Acetic Acid → HCID 57501772, compound

HRID 601536Notes

Reaction equation

HRID 601536 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:34])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH:25](OCC)[O:26]CC)=[C:19]([O:32][CH3:33])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1.C(O)(=O)C>C1COCC1.O.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]3[C:11](=[O:34])[N:12]([C:17]4[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH:25]=[O:26])=[C:19]([O:32][CH3:33])[CH:18]=4)[CH:13]=[CH:14][C:15]=3[N:16]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 57501771HCID 57501771, compound

Product 1

HCID 57501772HCID 57501772, compoundYield 61.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

Dissolve 2-(4-chloro-phenyl)-5-[4-(3,3-diethoxy-propyl)-3-methoxy-phenyl]-5H-thiazolo[5,4-c]pyridin-4-one (180 mg, 0.36 mmol) in THF (2.0 mL) and water (1.0 mL) then add glacial acetic acid (0.6 mL). Stir the solution at 45° C. overnight. Dilute the solution with EtOAc (50 mL), wash with saturated NaHCO3 (20 mL), then dry, filter and concentrate the solution. Purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 80% EtOAc/hexanes, to give the title compound (94 mg, 61%). MS (ES+) 425.0 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 9.83 (s, 1H), 8.03 (d, 2H, J=8.3 Hz), 7.49 (d, 2H, J=8.8 Hz), 7.41 (d, 1H, J=7.5 Hz), 7.26 (m, 1H), 6.99-6.89 (m, 3H), 3.84 (s, 3H), 2.99 (t, 2H, J=7.3 Hz), 2.77 (t, 2H, J=7.3 Hz).

Workup

  1. washwash with saturated NaHCO3 (20 mL)
  2. customdry
  3. filtrationfilter
  4. concentrationconcentrate the solution
  5. customPurify the crude material by flash chromatography

Sources & evidence

ORD record
ord-b215efe872c84d2bba1719a2fd3b6288
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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