Ammonia → HCID 178479305, compound

HRID 552981Notes

Reaction equation

HRID 552981 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[NH:12][CH:11]=2)[CH2:3][CH2:2]1.I.[S:21]1[CH:25]=[CH:24][CH:23]=[C:22]1[C:26](SC)=[NH:27].N.[Cl:31]CCl>C(O)C.CO.CCOCC>[ClH:31].[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:26]([C:22]4[S:21][CH:25]=[CH:24][CH:23]=4)=[NH:27])[CH:17]=3)[NH:12][CH:11]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6344Dichloromethane2×HCID 57474486HCID 57474486, compoundHCID 66704664Methyl thiophene-2-carbimidothioate hydroiodide

Product 1

HCID 178479305HCID 178479305, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To an argon purged vial fitted with a magnetic stirbar was charged a solution of 180 (28 mg, 0.108 mmol) in absolute ethanol (3 mL). Methyl thiophene-2-carbimidothioate hydroiodide (62 mg, 0.217 mmol) was added as a yellow solid in one portion. The reaction was stirred at room temperature for 17 hours. The reaction was complete by TLC (10% 2M ammonia in methanol, 90% dichloromethane). The reaction was diluted with ether (15 mL) and the solid which precipitated was collected by vacuum filtration. The precipitate was washed with ether (10 mL). The product was collected by washing the filter with methanol (10 mL) and collecting the filtrate. The filtrate was returned to the reaction vial and DOWEX-66 (3 g) was added. The reaction was stirred for 2 hours. The reaction was filtered and the filtrate concentrated to afford a brown solid. The solid was taken up in dichloromethane (10 mL) and partitioned with saturated sodium bicarbonate (2 mL). The organic phase was treated with brine, dried over magnesium sulfate and filtered. The filtrate was treated with 1M hydrogen chloride in ether (3 mL). After stirring for 1 hours the reaction was concentrated on the rotary evaporator. The resulting yellow solid was dried further on the high vacuum line. Yield: 45 mg of yellow solid, compound 181 (96%). 1H NMR (DMSO) δ 10.91 (br s, 1H), 7.96 (s, 2H), 7.42-7.39 (d, J=8.4 Hz, 2H), 7.36 (s, 1H), 7.29-7.25 (t, J=4.5 Hz, 1H), 7.24 (s, 1H), 6.92-6.89 (d, J=8.7 Hz, 1H), 3.58 (s, 4H), 2.72-2.67 (t J=7.5 Hz, 2H), 2.38 (m, 6H), 1.83-1.78 (m, 2H). MS (ESI+): 369 (MH+, 100%).

Workup

  1. customTo an argon purged vial fitted with a magnetic stirbar
  2. customthe solid which precipitated
  3. filtrationwas collected by vacuum filtration
  4. washThe precipitate was washed with ether (10 mL)
  5. customThe product was collected
  6. washby washing the
  7. filtrationfilter with methanol (10 mL)
  8. customcollecting the filtrate
  9. additionwas added
  10. stirringThe reaction was stirred for 2 hours
  11. filtrationThe reaction was filtered
  12. concentrationthe filtrate concentrated
  13. customto afford a brown solid
  14. custompartitioned with saturated sodium bicarbonate (2 mL)
  15. additionThe organic phase was treated with brine
  16. dry with materialdried over magnesium sulfate
  17. filtrationfiltered
  18. additionThe filtrate was treated with 1M hydrogen chloride in ether (3 mL)
  19. stirringAfter stirring for 1 hours the reaction
  20. concentrationwas concentrated on the rotary evaporator
  21. customThe resulting yellow solid was dried further on the high vacuum line

Sources & evidence

ORD record
ord-78914d1de9234651a768f1925f4623bc
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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