4-Fluorobenzoic Acid → HCID 10309477, compound

HRID 1582107Notes

Reaction equation

HRID 1582107 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[CH3:44][O:45][C:46]1[C:51]2[N:52]=[C:53]([NH2:55])[S:54][C:50]=2[C:49]([CH:56]2[CH2:61][CH2:60][O:59][CH2:58][CH2:57]2)=[CH:48][CH:47]=1>C1COCC1.O1CCOCC1.CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:55][C:53]2[S:54][C:50]3[C:49]([CH:56]4[CH2:57][CH2:58][O:59][CH2:60][CH2:61]4)=[CH:48][CH:47]=[C:46]([O:45][CH3:44])[C:51]=3[N:52]=2)=[O:8])=[CH:9][CH:10]=1

Participants

9

Reactant 4

HCID 99734-Fluorobenzoic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 220157354-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amine

Product 1

HCID 10309477HCID 10309477, compoundYield 51%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 32 mg (0.23 mmol) 4-fluoro-benzoic acid in 5 ml THF were added 32 mg (0.25 mmol) HATU and 0.043 ml (0.25 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 1 h. A solution of 60 mg (0.23 mmol) 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amine in 5 ml dioxane and 1 ml DMF was then added and stirring continued at room temperature for 16 h. The reaction mixture was then poured into 100 ml water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (ethyl acetate) followed by trituration in hexane afforded 45 mg (51%) 4-fluoro-N-[4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl]-benzamide as a white crystalline solid. ES-MS m/e (%): 387 (M+H+, 100).

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 16 h
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b7be5978c3e4cd5badbee3be400fb15
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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