Ethanol → Ethyl 5-amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

HRID 2060632Notes

Reaction equation

HRID 2060632 reaction equation
C(OC([NH:8][C:9]1[S:13][C:12]([C:14]2[CH:15]=[N:16][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:18][CH:19]=2)=[N:11][C:10]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27])=O)(C)(C)C.O1CCOCC1.C(O)C>Cl>[NH2:8][C:9]1[S:13][C:12]([C:14]2[CH:15]=[N:16][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[CH:18][CH:19]=2)=[N:11][C:10]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

5

Reactant 3

HCID 702EthanolHCID 312751,4-DioxaneHCID 67305664Ethyl 5-[(tert-butoxycarbonyl)amino]-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

Product 1

HCID 58335250Ethyl 5-amino-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ethyl 5-[(tert-butoxycarbonyl)amino]-2-(6-morpholin-4-ylpyridin-3-yl)-1,3-thiazole-4-carboxylate (634 mg, 1.46 mmol) was taken up in 4 N HCl in dioxane (7.3 ml, 29.2 mmol) and ethanol (5 ml) and stirred at ambient temperature for 20 hours. The mixture was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted twice with ethyl acetate. Combined organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting residue was purified via flash chromatography (silica, 0-100% ethyl acetate/hexanes) to afford the title compound. LRMS (APCI) calc'd for (C15H19N4O3S) [M+H]+, 335.1; found 335.0.

Workup

  1. customThe mixture was then partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. dry with materialCombined organics were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified via flash chromatography (silica, 0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a9a3fb1173344194995455918e56a668
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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