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 453306Notes

Reaction equation

HRID 453306 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-f9475f7f263e4fee919f75eb38cc1f08
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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