saturated aqueous solution of sodium bicarbonate and saturated aqueous NaCl solution, dried over anhydrous sodium sulfate
  11. distillationdistilled under reduced pressure
  12. customto remove the solvent
  13. customThe residue was purified by chromatography on a silica gel column (hexane:ethyl acetate=3:1 to 2:1), whereby the title compound (284 mg, 48%)
  14. customwas obtained

Sources & evidence

ORD record
ord-ba4a35f6ab2b4f7caa22b0d9e295c2cd
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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