Diethyl Ether → HCID 22709995, compound

HRID 352978Notes

Reaction equation

HRID 352978 reaction equation
C(O[C:6]([CH:8]1[N:13]([CH3:14])[CH2:12][C:11]2[S:15][C:16]([C:18]([N:20]3[CH2:25][CH2:24][N:23]([S:26]([C:29]4[NH:30][C:31]5[C:36]([CH:37]=4)=[CH:35][C:34]([Cl:38])=[CH:33][CH:32]=5)(=[O:28])=[O:27])[CH2:22][CH:21]3[C:39](=[O:42])[NH:40][CH3:41])=[O:19])=[N:17][C:10]=2[CH2:9]1)=O)(C)(C)C.C(OCC)C>Cl.C(O)C>[ClH:38].[Cl:38][C:34]1[CH:35]=[C:36]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29]([S:26]([N:23]1[CH2:24][CH2:25][N:20]([C:18]([C:16]3[S:15][C:11]4[CH2:12][N:13]([CH3:14])[CH:8]([CH3:6])[CH2:9][C:10]=4[N:17]=3)=[O:19])[CH:21]([C:39](=[O:42])[NH:40][CH3:41])[CH2:22]1)(=[O:28])=[O:27])=[CH:37]2

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 22711505HCID 22711505, compound

Product 1

HCID 22709995HCID 22709995, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

In a saturated solution of hydrochloride in ethanol (2 ml) was dissolved 1-[[6-(tert-butoxycarbonyl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl]carbonyl]-4-[(5-chloroindol-2-yl)sulfonyl]-2-(N-methylcarbamoyl)piperazine (40 mg), followed by stirring at room temperature for 1 hour. Diethyl ether was added to the reaction mixture. The precipitate so formed was collected by filtration and washed with diethyl ether. Methylene chloride (7 ml) and triethylamine (81 μl) were added, followed by the addition of acetic acid (34 μl). To the resulting mixture were added a 30% aqueous solution (21 μl) of formaldehyde and sodium triacetoxyborohydride (64 mg), followed by stirring at room temperature for 30 minutes. The solvent was distilled off under reduced pressure. Methylene chloride was added and the resulting mixture was washed with water and saturated aqueous NaCl solution. The organic layer was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was dissolved in a 1N ethanol hydrochloride solution. After stirring at room temperature for 5 minutes, the solvent was distilled off under reduced pressure. The precipitate so formed was collected by filtration and washed with diethyl ether, whereby the title compound (68 mg) was obtained as a white solid.

Workup

  1. customThe precipitate so formed
  2. filtrationwas collected by filtration
  3. washwashed with diethyl ether
  4. additionMethylene chloride (7 ml) and triethylamine (81 μl) were added
  5. additionfollowed by the addition of acetic acid (34 μl)
  6. additionTo the resulting mixture were added a 30% aqueous solution (21 μl) of formaldehyde and sodium triacetoxyborohydride (64 mg)
  7. stirringby stirring at room temperature for 30 minutes
  8. distillationThe solvent was distilled off under reduced pressure
  9. additionMethylene chloride was added
  10. washthe resulting mixture was washed with water and saturated aqueous NaCl solution
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. distillationdistilled under reduced pressure
  13. customto remove the solvent
  14. dissolutionThe residue was dissolved in a 1N ethanol hydrochloride solution
  15. stirringAfter stirring at room temperature for 5 minutes
  16. distillationthe solvent was distilled off under reduced pressure
  17. customThe precipitate so formed
  18. filtrationwas collected by filtration
  19. washwashed with diethyl ether, whereby the title compound (68 mg)
  20. customwas obtained as a white solid

Sources & evidence

ORD record
ord-52a27ec2326746b5aeff76914c79b11d
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

Loading…