Hydrogen Peroxide → 2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carboxylic acid amide

HRID 1773929노트

반응식

HRID 1773929 반응식
[I:1][C:2]1[N:11]=[C:10]2[N:4]([CH2:5][CH2:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH:9]2[O:12][CH:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)[C:3]=1[C:24]#[N:25].[OH-].[Na+].OO.[O-:30]S([O-])(=S)=O.[Na+].[Na+]>CO>[I:1][C:2]1[N:11]=[C:10]2[N:4]([CH2:5][CH2:6][C:7]3[CH:23]=[CH:22][CH:21]=[CH:20][C:8]=3[CH:9]2[O:12][CH:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]2)[C:3]=1[C:24]([NH2:25])=[O:30]

참가 물질

6

반응물 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 24477Sodium ThiosulfateHCID 867039962-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carbonitrile

생성물 1

HCID 867040192-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carboxylic acid amide

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carbonitrile (example 221A) (220 mg, 0.5 mmole) in MeOH (3 mL) cooled at 0° C. is added dropwise a solution of 1N NaOH (1 mL) and 30% H2O2 (0.1 mL). The reaction mixture is stirred at 0° C. for 1 hour, then aqueous 1N Na2S2O3 is added. The aqueous phase is extracted with AcOEt. The organic phase is dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH:NH4OH) from (100:0:0) to (90:10:1) to give 2-iodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-1-carboxylic acid amide melting at 85° C.

후처리

  1. extractionThe aqueous phase is extracted with AcOEt
  2. dry with materialThe organic phase is dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with (CH2Cl2:MeOH:NH4OH) from (100:0:0) to (90:10:1)

출처 및 근거

ORD 기록
ord-22a8d85962de4afa9514308c836385c0
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255101B2

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