Hydrochloric Acid → 2,6-Dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

HRID 1177469Notes

Reaction equation

HRID 1177469 reaction equation
[O:1]1CCCO[CH:2]1[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2[S:15][C:16]3[C:21]([N:22]=2)=[CH:20][CH:19]=[C:18]([C:23]2([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:25][CH2:24]2)[N:17]=3)=[CH:9][C:8]=1[CH3:32].Cl.[OH-].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.CCOC(C)=O.O>[CH3:13][C:12]1[CH:11]=[C:10]([C:14]2[S:15][C:16]3[C:21]([N:22]=2)=[CH:20][CH:19]=[C:18]([C:23]2([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:25][CH2:24]2)[N:17]=3)[CH:9]=[C:8]([CH3:32])[C:7]=1[CH:2]=[O:1]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 671115052-(4-(1,3-Dioxan-2-yl)-3,5-dimethylphenyl)-5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine

Product 1

HCID 866387112,6-Dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(4-(1,3-dioxan-2-yl)-3,5-dimethylphenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine (96.0 mg, 0.217 mmol) and hydrochloric acid (5.0M, aq; 1.5 mL, 7.50 mmol) in THF (3.0 mL) was heated at 60° C. in a sealed flask under argon. After 2 h, the reaction was allowed to cool to 25° C. The resulting mixture was diluted with EtOAc (50 mL) and water (20 mL), neutralized with 5.0N NaOH (1.5 mL), and saturated aqueous sodium bicarbonate (10 mL) was added. The organic layer was then separated, sequentially washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2,6-dimethyl-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-benzaldehyde as a yellow-orange solid. MS (ESI) m/z: Calculated: 384.1; Observed: 385.1 (M++1).

Workup

  1. temperatureto cool to 25° C
  2. additionwas added
  3. customThe organic layer was then separated
  4. washsequentially washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01365dbb3f6749fe8c37980ffbf6cf67
Source dataset
uspto-grants-2010_11
Patent number
US07842685B2

Reaction notes

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