HCID 178458275, compound → HCID 178434971, compound

HRID 14406Notes

Reaction equation

[CH2:1]([N:4]([CH2:12][C:13]([NH:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([CH2:23][NH:24]/[C:25](=[N:34]/[C:35]([C:37]2[C:38]([C:43]3[CH:48]=[CH:47][C:46]([O:49][CH2:50][CH:51]=C)=[CH:45][CH:44]=3)=[N:39][O:40][C:41]=2[CH3:42])=[O:36])/[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:18][C:17]=1[Cl:53])=[O:14])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=C>ClCCCl.Cl[Ru](=C1N(C2C(C)=CC(C)=CC=2C)CCN1C1C(C)=CC(C)=CC=1C)(Cl)(=CC1C=CC=CC=1)[P](C1CCCCC1)(C1CCCCC1)C1CCCCC1>[C:30]([O:29][C:27]([NH:26][C:25]1[NH:24][CH2:23][C:19]2[CH:18]=[C:17]([Cl:53])[C:16](=[C:21]([Cl:22])[CH:20]=2)[NH:15][C:13](=[O:14])[CH2:12][N:4]([C:5]([O:6][C:7]([CH3:8])([CH3:10])[CH3:9])=[O:11])[CH2:1][CH:2]=[CH:51][CH2:50][O:49][C:46]2[CH:45]=[CH:44][C:43](=[CH:48][CH:47]=2)[C:38]2[C:37](=[C:41]([CH3:42])[O:40][N:39]=2)[C:35](=[O:36])[N:34]=1)=[O:28])([CH3:31])([CH3:32])[CH3:33]

Participants

Conditions

Temperature: 45 °C

Procedure

The intermediate (170 mg, 0.216 mmol) from Step 1(B) was dissolved in 35 mL of 1,2-dichloroethane, followed by the addition of Grubbs Catalyst 2nd Generation (40 mg, 0.047 mmol) with 2 mL of 1,2-dichloroethane. The resulted reaction mixture was stirred at 45° C. for 2 hrs. Solvent was evaporated in vacuo to give a crude product, which was purified by flash chromatography (15% EtOAc/DCM, Rf 0.37) to give 85 mg (53%, theoretical yield 161 mg).

Workup

customThe resulted reaction mixture
customSolvent was evaporated in vacuo

Sources & evidence

ORD record: ord-1c50ab84cb2c4823992177ebc74ebb1a
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07732434B2

Reaction notes

Loading…