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

HRID 1177452
Notes
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Reaction equation

HRID 1177452 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine (96.0 mg, 217 μmol) and hydrochloric acid (5.0M, aq; 1.5 mL, 7500 μmol) in THF (3.0 mL) was heated at 60° C. in a sealed flask under argon. After 2 h, the reaction mixture 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 (20 mL) and brine (15 mL), 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 (20 mL) and brine (15 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ef28c68c837e4f3ea6639ad8440838a3
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842685B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes