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[ CAS No. 112885-42-4 ] {[proInfo.proName]}

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Chemical Structure| 112885-42-4
Chemical Structure| 112885-42-4
Structure of 112885-42-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 112885-42-4 ]

CAS No. :112885-42-4 MDL No. :MFCD01666680
Formula : C27H33ClFN3O10 Boiling Point : -
Linear Structure Formula :- InChI Key :HUZTYZBFZKRPFG-UHFFFAOYSA-N
M.W : 614.02 Pubchem ID :119583
Synonyms :
AS-4370 citrate;TAK-370 citrate;Mosapride (citrate);Gasmotin;AS-4370;TAK-370

Calculated chemistry of [ 112885-42-4 ]

Physicochemical Properties

Num. heavy atoms : 42
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.41
Num. rotatable bonds : 13
Num. H-bond acceptors : 12.0
Num. H-bond donors : 6.0
Molar Refractivity : 151.88
TPSA : 208.95 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -11.1 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.1
Log Po/w (XLOGP3) : -1.48
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 0.34
Log Po/w (SILICOS-IT) : 3.68
Consensus Log Po/w : 1.48

Druglikeness

Lipinski : 3.0
Ghose : None
Veber : 2.0
Egan : 1.0
Muegge : 4.0
Bioavailability Score : 0.11

Water Solubility

Log S (ESOL) : -2.07
Solubility : 5.25 mg/ml ; 0.00855 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 2.43 mg/ml ; 0.00395 mol/l
Class : Soluble
Log S (SILICOS-IT) : -6.65
Solubility : 0.000137 mg/ml ; 0.000000223 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.42

Safety of [ 112885-42-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 112885-42-4 ]

* 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 [ 112885-42-4 ]
  • Downstream synthetic route of [ 112885-42-4 ]

[ 112885-42-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 112885-41-3 ]
  • [ 112885-42-4 ]
YieldReaction ConditionsOperation in experiment
86% With citric acid In water at 0℃; Heating / reflux To the suspension of 1.3 g (2.5 [MMOL)] of compound [(VIII)] and 3 ml of water 12 m of [1 37percent] aqueous hydrochloric acid solution is added. The obtained solution is stirred at 40 [C] for 3 hours, cooled to 10 [C] and 38 mi of 4 M aqueous sodium hydroxide solution added dropwise. The precipitated mosapride base of formula IX is filtered, washed 2 x with water, to give 1.05 g (100percent) of the compound of formula [(IX).] 1.01 g of mosapride base of formula [(IX)] obtained the above manner is warmed to boiling with 25 [ML] of 10percent aqueous citric acid solution with stirring, cooled to 0 [C,] the precipitated product filtered, washed 2 x with water to give 1.34 g (86 percent) of the title compound. Mp: [110-113C.]
Reference: [1] Patent: WO2003/106440, 2003, A2, . Location in patent: Page 10
  • 2
  • [ 77-92-9 ]
  • [ 112885-42-4 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With sodium hydroxide In dichloromethane; water for 0.5 h; Heating / reflux
Stage #2: at 0℃; for 0.5 h; Heating / reflux
1.04 g (2 [MMOL)] of compound [(VIII)] and 15 mi of 1.77 M hydrochloric acid in ethyl acetate are stirred at 50 [C] for 2 hours and at 0 [C] for 2 hours. The precipitated crystals are filtered and washed 2 x with cooled ethyl acetate to give 0.93 g (94 percent) mosapride dihydrochloride. Mp. 144-155 [C.] To the mosapride [DIHYDROCHLORIDE] salt obtained the above manner, 20 ml of [DICHLOROMETHANE,] 10 [ML] of water and 1.2 [ML] of 4 M aqueous sodium hydroxide solution are added. The organic phase is separated and the aqueous phase extracted with [2X10] [ML] of [DICHLOROMETHANE.] The combined organic phases are dried over anhydrous sodium sulphate, filtered and the solvent evaporated under reduced pressure. To the residue 23 [ML] of 10percent aqueous citric acid solution is added, refluxed for 30 minutes and cooled to 0 [C.] The precipitated product is filtered and washed 2 x with water to give 0.91 g (88percent) of the title compound. Mp : [110-113 C.]
Reference: [1] Patent: WO2003/106440, 2003, A2, . Location in patent: Page 9-10
  • 3
  • [ 636582-76-8 ]
  • [ 112885-42-4 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With sodium hydroxide In dichloromethane; water
Stage #2: With citric acid In water
The solution of 1.04 g (2 [MMOL)] of compound [(VIII),] 13 ml of [DICHLOROMETHANE] and 0.77 mi of trifluoroacetic acid is stirred at room temperature for 6 hours. The reaction mixture is evaporated under reduced pressure, crystallized from ether, filtered and washed with ether to give 1.01 g (94 percent) trifluoroacetate salt of the title compound. Mp: [186-193C.] 0.99 g (1.85 [MMOL)] of mosapride trifluoroacetate salt obtained the above manner is treated substantially the same manner as in Example A) to give 0,99 g (83percent) of citrate dihydrate salt of the title compound. Mp: [110-113C.]
Reference: [1] Patent: WO2003/106440, 2003, A2, . Location in patent: Page 10
  • 4
  • [ 112885-34-4 ]
  • [ 77-92-9 ]
  • [ 112885-42-4 ]
YieldReaction ConditionsOperation in experiment
88.7% at 50 - 65℃; 4-Acetylamino-5-chloro-2-ethoxy-n-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide (20.00 g, 0.046 mol)Into a reaction flask containing 200 ml of methanol,The solution was heated and refluxed at 65 ° C, dissolved completely, cooled to 50 ° C, and an aqueous solution of citric acid was added.The reaction is kept for 30-45 minutes. After the reaction, the temperature is lowered, crystallization, suction filtration,Mosapride citrate was obtained (yield 88.7percent, purity 99.93percent).
Reference: [1] Patent: CN108341788, 2018, A, . Location in patent: Paragraph 0069; 0070; 0074; 0079; 0080; 0081-0087
  • 5
  • [ 112885-41-3 ]
  • [ 77-92-9 ]
  • [ 112885-42-4 ]
YieldReaction ConditionsOperation in experiment
95.45% at 80 - 110℃; for 0.5 h; Citric acid monohydrate (84.67 g) and water (850 ml) were charged at ambient temperature and stirred to dissolve the solid. The reaction mass was heated up to 80°C and mosapride free base (85 g) was charged at 80°C. The heterogeneous mass was stirred and heated up to reflux (95 °C to 110°C). The clear solution was stirred at reflux temperature for 30 minutes. The reaction mass was cooled down to 0°C and was stirred at 0°C to 5°C for 30 minutes. The solid was filtered and washed with water (2 X 170 ml). The solid was suck dried and unloaded. The solid was dried at 60°C for 15 hours under vacuum to give the title compound.Yield: 125 g (95.45percent)Water content: 6.28percentD-II Impurity: 0.269
94.7% at 50℃; for 1 h; General procedure: Stirring blade, three-necked flask 100mL fitted with a thermometer, HPLC and thepurity 99.94percent of the amide compound 10.0g (23.8mmol) prepared in Preparation Example 1,ethanol 80g, and water 80g was added, stirring to obtain a slurry. The resulting slurry waswarmed to 50 ° C. Then, 13.6g citric acid (71.2mmol) was dropped to gradually the slurry overa period of (temperature 50 ° C of the aqueous solution) for 10 minutes aqueous solution ofcitric acid dissolved in water 20g, amide compound and citric acid was reacted (the temperatureof the reaction solution at the time of aqueous citric acid dropwise addition was adjusted to 50 °C (reaction temperature 50 ° C)). After the aqueous solution of citric acid dropping, and allowedto react for 1 hour at 50 ° C (reaction temperature 50 ° C. The reaction solution wasconfirmed by visual observation that became clear during this time. ). Thereafter, the resultantreaction solution was cooled slowly to 10 ° C, and held for 1 hour. The precipitated solid wasfiltered off by vacuum filtration and the cake was washed twice with water 30g. Obtained afterdrying under reduced pressure a white solid at an external temperature of 40 ° C, as a whitesolid 4-amino-5-chloro-2-ethoxy -N - [[4- (4-fluoro-benzyl) -2-morpholinyl] methyl] It wasobtained benzamide citrate 2 hydrate (citrate dihydrate) 14.1g (21.8mmol). Yield: 91.4percent, HPLCpurity: 99.94percent, by-products: (not detected) undetected, water content: 5.8percent, quantitative value:was 100.5percent. The results are shown in Table 1. Incidentally, the yield of citrate dihydrate is avalue obtained by measuring the mass of simply obtained solid.
Reference: [1] Patent: WO2011/107903, 2011, A1, . Location in patent: Page/Page column 11
[2] Patent: JP5743474, 2015, B2, . Location in patent: Paragraph 0065; 0069; 0071
  • 6
  • [ 133-10-8 ]
  • [ 112885-42-4 ]
Reference: [1] Patent: CN108341788, 2018, A,
[2] Patent: CN108341788, 2018, A,
[3] Patent: CN108341788, 2018, A,
[4] Patent: CN108341788, 2018, A,
[5] Patent: CN108341788, 2018, A,
  • 7
  • [ 50-86-2 ]
  • [ 112885-42-4 ]
Reference: [1] Patent: CN108341788, 2018, A,
[2] Patent: CN108341788, 2018, A,
[3] Patent: CN108341788, 2018, A,
[4] Patent: CN108341788, 2018, A,
[5] Patent: CN108341788, 2018, A,
  • 8
  • [ 459-57-4 ]
  • [ 112885-42-4 ]
Reference: [1] Patent: CN108341788, 2018, A,
[2] Patent: CN108341788, 2018, A,
[3] Patent: CN108341788, 2018, A,
[4] Patent: CN108341788, 2018, A,
[5] Patent: CN108341788, 2018, A,
  • 9
  • [ 2486-67-1 ]
  • [ 112885-42-4 ]
Reference: [1] Patent: CN108341788, 2018, A,
[2] Patent: CN108341788, 2018, A,
[3] Patent: CN108341788, 2018, A,
[4] Patent: CN108341788, 2018, A,
[5] Patent: CN108341788, 2018, A,
  • 10
  • [ 22116-33-2 ]
  • [ 112885-42-4 ]
Reference: [1] Patent: CN108341788, 2018, A,
[2] Patent: CN108341788, 2018, A,
[3] Patent: CN108341788, 2018, A,
[4] Patent: CN108341788, 2018, A,
[5] Patent: CN108341788, 2018, A,
  • 11
  • [ 112914-13-3 ]
  • [ 112885-42-4 ]
Reference: [1] Patent: CN108341788, 2018, A,
  • 12
  • [ 112885-42-4 ]
  • [ 112885-41-3 ]
Reference: [1] Patent: US2012/64162, 2012, A1,
[2] Patent: EP2433652, 2012, A1,
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[ 112885-42-4 ]

Chemical Structure| 112885-41-3

A194108[ 112885-41-3 ]

4-Amino-5-chloro-2-ethoxy-N-((4-(4-fluorobenzyl)morpholin-2-yl)methyl)benzamide

Reason: Free-salt