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 1786117Notes

Reaction equation

HRID 1786117 reaction equation
[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

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 2

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-660ffe71a09d47239b277df2fbed2325
Source dataset
uspto-grants-2009_03
Patent number
US07507726B2

Reaction notes

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