Triethylamine → 1-(2-Azidopropyl)-8-(1-ethoxyethoxy)-1,7,8,9-tetrahydro-pyrano[2,3-g]indazole

HRID 2121879노트

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HRID 2121879 반응식
[CH2:1]([O:3][CH:4]([O:6][CH:7]1[CH2:23][O:22][C:10]2=[CH:11][CH:12]=[C:13]3[C:17]([N:16]([CH2:18][CH:19](O)[CH3:20])[N:15]=[CH:14]3)=[C:9]2[CH2:8]1)[CH3:5])[CH3:2].C(N(CC)CC)C.CS(OS(C)(=O)=O)(=O)=O.[N-:40]=[N+:41]=[N-:42].[Na+]>C1COCC1.CS(C)=O>[N:40]([CH:19]([CH3:20])[CH2:18][N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]3[O:22][CH2:23][CH:7]([O:6][CH:4]([O:3][CH2:1][CH3:2])[CH3:5])[CH2:8][C:9]3=2)[CH:14]=[N:15]1)=[N+:41]=[N-:42]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 33557Sodium AzideHCID 81560Methanesulfonic anhydrideHCID 22496588HCID 22496588, 화합물

생성물 1

HCID 224966011-(2-Azidopropyl)-8-(1-ethoxyethoxy)-1,7,8,9-tetrahydro-pyrano[2,3-g]indazole수율 72.4%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매

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온도
90 °C

실험 절차

To solution of the product from Step G (0.52 g, 1.6 mmol) and triethylamine (1.12 mL, 8.1 mmol) in anhydrous THF (75 ml) at 0° C. was added methanesulfonic anhydride (0.71 g, 4.05 mmol). The mixture was stirred for 20 min and sodium azide (2.11 g, 32.4 mmol) was added along with DMSO (20 mL). The THF was removed (in vacuo) and the reaction mixture was heated at 90° C. for 3 h. The mixture was cooled, poured into a saturated solution of sodium bicarbonate (150 mL), and extracted with EtOAc (3×100 mL). The combined extracts were washed with brine (100 mL), dried (MgSO4), and evaporated to a residue that was purified by chromatography (silica, 10% EtOAc/hexane) to give an oil (0.40 g, 72%): LC/MS (+APCI) mz 346 (M+H).

후처리

  1. customThe THF was removed (in vacuo)
  2. temperatureThe mixture was cooled
  3. additionpoured into a saturated solution of sodium bicarbonate (150 mL)
  4. extractionextracted with EtOAc (3×100 mL)
  5. washThe combined extracts were washed with brine (100 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated to a residue that
  8. customwas purified by chromatography (silica, 10% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-6e9c41cacb824331b92492865ec513e4
출처 데이터셋
uspto-grants-2004_02
특허 번호
US06696476B2

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