Triacetoxyperiodinane → HCID 57725531, compound

HRID 1988486Notes

Reaction equation

HRID 1988486 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][OH:26])[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C1COCC1.C(Cl)Cl.C(OCC)(=O)C>[CH:1]1([CH2:7][NH:8][C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([CH:25]=[O:26])[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 57725598HCID 57725598, compound

Product 1

HCID 57725531HCID 57725531, compoundYield 97.4%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of (4-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yloxy)pyridin-2-yl)methanol (30 mg, 0.081 mmol) in 2 ml of THF and 2 ml of DCM was added Dess-Martin Periodinane (38 mg, 0.089 mmol). The reaction mixture was stirred at room temperature for 30 minutes. The crude reaction mixture diluted with ethyl acetate (60 ml), washed with saturated sodium bicarbonate (2×15 ml), brine (1×15 ml), dried with Na2SO4, filter and concentrated in vacuo to give 4-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yloxy)picolinaldehyde as solid (29 mg). ES/MS m/z 386.1 (MH+) as the hydrate (+18).

Workup

  1. customThe crude reaction mixture
  2. washwashed with saturated sodium bicarbonate (2×15 ml), brine (1×15 ml)
  3. dry with materialdried with Na2SO4
  4. filtrationfilter
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46504f244c704d82babef50a4cb70b5a
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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