Nitrogen → 17-[2-(3-Fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acid ethyl ester

HRID 1443505Notes

Reaction equation

HRID 1443505 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]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=4)[N:21]=3)[CH2:16][CH:15]2[C:40](=[O:49])[N:41]([CH2:43][CH2:44][CH2:45][CH2:46][CH:47]=C)[CH3:42])=[O:13])[CH2:8][CH:7]1[CH:9]=C)=[O:5])[CH3:2].N#N>ClCCCl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3OC(C)C)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1>[CH2:1]([O:3][C:4]([C:6]12[CH2:8][CH:7]1[CH:9]=[CH:47][CH2:46][CH2:45][CH2:44][CH2:43][N:41]([CH3:42])[C:40](=[O:49])[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]([C:33]4[CH:38]=[CH:37][CH:36]=[C:35]([F:39])[CH:34]=4)[N:21]=3)[CH2:16]1)[C:12](=[O:13])[NH:11]2)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 947NitrogenHCID 684124351-{[4-[2-(3-Fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-2-(hex-5-enyl-methyl-carbamoyl)-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 6841130717-[2-(3-Fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diaza-tricyclo[13.3.0.0*4,6*]octadec-7-ene-4-carboxylic acid ethyl esterYield 70%

Reagents, catalysts & solvents 2

HCID 11763533(1,3-Bis(2,4,6-trimethylphenyl)imidazolidin-2-ylidene)(dichloro)((2-((propan-2-yl)oxy)phenyl)methylidene)rutheniumCatalystHCID 111,2-DichloroethaneSolvent

Procedure

The diene 157 (0.70 g, 1.041 mmol) was dissolved in dry DCE (0.7 L). The solution was put under inert atmosphere (N2) and catalyst (Hoveyda Grubbs 2nd generation, 70 mg, 0.113 mmol) was added to the solution. The reaction mixture was refluxed for 16 h, cooled to room temperature and evaporated on silica by rotary evaporation. The product was purified by flash chromatography (heptane:ethyl acetate 1:1) which gave the title compound (0.466 g, 70%), LRMS (M+H) 645.

Workup

  1. additionwas added to the solution
  2. temperatureThe reaction mixture was refluxed for 16 h
  3. customevaporated on silica by rotary evaporation
  4. customThe product was purified by flash chromatography (heptane:ethyl acetate 1:1) which

Sources & evidence

ORD record
ord-0062891b9fc14939a38b833a9d7d072d
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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