Hydrochloric Acid → HCID 57585037, compound

HRID 2077620Notes

Reaction equation

HRID 2077620 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:11]3[N:12]=[CH:13][S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[O:17]COCCOC.Cl>>[S:14]1[C:10]2[CH:9]=[C:8]([C:5]3[CH:4]=[C:3]([OH:17])[C:2]([Cl:1])=[N:7][CH:6]=3)[CH:16]=[CH:15][C:11]=2[N:12]=[CH:13]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 86628004HCID 86628004, compound

Product 1

HCID 57585037HCID 57585037, compoundYield 92%

Procedure

A 5 mL conical microwave vessel was charged with 6-(6-chloro-5-((2-methoxyethoxy)methoxy)pyridin-3-yl)benzo[d]thiazole (0.0231 g, 0.0658 mmol), 2 mL TFE, 2M HCl (0.0329 ml, 0.0658 mmol), and a stirbar. The vessel was flushed with nitrogen, and then sealed. The reaction was irradiated using a Biotage microwave synthesizer to 100° C. for 15 minutes, and cooled. The solution was concentrated to half volume under a stream of nitrogen, and diluted with 1 mL 10% aqueous EtOH. The slurry was stirred at room temperature overnight, and cooled to −5° C. in a refrigerator. The precipitate was collected using a glass frit with a 0.22 μm PTFE syringe filter attached and positive pressure nitrogen. The solids were washed with 1 mL 10% aqueous EtOH, and then dried under a stream of nitrogen for 2 h. The solids were dissolved in DMF (2×2 mL), and filtered through the PTFE membrane. The solvent was removed in vacuo to afford 5-(benzo[d]thiazol-6-yl)-2-chloropyridin-3-ol (0.0159 g, 91.9% yield). 1H NMR (400 MHz, DMF) δ ppm 7.77 (d, J=2.13 Hz, 1H) 7.90 (dd, J=8.53, 1.76 Hz, 1H) 8.22 (d, J=8.41 Hz, 1H) 8.35 (d, J=2.13 Hz, 1H) 8.60 (d, J=1.00 Hz, 1H) 9.52 (s, 1H) 11.20 (s, 1H). 13C NMR (101 MHz, DMF) δ ppm 121.32 (s, 1 C) 122.52 (s, 1 C) 123.86 (s, 1 C) 125.82 (s, 1 C) 134.31 (s, 1 C) 135.34 (s, 1 C) 136.79 (s, 1 C) 138.14 (s, 1 C) 138.21 (s, 1 C) 150.44 (s, 1 C) 153.79 (s, 1 C) 157.01 (s, 1 C). HPLC-MS: 1.63 min (98.5%@215 nm; 97.9% @254 nm; m/z=262.9, calculated for C12H7ClN2OS+H+=263.0).

Workup

  1. customThe vessel was flushed with nitrogen
  2. customsealed
  3. customThe reaction was irradiated
  4. customto 100° C.
  5. customfor 15 minutes
  6. temperaturecooled
  7. concentrationThe solution was concentrated to half volume under a stream of nitrogen
  8. additiondiluted with 1 mL 10% aqueous EtOH
  9. temperaturecooled to −5° C. in a refrigerator
  10. customThe precipitate was collected
  11. filtrationfilter
  12. washThe solids were washed with 1 mL 10% aqueous EtOH
  13. customdried under a stream of nitrogen for 2 h
  14. dissolutionThe solids were dissolved in DMF (2×2 mL)
  15. filtrationfiltered through the PTFE membrane
  16. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f451cf6c415c47ba902bf0c1d1b685b6
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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