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

HRID 2060632ノート

反応式

HRID 2060632 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 313Hydrochloric Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a9a3fb1173344194995455918e56a668
出典データセット
uspto-grants-2012_10
特許番号
US08278335B2

反応ノート

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