Biased agonists and their medicinal uses
A pharmacy, compound technology, applied in the field of biased agonists and their medicinal uses
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Embodiment 1
[0207] Example 1: 1-((S)-3-(benzo[d][1,3]dioxol-4-yl)-2-(dimethylamino)propyl)-3- Synthesis of ((S)-1-(thiophen-3-yl)propan-2-yl)urea (Ia-1)
[0208]
[0209] 1.1(S)-2-Amino-3-(benzo[d][1,3]dioxol-4-yl)propanamide (2a) and (S)-2-amino-3-( Synthesis of Benzo[d][1,3]dioxol-5-yl)propionamide (2b)
[0210]
[0211] Weigh 10.00g (40.70mmol) of L-benzo[d][1,3]dioxol-4-ylalanine (1a) or L-benzo[d][1,3]diol Oxol-5-ylalanine (1b) was placed in a 250 mL two-necked flask, and 150 mL of methanol was added, which could not be dissolved, and was a milky white suspension. Under ice bath and stirring, 14.50g (122.00mmol) thionyl chloride was slowly added dropwise, the exotherm was violent, the temperature was controlled below 10°C, the solution was gradually clarified, and after the addition of materials, the reaction was naturally raised to room temperature for 12h, and the reaction was complete after TLC detection. Stop the reaction. The reaction solution was transferred to a 250 ...
Embodiment 2
[0231] Example 2 1-((S)-3-(benzo[d][1,3]dioxol-4-yl)-2-(dimethylamino)propyl)-3-( Synthesis of 2-(thiophen-3-yl)ethyl)urea (Ia-2)
[0232]
[0233] 2.1 Synthesis of 4-nitrophenyl 2-(thiophen-3-yl)ethylcarbamate (6a-2)
[0234]
[0235] Weigh 3.55g (27.94mmol) of 3-ethylaminothiophene (5a-2) into a 500mL three-necked flask, add 50mL of ultra-dry THF in an ice bath, stir, and under argon protection, dropwise add 8.00mL (55.88mmol) of triethyl For the amine, 6.20 g (30.74 mmol) of phenyl p-nitrochloroformate was weighed, dissolved in 30 mL of ultra-dry THF, and added dropwise to the reaction solution. After the addition of materials, the temperature was naturally raised to room temperature, and the reaction was completed by TLC for 6 h, and the reaction was stopped. Add 100 mL of dichloromethane to dilute the reaction solution, filter with suction, and filter the filtrate through saturated NaHCO. 3 The solution (200 mL×3) and saturated brine (200 mL) were washed. The or...
Embodiment 3
[0239] Example 3 1-((S)-3-(benzo[d][1,3]dioxol-5-yl)-2-(dimethylamino)propyl)-3-( Synthesis of (S)-1-(thiophen-3-yl)propan-2-yl)urea (Ia-3)
[0240]
[0241] Weigh 0.46g (1.56mmol) of 4b and place it in a 50mL three-necked flask, add 15mL of acetonitrile under argon protection, add 0.70mL (4.69mmol) of triethylamine dropwise, heat up to 60°C, weigh 0.48g (1.56mmol) of 6a -1 was dissolved in 10 mL of acetonitrile and added dropwise to the reaction solution. The reaction solution turned from colorless to yellow. After the addition of materials, the temperature was raised to 80 °C and stirred for 8 h. The reaction was complete after TLC detection. The reaction was stopped, suction filtered, the filtrate was evaporated to dryness under reduced pressure, and the residue was dissolved in 30 mL of EA / isopropanol (2:1) mixed solvent. The solution was pH= 9 NaCO 3 / NaHCO 3 Buffer wash 20mL×3. The organic phase was dried over anhydrous sodium sulfate, concentrated under reduced p...
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