HCID 59327250, compound → HCID 59326869, compound

HRID 1880060Notes

Reaction equation

HRID 1880060 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:25]3[CH2:26][CH2:27][O:28][CH2:29][CH:30]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]>C1COCC1.[OH-].[Pd+2].[OH-]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:12]1[CH:13]=[CH:14][C:15]([O:18][C:19]2[C:24]([C:25]3[CH2:26][CH2:27][O:28][CH2:29][CH:30]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:16][CH:17]=1)[OH:11]

Participants

4

Reactant 1

HCID 59327250HCID 59327250, compound

Product 1

HCID 59326869HCID 59326869, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a round bottomed flask was added benzo[d]thiazol-2-yl(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanone (0.6000 g, 1.448 mmol) in THF (4.83 mL). Palladium hydroxide (0.051 g, 0.072 mmol) was added. The round bottomed flask was flushed with N2(g) followed by vacuum repeating the process three times. A balloon of H2(g) was then added to the reaction. Reaction was filtered through celite. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Synergi column, 4 micron, MAX-RP, 80 Å, 150×30 mM, 0.1% TFA in ACN/H2O, gradient 50% to 100% over 15 min to provide benzo[d]thiazol-2-yl(4-(3-(3,6-dihydro-2H-pyran-4-yl)pyridin-2-yloxy)phenyl)methanol. MS (ESI, pos. ion) m/z: 416.9 (M+1). IC50 (uM) +++.

Workup

  1. customThe round bottomed flask was flushed with N2(g)
  2. additionA balloon of H2(g) was then added to the reaction
  3. customReaction
  4. filtrationwas filtered through celite
  5. customThe crude product was purified by reverse-phase preparative HPLC
  6. customover 15 min

Sources & evidence

ORD record
ord-1f0f08084ccb42458d7d33f9943dc4a2
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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