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Chemical Structure| 100643-71-8
Chemical Structure| 100643-71-8
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Product Details of [ 100643-71-8 ]

CAS No. :100643-71-8 MDL No. :MFCD00871949
Formula : C19H19ClN2 Boiling Point : -
Linear Structure Formula :- InChI Key :JAUOIFJMECXRGI-UHFFFAOYSA-N
M.W : 310.82 Pubchem ID :124087
Synonyms :
Sch34117;Descarboethoxyloratadine;Aerius;Neoclarityn;Clarinex;NSC 675447

Calculated chemistry of [ 100643-71-8 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.32
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 95.47
TPSA : 24.92 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.04
Log Po/w (XLOGP3) : 4.5
Log Po/w (WLOGP) : 3.64
Log Po/w (MLOGP) : 3.66
Log Po/w (SILICOS-IT) : 5.17
Consensus Log Po/w : 4.0

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.01
Solubility : 0.00307 mg/ml ; 0.00000987 mol/l
Class : Moderately soluble
Log S (Ali) : -4.74
Solubility : 0.0056 mg/ml ; 0.000018 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.38
Solubility : 0.0000129 mg/ml ; 0.0000000416 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.21

Safety of [ 100643-71-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 100643-71-8 ]

* 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.

  • Upstream synthesis route of [ 100643-71-8 ]
  • Downstream synthetic route of [ 100643-71-8 ]

[ 100643-71-8 ] Synthesis Path-Upstream   1~13

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Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 22, p. 9473 - 9479
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  • [ 79794-75-5 ]
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YieldReaction ConditionsOperation in experiment
98.5% Reflux; Inert atmosphere; Alkaline conditions 40g of loratadine, 40g of sodium hydroxide, 500ml of absolute ethanol and 125ml of purified water were added to the reaction flask, The reaction solution was concentrated to a large amount of solid precipitated, filtered, washed and dried to obtain desloratadine 32 g, the yield was 98.5percent. The reaction was carried out under nitrogen atmosphere. (Molar ratio of loratadine to alkali is 1: 20; the ratio of purified water to anhydrous ethanol is 1: 4)
98.5% With C22H40N4(2+)*2BF4(1-) In toluene at 80℃; for 0.666667 h; 0.1 mol of loratadine was dissolved in 20 g of [DBU- (CH2) 4-DBU2 +] 2BF4-,Water bath heated to 80 degrees Celsius,Stirring reaction 30min (no reflux and other devices);Then add 20 mL of toluene to continue stirring for 10 min,Static cooling stratification,Collect the organic layer, recover the ionic liquid, ammonia water after washing,The solvent is removed under reduced pressure to give desloratadine,The yield was 98.5percent and the HPLC purity was 99.98percent.
96% at 80℃; for 0.5 h; Green chemistry 0.1 mol loratadine raw material was dissolved in 20g of [DBU-(CH2)4-DBU2 +] 2Br-. The water bath is heated to 80 degrees Celsius. Stir the reaction for 30min (without reflux and other devices); then add 20 ml toluene to continue stirring 10min, layered cooling at a standstill, the collection of the organic layer, after ammonia washing, the solvent is removed under reduced pressure, to obtain desloratadine, calculating yield 96percent, HPLC purity test 99.98percent.
96% at 80℃; for 0.5 h; A solution of 0.1 mol of loratadine was dissolved20 g of [DBU- (CH2) 4-DBU2 +] · SO42-,Water bath heated to 80 degrees Celsius,Stirring reaction 30min (no reflux and other devices);Then add 20 mL of toluene to continue stirring for 10 min,Static cooling stratification,Collecting organic layer,Recovery of ionic liquid, ammonia washing, the solvent removed under reduced pressure, you can get desloratadine,The calculated yield was 96percentThe HPLC purity was 99.98percent.
93.3% With water; sodium hydroxide In ethanolReflux To a solution of ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylate (383 mg, 1 mmol) in ethanol, a 30percent sodium hydroxide aqueous solution was added.
The mixture was refluxed overnight.
The solvent was distilled off, and the resulting residue was dissolved in water and neutralized with concentrated hydrochloric acid.
The extraction with ethyl acetate was performed 3 times, and the combined organic layer was dried over magnesium sulfate.
The solvent was distilled off, and thus the title compound (290 mg, 93.3percent) was obtainedasayellowish white solid.
1H-NMR (CDCl3, δ): 2.3-2.4 (4H,m), 2.6-2.9 (4H,m) 3.0-3.1 (2H,m), 3.2-3.5 (2H,m), 7.1-7.2 (4H,m), 7.43 (1H,dd,J=1.4 Hz, 7.6 Hz), 8.40 (1H,dd,J=1.6 Hz, 4.9 Hz)
91.5% With sodium hydroxide In 2-methoxy-ethanol; water for 2 - 3 h; Heating / reflux 100 ml of 2-methoxyethanol (methylcellosolve), 10 ml of an aqueous 40percent sodium hydroxide solution, 2.5 g of sodium hydroxide and 12.5 g (32.65 moles) of loratadine are weighed in a vessel equipped with an intensive stirrer. The mixture is boiled for three hours. The end of the reaction is monitored with TLC. Preparation:90 ml 2-methoxyethanol are distilled off from the reaction mixture, whereupon 100 ml of icecold water and 100 ml of ethyl acetate are added to the residue. After the separation the organic layer is dried, the solvent is evaporated and the residue is crystallised from a mixture of hexane : ethyl acetate in a ratio of 10:1.Yield: 9.28 g (91.5percent) almost white crystalsMp.: 149-151 °C.Elementary analysis:C19Hi9ClN2 (310.8)Calculated: C:73.42 H:6.16 Cl:11.41 N:9.01Found: C:73.38 H:6.22 01:11.44 N:9.04HPLC purity: 99.1percent.; Example 3; Preparation of pseudopolymorph of desloratadine with half moles of carbon dioxide; 100 ml of 2-methoxyethanol (methylcellosolve), 12 ml of an aqueous 50percent sodium hydroxide solution and 12.5 g of loratadine are weighed in a vessel equipped with vigorous stirrer. The mixture is boiled for two hours. The end of the reaction is monitored with TLC. Preparation:90 ml 2-methoxyethanol are distilled off from the reactionmixture, whereupon 100 ml of icecold water and 100 ml ofethyl acetate are added to the residue. After the separation, ofthe layers the organic layer is clarified, dried, and 5.0 g dry iceare added to the pale yellow solution in small parts during halfhours. The crystals precipitate and the cold solution is filtered,the crystals obtained washed with ethyl acetate.Yield: 9.61 g (88.4 percent) almost white crystals.Analysis: C19H19C1N2X 1/2C02 (332.87)Mp.: 144-148 °C (slowly dec. above 100 °C)Calculated: C:70.71 H:5.79 Cl:10.62 N:8.41Found: C:70.01 H:5.86 Cl:10.51 N:8.38HPLC purity: 99.7 percent .; Example 5; Preparation of desloratadine hydrobromide (1:1); A mixture of 100 ml of 2-methoxyethanol (methylcellosolve) 10 ml of an aqueous 40percent sodium hydroxide solution, 2.5 g of sodium hydroxide and 12.5 g (32.65 moles) of loratadine are weighed in a vessel equipped with vigorous stirrer. The mixture is boiled for three hours. The end of the reaction is monitored with TLC.Preparation:90 ml 2-methoxyethanol is distilled off from the reactionmixture under reduced pressure, whereupon 100 ml of theicecold water and 100 ml of ethyl acetate are added to theresidue. After the separation of layers the product is extractedfrom the organic layer with a mixture of 5 ml of concentratedhydrochloric acid and 100 ml of icecold water. The aqueouslayer is clarified with activated carbon then filtered.Desloratadine base is set free with 5 ml of a 40percent sodiumhydroxide solution, extracted with 120 ml of ethyl acetate anddried. The base content of the pale yellow solution isdetermined, whereupon a solution of an equimolecular amountof hydrogen bromide in ethyl acetate is added. The whitecrystalline product is filtered at 0 °C, washed with ethanol.Yield: 7.33 g (93.6 percent) white crystals.Mp.: 268-272 °C (transformed at 198-200 °C )Analysis for the formula C19H19C1N2 * HBr (391.74)Calculated: C:58.26 H:5.15 Br:20.40 Cl:9.05 N:7.15Found: 58.08 H:5.17 Br:20.45 Cl:9.05 N:7.14HPLC purity >99.7percent
87.5% With sodium hydroxide In methanol at 82 - 95℃; for 2 - 12 h; Heating / reflux mixture of 8-chloro-6, 11-dihydro-11- (1-ethoxycarbonyl-4-piperidilydene)-5H-benzo [5, 6] cyclohepta [1,2-b] pyridine (100 [GM,] 0.2612 mole), sodium hydroxide (110 gm, 2.75 mole) in methanol (400 [ML,] 9.89 mole) was refluxed for 2 hrs at 82o to [95OC.] After completion of reaction, 1000 ml of water is added to obtain crystals of 8-chloro-6,11- [DIHYDRO-LL- (4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta [1,2-b] pyridine, which was filtered at 25o-30oC, washed with plenty of water to remove salts, dried at [50-55OC.] The isolated yield was 76 gm. , with a purity of 99.8percent (OAB, HPLC) and an absorbance of 0.043 at 430 [NM.] giving a yield of 93.6percent The structure of the compound was confirmed by comparison of its [I. R., NMR] and Mass Spectra of reference standards. The quality results are shown in Table-3. The reaction is carried out as described in Example 1, but the amount of methanol used was [600ML] (14.83 mole) instead of [400ML.] The reaction was completed in 12 hrs. The isolated yield of [8-CHLORO-6,] [11-DIHYDRO-11-(4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta (1,2-b) pyridine was 72 gm with a purity of 99.6percent (OAB, HPLC) and an absorbance of [0. 083] at 430 nm. giving a yield of 88.7percent The reaction was carried out as described in Example 1, but the amount of sodium hydroxide used was 92 gm (2.3 mole) instead of [110 GM.] The reaction is completed in 8 hrs. The isolated yield [OF 8-CHLORO-6, 11-DIHYDRO-LL- (4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta (1,2-b) pyridine was 71 gm with a purity of 99.7percent (OAB, HPLC) and an absorbance of 0.09 at 430 nm. giving a yield of 87.5percent
82.5% With potassium hydroxide In butan-1-ol for 1 h; The reaction was carried out as described in Example 1, but the n-butanol [(400ML,] 4.37 mole) and potassium hydroxide (160gm, 2.857 mole) were used instead of methanol [(400ML)] and sodium hydroxide [(11 OGM).] The reaction is completed in one hrs. The isolated yield [OF 8-CHLORO-6, 11-DIHYDRO-11-(4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta (1,2-b) pyridine was 74 gm which is further purified in methanol-isopropyl to get product with a purity of 99.7percent (OAB, HPLC) and an absorbance of 0.08 (430 [NM)] giving a yield of 82. 5percent.
82.5% With potassium hydroxide In isopropyl alcohol for 1 - 50 h; The reaction was carried out as described in Example [1,] but the isopropanol [(400ML,] 5.23 mole) and potassium hydroxide (160gm, 2.857 mole) were used instead of methanol [(400ML)] and sodium hydroxide [(LLOGM).] The reaction is completed in 4 hrs. The isolated yield of 8-chloro-6, [11-DIHYDRO-11-(4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta (1,2-b) pyridine was 75 gm with a purity of 99.6percent (OAB, HPLC) and an absorbance of 0.27 at 430 [NM.] giving a yield of 92.4percent further purification as in example 4 results in the compound with absorbance of 0.07. The yield has increased to 83.8percent The reaction was carried out as described in Example 5, but the amount of isopropanol and potassium hydroxide used was one litre (21.23 mole) and [100GM] (1.786 mole) respectively instead of [400ML] and 160 gm. The reaction is completed in 50 hrs. The isolated yield of 8- chloro-6, [11-DIHYDRO-11-(4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta (1,2-b) pyridine was 76 gm with a purity of 99.7percent (OAB, HPLC) and an absorbance of 0.2 at 430 nm. giving a yield of 93.62percent On purification yield was 82.5 and colour absorbance was 0.06.
81.3% With potassium hydroxide In benzyl alcohol for 1.5 h; The reaction was carried out as described in Example 1, but the benzyl alcohol [(400ML,] 3.87 mole) and potassium hydroxide (160gm, 2.857 mole) were used instead of methanol [(400ML)] and sodium hydroxide [(110GM).] The reaction is completed in 1.5 hrs. The isolated yield of 8-chloro-6, [11-DIHYDRO-11-(4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta (1,2-b) pyridine was 74 gm as base. This was crystallized in methanol-isopropyl ether to get a purity of 99.6percent (OAB, HPLC) and an absorbance of 0.09 (430 [NM)] giving a yield of 66gm (81.3percent).
81.3% With potassium hydroxide In propan-1-ol for 1 h; The reaction was carried out as described in Example [1,] but the n-propanol [(400ML,] 5.36 mole) and potassium hydroxide (160gm, 2.857 mole) were used instead of methanol (400ml) and sodium hydroxide (110gm). The reaction is completed in one hrs. The isolated yield of 8-chloro-6, 11-dihydro- 11 -(4-piperidilydene) - 5H-benzo [5,6] cyclohepta (1,2-b) pyridine was 74 gm with a purity of 99.47percent giving a yield of 91.2percent. Further purification in methanol-isopropyl ether was achieved to get a yield of 66gm (81.3percent) with an absorbance of 0.08 (430 [NM).]
80.1% With sodium hydroxide In butan-1-ol for 3 h; The reaction was carried out as described in Example 1, but the n-butanol [(400ML,] 4.37 mole) was used instead of methanol [(400ML)] The reaction is completed in 3 hrs. The isolated yield [OF 8-CHLORO-6, 11-DIHYDRO-11-(4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta (1,2-b) pyridine was 72 gm with a purity of 99.6percent (OAB, HPLC) giving a yield of 88.7percent. This was further purified to get an absorbance of 0.08 and yield of 65 gm (80. [1percent).]
80.1% With sodium hydroxide In benzyl alcohol for 3 h; The reaction was carried out as described in Example 1, but the benzyl alcohol [(400ML,] 3.87 mole) was used instead of methanol (400ml). The reaction is completed in 3 hrs. The isolated yield [OF 8-CHLORO-6, 11-DIHYDRO-11-(4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta (1,2-b) pyridine was 73 gm which was further purified in methanol-isopropyl ether to get purity 99.76percent (OAB, HPLC) and an absorbance of 0.08 (430 nm) giving a yield of 80. [1percent.]
78.8% With sodium hydroxide In propan-1-ol for 4 h; The reaction was carried out as described in Example 1, but the n-propanol [(400ML,] 5.36 mole) was used instead of methanol [(400ML).] The reaction is completed in 4 hrs. The isolated yield of 8-chloro-6, [11-DIHYDRO-11-(4-PIPERIDILYDENE)-5H-BENZO] [5,6] cyclohepta (1,2-b) pyridine was 72 gm with a purity of 99.5percent (OAB, HPLC) giving a yield of 88. [7percent.] Further purification in methanol-isopropyl ether provides the yield of 64 gm (78.8 percent) with an absorbance of 0.09 (430 nm).
77.6% With sodium hydroxide In ethanol for 5 h; The reaction was carried out as described in Example 1, but the ethanol (400 [ML,] 6.83 mole) was used instead of methanol (400ml). The reaction is completed in 5 hrs. The isolated yield [OF 8-CHLORO-6, 11-DIHYDRO-11-(4-PIPERIDILYDENE)-5H-BENZO] [5, [6]] cyclohepta (1,2-b) pyridine was 72 gm with a purity of 99.5percent (OAB, HPLC) and an absorbance of 0.6 at 430 nm. giving a yield of 88.7percent Further purification with methanol-isopropyl ether results in 92percent yield, and 0.1 absorbance.
48% With sodium hydroxide; polyethylene glycol 400 In toluene for 2 h; Heating / reflux EXAMPLE 1 Step-i-Preparation of 8-chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (Desloratadine) To a solution of loratadine (50 gms) in toluene (200 ml), polyethylene glycol 400 (100 ml) was added and stirred. Sodium hydroxide (50 gms) was added to the above reaction mixture and refluxed for 2 hours. The course of the reaction was monitored by HPLC and after completion of the reaction, water (750 ml) and toluene (100 ml) was added and stirred well. The organic layer was separated out; the aqueous layer was extracted with toluene (2.x.100 ml). The combined organic layer was washed with water (2.x.250 ml) followed by brine (1.x.250 ml) and evaporated the solvent under vacuum. Recrystallization The obtained solid was dissolved in the mixture of toluene: methylisobutyl ketone (1:1 v/v) at 85° C., followed by the addition of IPE at 60° C. and cooled to 5° C. to 10° C. The obtained solid was filtered off. This recrystallization may be repeated to obtain the desired quality and purity of Desloratadine. Yield: 19.0 gms (48.0percent).
48% With sodium hydroxide In decaethylene glycol; toluene for 2 h; Heating / reflux Example 1; Step-i-Preparation of 8-chloro-6,l 1-dihydro-l l-(4-piperidinyIidene)-5H- benzof5,61cycloheptafl,2-b1pyridine (Desloratadine); To a solution of loratadine (50 gms) in toluene (200 ml), polyethylene glycol 400 (100 ml) was added and stirred. Sodium hydroxide (50 gms) was added to the above reaction mixture and refluxed for 2 hours. The course of the reaction was <n="6"/>monitored by HPLC and after completion of the reaction, water (750 ml) and toluene (100 ml) was added and stirred well. The organic layer was separated out; the aqueous layer was extracted with toluene (2 X 100 ml). The combined organic layer was washed with water (2 X 250 ml) followed by brine (1 X 250 ml) and evaporated the solvent under vacuum.Recrvstallization :The obtained solid was dissolved in the mixture of toluene : methylisobutyl ketone (1:1 v/v) at 85°C, followed by the addition of IPE at 60°C and cooled to 5° C to 10° C. The obtained solid was filtered off. This recrystallization may be repeated to obtain the derived quality of Desloratadine.Yield: 19.0 gms (- 48.0 percent).

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Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 1, p. 457 - 461
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Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 22, p. 9473 - 9479
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