HCID 68542752, compound → HCID 68542021, compound

HRID 1432094Notes

Reaction equation

HRID 1432094 reaction equation
[CH2:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:27]=[C:28]([O:30][CH3:31])[N:29]=1)[C:9]([NH:11][CH:12]([CH:20]1[CH2:24][CH:23]([CH3:25])[C:22](=[O:26])[O:21]1)[CH2:13][CH:14]([CH3:19])[CH2:15][CH2:16][CH:17]=[CH2:18])=[O:10])[CH2:2]C=C>C(Cl)Cl.CC1C=C(C)C=C(C)C=1N1CCN(C2C(C)=CC(C)=CC=2C)C1=[Ru-2](Cl)(Cl)=CC1C=CC=CC=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[CH3:31][O:30][C:28]1[N:29]=[C:6]2[CH:7]=[C:8]([C:9](=[O:10])[NH:11][CH:12]([CH:20]3[CH2:24][CH:23]([CH3:25])[C:22](=[O:26])[O:21]3)[CH2:13][CH:14]([CH3:19])[CH2:15][CH2:16][CH:17]=[CH:18][CH2:2][CH2:1][NH:5]2)[CH:27]=1

Participants

4

Reactant 1

HCID 68542752HCID 68542752, compound

Product 1

HCID 68542021HCID 68542021, compound

Reagents, catalysts & solvents 2

HCID 178420535HCID 178420535, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 90 mg (0.21 mmol) 2-but-3-enylamino-6-methoxy-N-[3-methyl-1-(4-methyl-5-oxo-tetrahydro-furan-2-yl)-hept-6-enyl]-isonicotinamide in 6 ml DCM is added dropwise over 30 min to a refluxing solution of 3.5 mg tricyclohexylphosphine [1,3-bis(2,4,6-trimethyl-phenyl)-4,5-dihydroimidazol-2-ylidene][benzylidene]ruthenium(IV)dichloride(‘Grubbs second generation catalyst’) in 6 ml DCM and then stirred for 1 h at reflux. LC/MS shows that only little product has been formed, therefore, 7 mg catalyst are added and the mixture stirred for 18 h at reflux. Again, 11 mg catalyst are added and heating continued for 4 h. The reaction mixture is directly chromatographed on silica gel and eluted with DCM/MeOH 98:2 to yield the title compound (mixture of diastereomers) as a greenish foam.

Workup

  1. temperatureat reflux
  2. customhas been formed
  3. stirringthe mixture stirred for 18 h
  4. temperatureat reflux
  5. temperatureheating
  6. waitcontinued for 4 h
  7. customThe reaction mixture is directly chromatographed on silica gel
  8. washeluted with DCM/MeOH 98:2

Sources & evidence

ORD record
ord-fd5ffaccb7b64f11ae669b0c47c905bd
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

Loading…