Hydrochloric Acid → HCID 57584917, compound

HRID 2077597Notes

Reaction equation

HRID 2077597 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[O:21]COCCOC.Cl>>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:20]=[CH:19][C:11]3[N:12]=[C:13]([NH:15][C:16](=[O:18])[CH3:17])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[OH:21]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 57585046HCID 57585046, compound

Product 1

HCID 57584917HCID 57584917, compoundYield 104.2%

Procedure

A dry 10 mL, round bottom flask was charged with N-(6-(6-chloro-5-((2-methoxyethoxy)methoxy)pyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.0050 g, 0.012 mmol), a stirbar, and 1 mL dry TFE. To the stirring solution was added a 1 M solution of hydrochloric acid (0.037 ml, 0.037 mmol). The solution was transferred to a 5 mL, conical vial, purged with Ar, and sealed. The solution was irradiated using a Biotage microwave synthesizer for 5 minutes at 100° C. The cooled solution was concentrated in vacuo, and sonicated in 0.5 mL THF. The precipitate was collected using a glass frit under positive pressure nitrogen. The solids were washed with 0.5 mL dry THF, initially dried using a stream of nitrogen, and then at 60° C. and <1.0 mm Hg for 30 minutes to afford N-(6-(6-chloro-5-hydroxypyridin-3-yl)benzo[d]thiazol-2-yl)acetamide (0.0040 g). 1H NMR (400 MHz, DMF) 5 ppm 2.33 (s, 3H) 7.77 (dd, J=8.41, 1.86 Hz, 1H) 7.82 (d, J=2.25 Hz, 1H) 7.83 (d, J=8.61 Hz, 1H) 8.30 (d, J=2.15 Hz, 1H) 8.38 (d, J=1.76 Hz, 1H) 11.30 (br. s., 1H) 12.43 (br. s., 1H). 13C NMR (101 MHz, DMF) δ ppm 22.67 (s, 1 C) 120.44 (s, 1 C) 121.39 (s, 1 C) 122.26 (s, 1 C) 125.57 (s, 1 C) 132.27 (s, 1 C) 133.46 (s, 1 C) 137.13 (s, 1 C) 137.72 (s, 1 C) 137.88 (s, 1 C) 149.53 (s, 1 C) 150.58 (s, 1 C) 159.48 (s, 1 C) 169.92 (s, 1 C). 91741-17-1 HPLC-MS: retention time=1.56 min (96.0%@215 nm; >99% @254 nm; m/z=319.9, calculated for C14H10ClN3O2S+H+=320.0).

Workup

  1. customa stirbar, and 1 mL dry TFE
  2. customconical vial, purged with Ar
  3. customsealed
  4. customThe solution was irradiated
  5. customfor 5 minutes
  6. customat 100° C
  7. concentrationThe cooled solution was concentrated in vacuo
  8. customsonicated in 0.5 mL THF
  9. customThe precipitate was collected
  10. washThe solids were washed with 0.5 mL dry THF
  11. custominitially dried

Sources & evidence

ORD record
ord-ebe75240f3cb4dcd9ed5cb6b783adea7
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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