Immunomodulators, compositions and methods there of
A technology of compounds and chelates, applied in the field of pharmaceutically active compounds
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Embodiment 1
[0203] The synthesis of embodiment 1 compound 1
[0204] (S)-1-((2-(2-Methyl-[1,1'-biphenyl]-3-yl)-6-(methylthio)benzo[d]oxazol-5-yl) Methyl)piperidine-2-carboxylic acid
[0205]
[0206] Step 1: Preparation of methyl 4-hydroxy-2-(methylthio)-5-nitrobenzoate
[0207]
[0208] Methyl 2-fluoro-4-hydroxybenzoate (20.00g) was dissolved in 200mL of acetic acid, cooled to 0-10°C in an ice bath, and concentrated nitric acid (10.1ml, 0.236mol) was dissolved in 40mL of acetic acid and slowly added dropwise to The above reaction solution; after the dropwise addition, remove the ice bath and naturally rise to room temperature and stir for 4-6h. The reaction solution was poured into ice water to quench the reaction. After stirring for 0.5h, the solid was completely precipitated, filtered, the filter cake was washed 2-3 times with water, dried, and the crude product was purified by flash chromatography (A. n-hexane; B.EA; B% from 0 to 30%, 20 minutes) to obtain 13.00 g Methyl 2-f...
Embodiment 2
[0228] The synthesis of embodiment 2 compound 2
[0229] ((2-(2-Methyl-[1,1'-biphenyl]-3-yl)-6-(methylthio)benzo[d]oxazol-5-yl)methyl)-L- proline
[0230]
[0231] Compound 2 was prepared essentially as described in Example 1 using the corresponding intermediate. For example, "L-proline" is used instead of "(S)-piperidine-2-carboxylic acid" in the last step above (step 7).
[0232] Basically according to the method described in Example 1, use instead of in step 1 of Example 29 To prepare the following examples (shown in Table 1), in some examples, the (S)-piperidine-2-carboxylic acid in step 7 above was replaced with other amic acids (such as L-proline).
[0233] Table 1
[0234]
[0235]
[0236]
[0237]
Embodiment 29
[0238] Synthesis of Example 29 Compound 29
[0239] (S)-1-((6-(difluoromethoxy)-2-(2-methyl-[1,1'-biphenyl]-3-yl)benzo[d]oxazole-5- base) methyl) piperidine-2-carboxylic acid
[0240]
[0241] Step 1: Preparation of methyl 2,4-dihydroxy-5-nitrobenzoate
[0242]
[0243] Methyl 2,4-dihydroxybenzoate (850 g, 5.06 mol) was dissolved in AcOH (3.6 L) and Ac 2 O (900mL) in the mixture. After cooling the clear solution to 10 °C (ice bath), add HNO within 1 h 3 (65%) (455ml) in AcOH (500mL). After the addition was complete, the temperature of the reaction mixture was raised to 15-20°C and stirring was continued for 1 hour. Until the raw materials are substantially completely reacted and the reaction is terminated. The reaction solution was poured into H 2 O (3 L), then the addition of the mixture was continued for 30 minutes without stirring. The precipitate was filtered and washed with a small amount of H 2 O rinse. The crude product was then poured into MeOH (2 L) wi...
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