1-({2-(Hex-5-enyl-methyl-carbamoyl)-4-[2-(3-isopropyl-pyrazol-1-yl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-cyclopentanecarbonyl}-amino)-2-vinyl-cyclopropane-carboxylic acid ethyl ester → HCID 68688284, compound

HRID 1443495Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[C:25]([CH3:32])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([N:33]4[CH:37]=[CH:36][C:35]([CH:38]([CH3:40])[CH3:39])=[N:34]4)[N:21]=3)[CH2:16][CH:15]2[C:41](=[O:50])[N:42]([CH2:44][CH2:45][CH2:46][CH2:47][CH:48]=[CH2:49])[CH3:43])=[O:13])[CH2:8][CH:7]1C=C)=[O:5])[CH3:2]>CC(C)OC1C(C=[Ru](Cl)([P](C2CCCCC2)(C2CCCCC2)C2CCCCC2)Cl)=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]12[CH2:7][CH:8]1[CH:49]=[CH:48][CH2:47][CH2:46][CH2:45][CH2:44][N:42]([CH3:43])[C:41](=[O:50])[CH:15]1[CH:14]([CH2:18][CH:17]([O:19][C:20]3[C:29]4[C:24](=[C:25]([CH3:32])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=4)[N:23]=[C:22]([N:33]4[CH:37]=[CH:36][C:35]([CH:38]([CH3:39])[CH3:40])=[N:34]4)[N:21]=3)[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of the diene (144) (230 mg, 0.335 mmol) and Hoveyda-Grubbs 1st generation catalyst (60.8 mg, 0.101 mmol) in dried and degassed 1,2-dichloroethane (230 mL) was heated at 80° C. under nitrogen for 18 h. Then, the solvent was evaporated and the residue purified by silica gel chromatography (ether) to give the target compound, m/z=659 (M+H)+.

Workup

customdegassed 1,2-dichloroethane (230 mL)
customThen, the solvent was evaporated
customthe residue purified by silica gel chromatography (ether)
customto give the target compound, m/z=659 (M+H)+

Sources & evidence

ORD record: ord-4bd0e6bd57cc4aa3a6fe2e7ecfbdd247
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659245B2

Reaction notes

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