Hydrochloric Acid → HCID 178478767, compound

HRID 552977Notes

Reaction equation

HRID 552977 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].[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][CH2:3][CH2:2]1

Participants

6

Reactant 3

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

Product 1

HCID 178478767HCID 178478767, 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 (193.5 mg), the salt was dissolved in ethanol. Treated 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 (5-10% 2M ammonia in methanol, 95-90% dichloromethane). The resulting yellow oil was found to be the desired product, compound 154, by 1H-NMR. 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 solid, compound 155. Yield: 116 mg of yellow solid. 1H-NMR (DMSO-d6) δ 7.73-7.72 (d, J=3.6 Hz, 1H), 7.60-7.59 (d, J=4.5, 1H), 7.46-7.43 (d, J=8.1 Hz, 1H), 7.21-7.20 (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 (193.5 mg)
  3. dissolutionthe salt was dissolved in ethanol
  4. additionTreated amberlite resin (3.00 g)
  5. additionwas added to the solution
  6. additionThe reaction was diluted with ethyl acetate (30 mL)
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customto afford a yellow oil
  10. customThe material was absorbed onto silica gel
  11. custompurified by silica gel column chromatography (5-10% 2M ammonia in methanol, 95-90% dichloromethane)
  12. dissolutionThe oil was dissolved in anhydrous dichloromethane (5 mL)
  13. custompurged
  14. customreaction vial
  15. stirringThe reaction was stirred for 10 minutes
  16. filtrationfiltered
  17. washThe vial and the filter were washed with ethyl acetate
  18. customThe yellow-brown oil which remained in the reaction
  19. additionthe solution poured through the filter
  20. washThe filter was washed with methanol
  21. concentrationconcentrated
  22. customto afford a yellow oil
  23. customAdditional drying under high vacuum

Sources & evidence

ORD record
ord-f505dc754401462793f97b152a206846
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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