1-((4-methylphenyl)methyl)-1H-pyrazole-4-carboxylic acid → 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

Reactant 3

HCID 196200321-((4-methylphenyl)methyl)-1H-pyrazole-4-carboxylic acid

HCID 43565332HCID 43565332, compound

HCID 131732190HCID 131732190, compound2×

Product 1

HCID 178425449HCID 178425449, compound

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%.