Hydrochloric Acid → HCID 59385209, compound

HRID 2356810Notes

Reaction equation

HRID 2356810 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[C:10]([Cl:18])[CH:9]=2)=[CH:4][CH:3]=1.Cl[C:20]1[S:21][C:22]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:23]=2[N:24]=1.Cl.O1CCOCC1>C(O)CCC>[F:29][C:27]1[CH:26]=[CH:25][C:23]2[N:24]=[C:20]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([C:8]4[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[C:10]([Cl:18])[CH:9]=4)=[CH:6][CH:7]=3)[S:21][C:22]=2[CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 20498702-Chloro-6-fluorobenzothiazoleHCID 59385318HCID 59385318, compound

Product 1

HCID 59385209HCID 59385209, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of methyl 4′-amino-3-chlorobiphenyl-4-carboxylate (0.45 g, 1.7 mmol) and 2-chloro-6-fluoro-1,3-benzothiazole (0.32 g, 1.7 mmol) in n-butanol (8 mL) was heated to 60-70° C., and then 4N HCl in 1,4-dioxane (0.19 mL, 0.77 mmol) was added dropwise with stirring. The reaction mixture was heated at 90° C. for 18 h. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure. The residue was triturated with ethanol, and the solid was collected by filtration. This yielded 0.399 g (56%) of the title compound as a beige solid. LC/MS m/z 411 (MH+), retention time 4.03 min. 1H NMR (400 MHz, DMSO-d6) δ 3.85 (s, 3H), 7.12 (t, 1H), 7.67-7.87 (m, 9H), 10.62 (br, 1H).

Workup

  1. temperatureThe reaction mixture was heated at 90° C. for 18 h
  2. temperatureUpon cooling to rt
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customThe residue was triturated with ethanol
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-06cb252c89e64f378dfbd54ea5666aad
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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