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[ CAS No. 1106685-61-3 ] {[proInfo.proName]}

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Chemical Structure| 1106685-61-3
Chemical Structure| 1106685-61-3
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Product Details of [ 1106685-61-3 ]

CAS No. :1106685-61-3 MDL No. :MFCD16620532
Formula : C23H24N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 392.45 Pubchem ID :-
Synonyms :

Safety of [ 1106685-61-3 ]

Signal Word: Class:N/A
Precautionary Statements: UN#:N/A
Hazard Statements: Packing Group:N/A

Application In Synthesis of [ 1106685-61-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1106685-61-3 ]

[ 1106685-61-3 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 177036-94-1 ]
  • [ 74-88-4 ]
  • [ 1106685-61-3 ]
YieldReaction ConditionsOperation in experiment
96% Stage #1: ambrisentan With potassium carbonate In acetone for 0.5h; Stage #2: methyl iodide In acetone for 3h; 9 A mixture of (S)-ambrisentan (15.0 g, 40.0 mmol) and potassium carbonate (8.28 g, 60.0 mmol) in acetone (100 mL) is stirred for 0.5 hr. Methyl iodide (3 mL, 47.0 mmol) is slowly added drop-wise and then the reaction mixture is stirred for 3 hr. The resulting mixture is concentrated to dryness under reduced pressure. The residue is mixed with water (100 mL) and extracted with ethyl acetate (4 X 100 mL). The yield of the title compound is 15.0 g (96%). MS m/z 392.9 (M+ + 1).
  • 2
  • [ 35144-22-0 ]
  • [ 177036-78-1 ]
  • [ 1106685-61-3 ]
YieldReaction ConditionsOperation in experiment
72.96% With potassium carbonate; In N,N-dimethyl-formamide; at 90 - 92℃; for 1h;Inert atmosphere; Example 4:Preparation of (S)-methyl-2-(4,6-dimethylpyrimidin-2-yloxy)-3-methoxy-3,3- diphenylpropionate (compound ??; R' = methyl, R= methyl)To a stirred solution of (S)-methyl-2-hydroxy-3-methoxy-3,3-diphenylpropionate (compound IV; 79 gms/0.276 moles) and potassium carbonate(41.9gms / 0.303moles) in DMF (790 ml) was added 4,6-Dimethyl-2-(methyl sulfonyl) pyrimidine (compound III; R= methyl) (56.5 gms /0.303 moles) in a dry flask under nitrogen at 25-30C. The reaction mass was heated to 90-92C and further stirred for 1 hour. The reaction mass was charged with ethyl acetate (2.4 lit). The organic layer was washed with 2N citric acid (500 ml) followed by water and treated with charcoal. The clear filtrate was distilled completely under vacuum. The residue was stirred with n-heptane (300 ml), filtered and dried to obtain 90 gms of compound (II).The compound (II) was dissolved in acetonitrile (1.8 lit) and isolated in water (4.5 lit). The solid was isolated by filtration and dried to obtain 79 gms of compound (II).Efficiency: 72.96 % Purity by HPLC:99.8%Chiral purity: 99.97%
Example-12: Preparation of (+)-(2S)-2-[(4,6-dimethyIpyrimidin-2-yl)oxy]-3- methoxy-3,3-diphenylpropanoic acid methyl ester compound of formula-lOa:Mixture of (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester compound formula-8a (50 grams), dimethyl formamide (500 ml) and potassium carbonate (12 grams) was stirred at 40 minutes at 25-350C. 4,6-dimethyl-2- (methylsulphonyl) pyrimidine (34.5 grams) was added and heated to 90-950C and stirred for 4 hours. The reaction mixture was cooled to 25-35C. Water (250 ml) was added and stirred for 60 minutes. The solid obtained was filtered, washed with water and then dried at 60-700C to get the title compound. Yield: 55 grams M.R: 130-1400C; S.O.R: +135.8 (C= 0.5; MeOH)
Preparation of (+)-(2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoic acid methyl ester compound of formula-10a Mixture of (S)-2-hydroxy-3-methoxy-3,3-diphenylpropionic acid methyl ester compound formula-8a (50 grams), dimethyl formamide (500 ml) and potassium carbonate (12 grams) was stirred at 40 minutes at 25-35 C. 4,6-dimethyl-2-(methylsulphonyl)pyrimidine (34.5 grams) was added and heated to 90-95 C. and stirred for 4 hours. The reaction mixture was cooled to 25-35 C. Water (250 ml) was added and stirred for 60 minutes. The solid obtained was filtered, washed with water and then dried at 60-70 C. to get the title compound.Yield: 55 gramsM.R: 130-140 C.;S.O.R: +135.8 (C=0.5; MeOH)
  • 3
  • [ 1106685-61-3 ]
  • [ 177036-94-1 ]
YieldReaction ConditionsOperation in experiment
85.33% With water; sodium hydroxide In 1,4-dioxane at 40 - 45℃; for 33h; 5 Example 5:Preparation of (S)-2-(4,6-dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl propionic acid (compound I; R = methyl) Example 5:Preparation of (S)-2-(4,6-dimethylpyrimidin-2-yloxy)-3-methoxy-3,3-diphenyl propionic acid (compound I; R = methyl)To a stirred solution of (S)-methyl-2-(4,6-dimethylpyrimidin-2-yloxy)-3-methoxy-3,3- diphenylpropionate (compound II; R' = methyl, R= methyl) (79 gms /0.201 moles) in 1,4-dioxane (790 ml) was added 2 N NaOH solution (18.6 gms of NaOH in 450.0 ml of DI Water). The reaction mass was heated to 40-45°C and further stirred for 33 hours. The reaction mass was cooled to 25-30°C and quenched in water (7.9 Lit). The reaction mass was cooled to 10-15°C and acidified with cone. HCl. The solid was isolated by filtration and dried to yield 72.0 gms of the title compound (I).Compound (I) was further purified in N-methyl pyrrolidone/n-heptane, followed by DMSO/n-heptane to obtain 65.0 gms of the title compound (I).Efficiency: 85.33 %Chiral purity: 99.2%Purity by HPLC: 99.8%
Stage #1: (S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropionic acid methyl ester With water; sodium hydroxide In 1,4-dioxane at 25 - 90℃; Stage #2: With hydrogenchloride In water at 25 - 35℃; 13 Example-13: Preparation of ambrisentan compound of formula-la:Aqueous sodium hydroxide solution (10 grams in 250 ml of water) was added to the mixture of 1,4-dioxane (500 ml) and (+)-(2S)-2-[(4,6-dimethylpyrimidin-2-yi)oxy]-3- methoxy-3,3-diphenylpropanoic acid methyl ester (50 grams) compound of formula- 10a at 25-35°C, then heated to 85-90°C and stirred for 3 hours. The reaction mixture was cooled to 25-35°C and water (500 ml) was added. The reaction mixture was washed with ethylacetate. The pH of aqueous layer was adjusted to 1.8 with hydrochloric acid at 25-350C. The reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was distilled off under reduced pressure at below 60°C and then cooled to 0-5°C. The reaction mixture was stirred for 60 minutes at 0-50C. The obtained solid was filtered, washed with chilled ethyl acetate and dried at 60-700C to get the ambrisentan. Yield: 36 grams
Stage #1: (S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropionic acid methyl ester With water; sodium hydroxide In 1,4-dioxane at 25 - 90℃; for 3h; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 25 - 35℃; 13 Preparation of ambrisentan compound of formula-1a Aqueous sodium hydroxide solution (10 grams in 250 ml of water) was added to the mixture of 1,4-dioxane (500 ml) and (+)-(2S)-2-[(4,6-dimethylpyrimidin-2-yl)oxy]-3-methoxy-3,3-diphenylpropanoic acid methyl ester (50 grams) compound of formula-10a at 25-35° C., then heated to 85-90° C. and stirred for 3 hours. The reaction mixture was cooled to 25-35° C. and water (500 ml) was added. The reaction mixture was washed with ethylacetate. The pH of aqueous layer was adjusted to 1.8 with hydrochloric acid at 25-35° C. The reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was distilled off under reduced pressure at below 60° C. and then cooled to 0-5° C. The reaction mixture was stirred for 60 minutes at 0-5° C. The obtained solid was filtered, washed with chilled ethyl acetate and dried at 60-70° C. to get the ambrisentan. Yield: 36 grams
  • 4
  • [ 178306-52-0 ]
  • [ 1106685-61-3 ]
  • 5
  • [ 178306-47-3 ]
  • [ 1106685-61-3 ]
  • 6
  • [ 178306-51-9 ]
  • [ 1106685-61-3 ]
  • 7
  • [ 35144-22-0 ]
  • [ 1106685-61-3 ]
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