Hydrochloric Acid → HCID 178463986, compound

HRID 552976Notes

Reaction equation

HRID 552976 reaction equation
[N:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)=[NH:21])[CH:17]=3)[CH:12]=[CH:11]2)[CH2:6][CH2:5]O[CH2:3][CH2:2]1.I.[ClH:28]>CCOCC.CO>[ClH:28].[ClH:28].[CH2:6]([N:1]([CH2:2][CH3:3])[CH2:7][CH2:8][CH2:9][N:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)=[NH:21])[CH:17]=2)[CH:12]=[CH:11]1)[CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24841Hydrogen iodideHCID 178511927HCID 178511927, compound

Product 1

HCID 178463986HCID 178463986, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Reaction performed as described in Example 40, compound 150. Following isolation of the HI salt by precipitation, the salt was dissolved in ethanol. Amberlite resin (3.00 g) was added to the solution, and the mixture stirred at room temperature for 30 minutes. The reaction was diluted with ethyl acetate (30 mL) and filtered. The filtrate was concentrated to afford a yellow oil. The material was absorbed onto silica gel and purified by silica gel column chromatography (5% 2M ammonia in methanol, 95% dichloromethane). The resulting yellow oil was found to be the desired product, compound 152, by 1H-NMR analysis. The oil was dissolved in anhydrous dichloromethane (5 mL) and transferred to an argon purged reaction vial. The solution was treated with 1M hydrochloric acid in ether (3 mL) and the salt oiled out immediately. The reaction was stirred for 10 minutes and filtered. The vial and the filter were washed with ethyl acetate and the filtrate discarded. The yellow-brown oil which remained in the reaction vial was dissolved in methanol and the solution poured through the filter. The filter was washed with methanol and all organics combined and concentrated to afford a yellow oil. Additional drying under high vacuum afforded a yellow oil, compound 153. Yield: 80.1 mg of yellow oil. 1H-NMR (DMSO-d6) δ 7.74-7.73 (d, J=3.3 Hz, 1H), 7.61-7.60 (d, J=4.5, 1H), 7.47-7.44 (d, J=8.1 Hz, 1H), 7.27 (s, NH), 7.22-7.21 (d, J=3 Hz, 1H), 7.11-7.08 (t, J=4.8 Hz, 1H), 6.92 (s, 1H), 6.60-6.57 (dd, J=1.2, 8.4 Hz, 1H), 6.34-6.33 (d, J=3 Hz, 2H), 4.16-4.12 (t, J=6.9 Hz, 2H), 2.46 (s, 4H), 2.36-2.31 (t, J=6.6 Hz, 2H), 1.93-1.83 (quintet, J=6.7 Hz, 2H), 1.67 (s, 4H) MW 353.

Workup

  1. customReaction
  2. customby precipitation
  3. dissolutionthe salt was dissolved in ethanol
  4. additionAmberlite resin (3.00 g) was added to the solution
  5. additionThe reaction was diluted with ethyl acetate (30 mL)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customto afford a yellow oil
  9. customThe material was absorbed onto silica gel
  10. custompurified by silica gel column chromatography (5% 2M ammonia in methanol, 95% dichloromethane)
  11. dissolutionThe oil was dissolved in anhydrous dichloromethane (5 mL)
  12. custompurged
  13. customreaction vial
  14. stirringThe reaction was stirred for 10 minutes
  15. filtrationfiltered
  16. washThe vial and the filter were washed with ethyl acetate
  17. customThe yellow-brown oil which remained in the reaction
  18. additionthe solution poured through the filter
  19. washThe filter was washed with methanol
  20. concentrationconcentrated
  21. customto afford a yellow oil
  22. customAdditional drying under high vacuum

Sources & evidence

ORD record
ord-60ba8b2f45924986852f3c72aa7b9f90
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

Loading…