Acetic Acid → HCID 58465881, 화합물

HRID 455682노트

반응식

HRID 455682 반응식
CC(C)([O-])C.[K+].[NH2:7][C:8]1([CH2:24][OH:25])[C:21]2[CH:20]=[C:19]([Cl:22])[N:18]=[CH:17][C:16]=2[O:15][C:14]2[C:9]1=[CH:10][C:11]([Br:23])=[CH:12][CH:13]=2.[N+:26](/[CH:29]=[CH:30]/[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)([O-:28])=[O:27].C(O)(=O)C>C1COCC1.[Cl-].[NH4+].O.CCOC(C)=O>[Br:23][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[O:15][C:16]1[CH:17]=[N:18][C:19]([Cl:22])=[CH:20][C:21]=1[C:8]2([CH2:24][O:25][CH:30]([CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)[CH2:29][N+:26]([O-:28])=[O:27])[NH2:7]

참가 물질

9

반응물 4

HCID 176Acetic AcidHCID 11094860132839-80-6HCID 23665647Potassium tert-butoxideHCID 58465926HCID 58465926, 화합물2회

생성물 1

HCID 58465881HCID 58465881, 화합물

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매HCID 25517Ammonium Chloride용매

실험 절차

Potassium t-butoxide (0.517 g, 4.61 mmol) was added in one portion to a solution of (5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)methanol (Intermediate X, 1.5 g, 4.39 mmol) in THF (30 mL) at −78° C. After stirring for 45 minutes, (E)-(2-nitrovinyl)cyclohexane (0.716 g, 4.61 mmol) in THF (15.00 mL) was added slowly via syringe. The reaction was stirred at −78° C. for 20 minutes and was quenched with acetic acid (0.502 mL, 8.78 mmol) at −78° C., diluted with saturated aqueous ammonium chloride, water and EtOAc. After warming to RT, the layers were seperated and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with water, saturated aqueous sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give the crude material. The crude material was purified by silica gel chromatography by eluting with 1:6 to 1:4 EtOAc in hexane, to provide 7-bromo-3-chloro-5-((1-cyclohexyl-2-nitroethoxy)methyl)-5H-chromeno[2,3-c]pyridin-5-amine as a yellow oil. [M+H]+=496.1.

후처리

  1. stirringThe reaction was stirred at −78° C. for 20 minutes
  2. customthe layers were seperated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic extracts were washed with water, saturated aqueous sodium chloride
  5. dry with materialdried over sodium sulfate
  6. filtrationThe solution was filtered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material
  9. customThe crude material was purified by silica gel chromatography
  10. washby eluting with 1:6 to 1:4 EtOAc in hexane

출처 및 근거

ORD 기록
ord-5df1ee26405148ffbdd8bbb297e61310
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497264B2

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