Hydrochloric Acid → HCID 57585094, compound

HRID 2077598Notes

Reaction equation

HRID 2077598 reaction equation
COCCOC[O:7][C:8]1[CH:9]=[C:10]([C:18]2[CH:30]=[CH:29][C:21]3[N:22]=[C:23]([NH:25][C:26](=[O:28])[CH3:27])[S:24][C:20]=3[CH:19]=2)[CH:11]=[N:12][C:13]=1[C:14]([F:17])([F:16])[F:15].Cl>>[OH:7][C:8]1[CH:9]=[C:10]([C:18]2[CH:30]=[CH:29][C:21]3[N:22]=[C:23]([NH:25][C:26](=[O:28])[CH3:27])[S:24][C:20]=3[CH:19]=2)[CH:11]=[N:12][C:13]=1[C:14]([F:15])([F:16])[F:17]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 57585005HCID 57585005, compound

Product 1

HCID 57585094HCID 57585094, compoundYield 62.1%

Procedure

A 5 mL, conical microwave vessel was charged with N-(6-(5-((2-methoxyethoxy)methoxy)-6-(trifluoromethyl)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.0137 g, 0.031 mmol), 1M HCl (0.093 ml, 0.093 mmol) and 1.5 mL TFE. The vessel was flushed with nitrogen, sealed, and irradiated to 100° C. using a Biotage initiator microwave for 10 minutes. The solution was concentrated in vacuo, and dried at <1.0 mm Hg for 1 h. The residue was treated with 0.5 mL EtOH, briefly sonicated, and set at room temperature for 1 h. The solids were collected using a 0.22 μm PTFE filter under positive pressure nitrogen, and washed with 0.5 mL EtOH. The precipitate was heated into 2 mL TFE, filtered through a 0.22 μm PTFE filter, and concentrated in vacuo. The solids were then dried at 60° C. and <0.5 mm Hg for 1 h to afford N-(6-(5-hydroxy-6-(trifluoromethyl)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.0068 g, 62% yield). 1H NMR (400 MHz, THF) δ ppm 2.22 (s, 3H) 7.53 (d, J=1.37 Hz, 1H) 7.68 (dd, J=8.46, 1.91 Hz, 1H) 7.77 (dd, J=8.41, 0.49 Hz, 1H) 8.18 (d, J=1.76 Hz, 1H) 8.47 (d, J=1.66 Hz, 1H) 9.68 (br. s., 1H) 11.36 (br. s., 1H). 19F NMR (377 MHz, THF) δ ppm −65.58 (s, 3 F). HPLC-MS: retention time=1.78 min (97.7%@215 nm; 97.8% @254 nm; m/z=354.0, calculated for C15H10F3N3O2S+H+=354.0).

Workup

  1. customThe vessel was flushed with nitrogen
  2. customsealed
  3. customirradiated to 100° C.
  4. customfor 10 minutes
  5. concentrationThe solution was concentrated in vacuo
  6. customdried at <1.0 mm Hg for 1 h
  7. additionThe residue was treated with 0.5 mL EtOH
  8. custombriefly sonicated
  9. customThe solids were collected
  10. filtrationfilter under positive pressure nitrogen
  11. washwashed with 0.5 mL EtOH
  12. temperatureThe precipitate was heated into 2 mL TFE
  13. filtrationfiltered through a 0.22 μm PTFE
  14. filtrationfilter
  15. concentrationconcentrated in vacuo
  16. customThe solids were then dried at 60° C.

Sources & evidence

ORD record
ord-e77b9140398f49e0939bdf5236eaeb66
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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