3-Azabicyclo[3.2.2]nonane → HCID 86628000, compound

HRID 2077595Notes

Reaction equation

HRID 2077595 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15]C(=O)C)[S:14][C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1.[CH:21]12[CH2:29][CH2:28][CH:25]([CH2:26][CH2:27]1)[CH2:24][NH:23][CH2:22]2>>[CH:21]12[CH2:29][CH2:28][CH:25]([CH2:26][CH2:27]1)[CH2:24][N:23]([C:2]1[N:7]=[C:6]([C:8]3[CH:20]=[CH:19][C:11]4[N:12]=[C:13]([NH2:15])[S:14][C:10]=4[CH:9]=3)[CH:5]=[N:4][CH:3]=1)[CH2:22]2

Participants

3

Reactant 2

HCID 92403-Azabicyclo[3.2.2]nonaneHCID 51354316HCID 51354316, compound

Product 1

HCID 86628000HCID 86628000, compoundYield 24.6%

Conditions

Temperature
140 °C

Procedure

A 10 mL, CEM microwave vial was charged with N-(6-(6-chloropyrazin-2-yl)benzo[d]thiazol-2-yl)acetamide (0.0657 g, 0.22 mmol), 3-aza-bicyclo[3.2.2]nonane (0.032 g, 0.26 mmol), 1 mL dry TFE and a stirbar. The vessel was flushed with Ar, sealed and heated using a 110° C. heat block for 12 h. The reaction was cooled and 4 mL EtOH was added. The vial was sealed and the slurry was heated to 140° C. using a heat transfer block for 5 minutes and cooled. The slurry was filtered using a course glass filter fitted with a 0.22 μm teflon filter. The solid was dried at 60° C. and <1 mm Hg for 3 h and then dissolved in warm DMF. The turbid solution was filtered through a 0.22 μm teflon filter, and the solvent was removed in vacuo to afford 6-(6-(3-aza-bicyclo[3.2.2]nonan-3-yl)pyrazin-2-yl)benzo[d]thiazol-2-amine (19 mg). 1H NMR (400 MHz, Pyr) δ ppm 1.48-1.68 (m, 8H) 2.01 (s, 2H) 3.83 (d, J=4.11 Hz, 4H) 7.92 (dd, J=8.41, 0.39 Hz, 1H) 8.28 (dd, J=8.41, 1.86 Hz, 1H) 8.34 (s, 1H) 8.71 (s, 1H) 8.75 (dd, J=1.37, 0.49 Hz, 1H) 8.89 (s, 2H). 13C NMR (101 MHz, Pyr) δ ppm 25.05 (s, 4 C) 30.68 (s, 2 C) 53.39 (s, 2 C) 118.92 (s, 1 C) 119.97 (s, 1 C) 125.11 (s, 1 C) 128.54 (s, 1 C) 128.71 (s, 1 C) 131.27 (s, 1 C) 133.33 (s, 1 C) 149.01 (s, 1 C) 155.03 (s, 1 C) 155.42 (s, 1 C) 169.00 (s, 1 C).

Workup

  1. customdry TFE
  2. customThe vessel was flushed with Ar
  3. customsealed
  4. temperatureheated
  5. customusing a 110° C.
  6. temperatureheat block for 12 h
  7. temperatureThe reaction was cooled
  8. addition4 mL EtOH was added
  9. customThe vial was sealed
  10. customfor 5 minutes
  11. temperaturecooled
  12. filtrationThe slurry was filtered
  13. filtrationfilter
  14. customfitted with a 0.22 μm teflon
  15. filtrationfilter
  16. customThe solid was dried at 60° C.
  17. dissolutiondissolved in warm DMF
  18. filtrationThe turbid solution was filtered through a 0.22 μm teflon
  19. filtrationfilter
  20. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0de91ee4a1af47148ad9edba513ea22d
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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