1006452-67-0 → HCID 178425449, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([CH3:25])([CH3:24])[O:18][SiH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:26]1[C:27](=[O:41])[N:28]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:29]=[C:30]([NH2:32])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:42][C:43]1[CH:57]=[CH:56][C:46]([CH2:47][N:48]2[CH:52]=[C:51]([C:53](O)=[O:54])[CH:50]=[N:49]2)=[CH:45][CH:44]=1.FC1C=CC(CN2C=C(C(O)=O)C=N2)=CC=1>>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([CH3:25])([CH3:24])[O:18][SiH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:26]1[C:27](=[O:41])[N:28]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[CH:29]=[C:30]([NH:32][C:53]([C:51]2[CH:50]=[N:49][N:48]([CH2:47][C:46]3[CH:56]=[CH:57][C:43]([CH3:42])=[CH:44][CH:45]=3)[CH:52]=2)=[O:54])[CH:31]=1)=[O:7])([CH3:2])([CH3:4])[CH3:3]Participants
4
Procedure
The title compound was prepared by the route outlined in Scheme 8 and using the experimental from Example 20, step 4, with intermediate (8d), 2-[5-amino-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]-5-(tert-butyl-dimethyl-silanyloxymethyl)-indole-1-carboxylic acid tert-butyl ester (1.0 g, 1.67 mmol) and 1-(4-methyl-benzyl)-1H-pyrazole-4-carboxylic acid (0.43 g, 1.99 mmol) which had been synthesised according to the protocol described for intermediate (6e) in example 21. The resultant crude product was purified by flash chromatography on SiO2 with hexane—50% ethyl acetate/hexane (gradient) to afford the title compound as a pink oil, 0.721 g, 54%.
Workup
- customThe title compound was prepared by the route
- customThe resultant crude product was purified by flash chromatography on SiO2 with hexane—50% ethyl acetate/hexane (gradient)
Sources & evidence
- ORD record
- ord-1e6e11bf646e40eca0e34901294f6190
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916591B2
Reaction notes
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