N-[(2R)-2-({2-[4-(3-Buten-1-yl)-6-(dimethylamino)-1,3,5-triazin-2-yl]hydrazino}carbonyl)-7-octen-1-yl]-N-benzoxyformamide → N-{[(5R)-16-(Dimethylamino)-4-oxo-2,3,15,17,18-pentaazabicyclo[12.3.1]octadeca-1(18),10,14,16-tetraen-5-yl]methyl}-N-benzoxyformamide

HRID 1786117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786117
[CH2:1]([C:5]1[N:10]=[C:9]([N:11]([CH3:13])[CH3:12])[N:8]=[C:7]([NH:14][NH:15][C:16]([C@H:18]([CH2:31][CH2:32][CH2:33][CH2:34]C=C)[CH2:19][N:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[O:22])=[O:17])[N:6]=1)[CH2:2][CH:3]=[CH2:4]>ClCCl.CC1C=C(C)C(N2[CH-]N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC([PH+](C2CCCCC2)C2CCCCC2)CC1.C1C=CC(C=[Ru](Cl)Cl)=CC=1>[CH3:12][N:11]([CH3:13])[C:9]1[N:10]=[C:5]2[N:6]=[C:7]([N:8]=1)[NH:14][NH:15][C:16](=[O:17])[C@@H:18]([CH2:19][N:20]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:21]=[O:22])[CH2:31][CH2:32][CH2:33][CH2:34][CH:4]=[CH:3][CH2:2][CH2:1]2

Komponenten

4

Edukt 1

HCID 86621283N-[(2R)-2-({2-[4-(3-Buten-1-yl)-6-(dimethylamino)-1,3,5-triazin-2-yl]hydrazino}carbonyl)-7-octen-1-yl]-N-benzoxyformamide

Produkt 1

HCID 86621284N-{[(5R)-16-(Dimethylamino)-4-oxo-2,3,15,17,18-pentaazabicyclo[12.3.1]octadeca-1(18),10,14,16-tetraen-5-yl]methyl}-N-benzoxyformamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 12045765Benzylidene(dichloro)(1,3-dimesitylimidazolidin-2-id-2-yl)(tricyclohexylphosphoranyl)rutheniumKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of N-[(2R)-2-({2-[4-(3-buten-1-yl)-6-(dimethylamino)-1,3,5-triazin-2-yl]hydrazino}carbonyl)-7-octen-1-yl]-N-benzoxyformamide (280 mg, 0.566 mmol) in dichloromethane (225 mL, 0.0025M) at room temperature was added tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydro-imidazol-2-ylidene][benzylidene]ruthenium(IV) dichloride (2nd generation Grubbs catalyst, 48 mg, 0.057 mmol). The reaction mixture was stirred and heated to reflux for 48 hours, the solvent was evaporated in vacuo, and the residue was then purified by HPLC to afford the title compound as a white solid. MH+468.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 48 hours
  3. customthe solvent was evaporated in vacuo
  4. customthe residue was then purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-660ffe71a09d47239b277df2fbed2325
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507726B2

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