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

HRID 493594

反応式

HRID 493594 の反応式
[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

参加物

10

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 6

HCID 30318Osmium Tetroxide触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 24437Sodium Sulfite溶媒HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-d81ce178e9dc4219a85a0bf224d3793b
出典データセット
uspto-grants-2009_05
特許番号
US07534784B2

関連ノート

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