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

HRID 1177452
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HRID 1177452 반응식
[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]
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참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매
HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ef28c68c837e4f3ea6639ad8440838a3
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842685B2

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