Hydrazine → benzyl 4-(6-oxo-6,7-dihydro-5H-imidazo[4,5-c]pyridazin-5-yl)piperidine-1-carboxylate

HRID 493594

반응식

HRID 493594 반응식
[CH2:1]([CH:4]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[CH2:11][CH2:10]2)[C:7](=[O:25])[NH:6][C:5]1=O)[CH:2]=C.I([O-])(=O)(=O)=O.[Na+].[NH2:33][NH2:34]>C1COCC1.O.[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+].C(O)(=O)C.[Os](=O)(=O)(=O)=O>[O:25]=[C:7]1[NH:6][C:5]2[N:33]=[N:34][CH:2]=[CH:1][C:4]=2[N:8]1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH2:11][CH2:10]1

참가 물질

10

반응물 3

HCID 9321HydrazineHCID 22293269Benzyl 4-(5-allyl-2,4-dioxoimidazolidin-1-yl)piperidine-1-carboxylateHCID 23667635Sodium periodate

생성물 1

HCID 22293218benzyl 4-(6-oxo-6,7-dihydro-5H-imidazo[4,5-c]pyridazin-5-yl)piperidine-1-carboxylate수율 6.8%

시약·촉매·용매 6

HCID 30318Osmium Tetroxide촉매HCID 176Acetic Acid용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 24437Sodium Sulfite용매HCID 516892Sodium Bicarbonate용매

반응 조건

온도
50 °C

실험 절차

Benzyl 4-(5-allyl-2,4-dioxoimidazolidin-1-yl)piperidine-1-carboxylate (0.480 g, 1.34 mmol) was dissolved in THF (5 mL), and osmium tetroxide (0.05 mL, 2.5% solution in t-butanol) was added followed by a solution of sodium periodate (0.862 g, 4.03 mmol) in water (4 mL). After 24 h, the reaction was diluted with saturated aqueous Na2SO3 and NaHCO3 and extracted with ethyl acetate (4×). The combined organic washes were dried over sodium sulfate, filtered and evaporated to give the crude aldehyde (0.352 g). To a portion of this material (0.250 g, 0.696 mmol) in acetic acid (10 mL) was added hydrazine (0.446 mL, 13.9 mmol). This mixture was heated at 50° C. for 24 h, and then concentrated to dryness. Purification by reverse phase HPLC (C-18, 95% water/acetonitrile →5% water/acetonitrile with 0.1% trifluoroacetic acid) gave the product (0.032 g). MS 354.2 (M+1).

후처리

  1. extractionextracted with ethyl acetate (4×)
  2. dry with materialThe combined organic washes were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customto give the crude aldehyde (0.352 g)
  6. concentrationconcentrated to dryness
  7. customPurification by reverse phase HPLC (C-18, 95% water/acetonitrile →5% water/acetonitrile with 0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-d81ce178e9dc4219a85a0bf224d3793b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07534784B2

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