5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide → 5-(3-oxopropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

HRID 1799120Notes

Reaction equation

HRID 1799120 reaction equation
[O:1]1CCO[CH:2]1[CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[S:29][C:30]2[C:35]([N:36]=1)=[CH:34][CH:33]=[CH:32][N:31]=2)=[O:20]>C1COCC1.CC(O)=O.O>[O:1]=[CH:2][CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]([NH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]1[S:29][C:30]2[C:35]([N:36]=1)=[CH:34][CH:33]=[CH:32][N:31]=2)=[O:20]

Participants

5

Reactant 1

HCID 585519015-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide

Product 1

HCID 585518735-(3-oxopropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamideYield 87%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (250 mg, 0.5 mmol) was dissolved in a mixture of THF (4 mL), AcOH (8 mL) and H2O (0.5 mL), heated at reflux for 16 h, then concentrated to dryness. The residue was dissolved in EtOAc, washed with sat aq NaHCO3, dried (MgSO4), and concentrated under reduced pressure. The crude product was purified by MPLC eluting with CH2Cl2/MeOH (0-5% gradient) to give 5-(3-oxopropyl)-2-phenyl-N-(2-(thiazolo[5,4-b]pyridin-2-yl)phenyl)thiazole-4-carboxamide (200 mg, 87% yield).

Workup

  1. temperatureheated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated to dryness
  4. dissolutionThe residue was dissolved in EtOAc
  5. washwashed with sat aq NaHCO3
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by MPLC
  9. washeluting with CH2Cl2/MeOH (0-5% gradient)

Sources & evidence

ORD record
ord-e01719da15b4439fb8ddea51fe944c59
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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