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

HRID 2060632노트

반응식

HRID 2060632 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a9a3fb1173344194995455918e56a668
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08278335B2

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