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[ CAS No. 123853-39-4 ] {[proInfo.proName]}

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Chemical Structure| 123853-39-4
Chemical Structure| 123853-39-4
Structure of 123853-39-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 123853-39-4 ]

CAS No. :123853-39-4 MDL No. :MFCD06654363
Formula : C16H15Cl2NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :LHAOQTPGTBGTIG-UHFFFAOYSA-N
M.W : 356.20 Pubchem ID :2794058
Synonyms :

Calculated chemistry of [ 123853-39-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 91.4
TPSA : 75.63 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 3.17
Log Po/w (WLOGP) : 3.11
Log Po/w (MLOGP) : 2.53
Log Po/w (SILICOS-IT) : 3.41
Consensus Log Po/w : 2.94

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.97
Solubility : 0.0378 mg/ml ; 0.000106 mol/l
Class : Soluble
Log S (Ali) : -4.43
Solubility : 0.0133 mg/ml ; 0.0000372 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.96
Solubility : 0.00391 mg/ml ; 0.000011 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.68

Safety of [ 123853-39-4 ]

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 [ 123853-39-4 ]

* 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 [ 123853-39-4 ]
  • Downstream synthetic route of [ 123853-39-4 ]

[ 123853-39-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 110962-94-2 ]
  • [ 123853-39-4 ]
YieldReaction ConditionsOperation in experiment
53% With benzyltriethylammonium bromide; potassium hydroxide In isopropyl alcohol at 80℃; Take 400g of intermediate II plus 2L isopropanol in three-necked flask and dissolved, and then followed by adding 30g potassium hydroxide and 10g of triethylbenzylammonium bromide, stirred and heated to reflux for 80°C 5 to 6 hours. After cooling to room temperature, filtration, the filtrate was concentrated under reduced pressure to dryness. The residue was added 2L of methylene chloride and 2L of water, stirred for 10 minutes, standing layer, the aqueous phase was added dropwise under ice-cooling dilute hydrochloric acid to adjust pH = 4.5, was stirred for one hour ice bath, suction filtered and the filter cake washed with purified water to pH = 7, after the cake was dried to give 260g, tested, HPLC purity of 96.11percent. (See Fig. 3).
In reaction flask 130g butyric clevidipine important crude intermediate and 650ml of ethyl acetate wad added, the mixture was stirred and heated to 40°C , maintained for 10 minutes, filtered hot and the filter cake was dried to give a pale yellow solid 122g, that is an important intermediate clevidipine butyrate. By HPLC purity of 99.09percent (see Figure 4), yield 93percent.The total yield of the preparation of the present invention obtained by the acid clevidipine important intermediates 53percent.
1.43 kg
Stage #1: With tetra-(n-butyl)ammonium iodide In isopropyl alcohol at 20℃; for 4 h; Industrial scale
Stage #2: With hydrogenchloride In water at 20℃; for 2 h; Industrial scale
A mixture of 2,3-dichlorobenzaldehyde (0.9 kg, 5.14 mol), methyl acetoacetate (0.6 kg, 5.14 mol) and cyanoethyl 3-aminocrotonate (0.88 kg, 5.71 mol) Mol), pyridine (22g, 0.28mol) was added to isopropanol (15 L) and reacted at 80 ° C for 10 h. Cooling the temperature, filtering to obtain solid, the obtained solid by adding isopropyl alcohol (5L) recrystallization, filtration to get compound 3-(2-cyanoethyl) 5-methyl 4-(2',3'-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (1.8kg, 4.37mol). Compound III (1.8kg, 4.37mol) Was dissolved in isopropanol (20L) 1M Bu4NI 5.24L (5.2mol) solution was added at room temperature Stir for 4 h, The solvent was evaporated and addedWater (18 L), dilute hydrochloric acid(1M) at 20 ° C adjusted PH5-6, And stirred at this temperature for 2h, a yellow precipitate formation,Filtration was solid 1. 43kg,Yield: 78.0percent (based on 2,3-dichlorobenzaldehyde).
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 8, p. 1579 - 1589
[2] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 108 - 116
[3] Patent: CN105367487, 2016, A, . Location in patent: Paragraph 0021
[4] Patent: CN103242220, 2016, B, . Location in patent: Paragraph 0040; 0051-0052
  • 2
  • [ 74073-22-6 ]
  • [ 123853-39-4 ]
YieldReaction ConditionsOperation in experiment
91.32%
Stage #1: at 35 - 40℃; Reflux; Large scale
Stage #2: With sodium hydroxide In isopropyl alcoholLarge scale
The 3-amino-crotonic acid cyanogen ethyl ester 1.0 kg (6.49mol) inputs 5.5L isopropanol, inputs under stirring 2,3- two chlorine Asia phenmethyl acetyl methyl acetate 2.0 kg (7.32mol), heating to reflux reaction 6-8h, after the reaction is ended cooling to 35-45°C, inputs potassium hydroxide 550.0g (9.80mol), preserving heat and stirring 2-4h, subsequently inputs 60.0g activated carbon decolourizations 5-15min, filtering, filtrates in 30-40 °C dropwise 1mol/L hydrochloric acid solution to adjust pH value to 5-6, filtering, 40-50 °C decompression drying to obtain the intermediate-4 - (2,3-dichlorophenyl) - 1,4-dihydro -2,6-dimethyl-5-methoxy carbonyl-3-pyridine carboxylic acid 2.11 kg, yield 91.32percent.
Reference: [1] Patent: CN105461619, 2016, A, . Location in patent: Paragraph 0065; 0066; 0067
  • 3
  • [ 91189-59-2 ]
  • [ 123853-39-4 ]
YieldReaction ConditionsOperation in experiment
20% With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In methanol at 70℃; Reflux To about 1.03g 2.8mmol S13 compound prepared above was dissolved in 15mL of methanol was added Into approximately 260mg of 1.14mmol TEBAc a concentration of 40percent NaOH 2.5mL, at 70 ° C Under stirring at reflux, the reaction overnight, the methanol was removed by rotary evaporation, diluted with water, 2mol / L hydrochloric PH is 2-3 to the reaction system in the precipitated solid was filtered to give the product S14200mg, yield To 20percent,
Reference: [1] Patent: CN102464608, 2016, B, . Location in patent: Paragraph 0214; 0216
  • 4
  • [ 74073-26-0 ]
  • [ 123853-39-4 ]
YieldReaction ConditionsOperation in experiment
75.2% With trifluoroacetic acid In dichloromethane at 20℃; for 2.5 h; 4-(2,3-dichlorophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate-(tert-butyl) methylester(1) (412 mg, 1mmol) dissolved in dichloromethane (10 ml), by adding trifluoroacetic acid (1.5mmol), 20 °C stirring 2.5h, turns on lathe does solvent, cyclohexane and a small amount of ethyl acetate is added, solid precipitation, filtration, a small amount of cold ethyl acetate filter cake washing, drying, the obtained product (IV) 267 mg, yield 75.2percent (to 1 parts).
Reference: [1] Patent: CN103242221, 2016, B, . Location in patent: Paragraph 0045; 0046; 0047; 0049
[2] Patent: WO2012/69989, 2012, A1, . Location in patent: Page/Page column 5
  • 5
  • [ 5394-63-8 ]
  • [ 6334-18-5 ]
  • [ 14205-39-1 ]
  • [ 138279-32-0 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: WO2011/130852, 2011, A1, . Location in patent: Page/Page column 6
  • 6
  • [ 6334-18-5 ]
  • [ 123853-39-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 8, p. 1579 - 1589
[2] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 108 - 116
[3] Patent: CN102464608, 2016, B,
[4] Patent: CN103242220, 2016, B,
  • 7
  • [ 74073-22-6 ]
  • [ 123853-39-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 108 - 116
[2] Patent: CN103242221, 2016, B,
[3] Patent: CN103242221, 2016, B,
[4] Patent: CN103242221, 2016, B,
  • 8
  • [ 105-45-3 ]
  • [ 123853-39-4 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 1, p. 108 - 116
[2] Patent: CN103242220, 2016, B,
  • 9
  • [ 14205-39-1 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: CN103242221, 2016, B,
  • 10
  • [ 14205-39-1 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: CN103242221, 2016, B,
  • 11
  • [ 14205-39-1 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: CN103242221, 2016, B,
  • 12
  • [ 14205-39-1 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: CN103242221, 2016, B,
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