Triethylamine → HCID 178427911, compound

HRID 1890790Notes

Reaction equation

HRID 1890790 reaction equation
[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([C:17](=S)[NH:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.F[B-](F)(F)F.C([O+](CC)CC)C.[N:39]#[C:40][NH2:41].C(N(CC)CC)C>ClCCl.O>[Cl:1][C:2]1[C:3]([CH3:26])=[C:4]([S:8]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([C:17](=[N:41][C:40]#[N:39])[NH:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[CH2:12]2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9864CyanamideHCID 2723982Triethyloxonium tetrafluoroborateHCID 87441131HCID 87441131, compound

Product 1

HCID 178427911HCID 178427911, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 34 (200 mg, 0.48 mmol) in dichloromethane (15 mL) was added triethyloxonium tetrafluoroborate (0.96 mL, 0.96 mmol, 1 Min dichloromethane) and the mixture was stirred at room temperature for overnight. The reaction mixture was then heated to 50° C. for 3 more days with continued stirring. The reaction mixture was cooled, concentrated and triturated in ether. The obtained product was dissolved in ethanol (2 mL) and cyanamide (61 mg, 1.4 mmol) and triethylamine (0.2 mL, 1.4 mmol) were added. After stirring, at 80° C. for 16 hours, the reaction mixture was cooled, diluted with water (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash 280™ (SiO2, 0-100% of ethyl acetate in hexanes). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04-1.34 (m, 5H), 1.44-1.91 (m, 9H), 2.60 (s, 3H), 2.60-2.70 (m, 1H), 2.83-2.98 (m, 1H), 3.08 (t, J=11.4 Hz, 1H), 3.64 (t, 3H), 7.47 (t, J=8.3 Hz, 1H), 7.80 (dd, J=8.1, 1.0 Hz, 1H), 7.83-7.89 (m, 1H), 8.31 (d, J=7.5 Hz, 1H); MS (ESI+) m/z 423 (M+H)+. Anal. Calculated for C20H27ClN4O2S: C, 56.79; H, 6.43; N, 13.29. Found: C, 56.42; H, 6.41; N, 12.98.

Workup

  1. temperatureThe reaction mixture was then heated to 50° C. for 3 more days with continued stirring
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customtriturated in ether
  5. dissolutionThe obtained product was dissolved in ethanol (2 mL)
  6. stirringAfter stirring, at 80° C. for 16 hours
  7. temperaturethe reaction mixture was cooled
  8. extractionextracted with ethyl acetate (3×10 mL)
  9. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c3f0ca1eee2949bb892515e91326d062
Source dataset
uspto-grants-2013_08
Patent number
US08507493B2

Reaction notes

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