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[ CAS No. 106635-81-8 ] {[proInfo.proName]}

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Chemical Structure| 106635-81-8
Chemical Structure| 106635-81-8
Structure of 106635-81-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 106635-81-8 ]

CAS No. :106635-81-8 MDL No. :MFCD00892249
Formula : C28H34F3N3O7 Boiling Point : -
Linear Structure Formula :- InChI Key :CQBKFGJRAOXYIP-UHFFFAOYSA-N
M.W : 581.58 Pubchem ID :163761
Synonyms :
WR 238605 Succinate

Calculated chemistry of [ 106635-81-8 ]

Physicochemical Properties

Num. heavy atoms : 41
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.39
Num. rotatable bonds : 13
Num. H-bond acceptors : 12.0
Num. H-bond donors : 4.0
Molar Refractivity : 147.34
TPSA : 153.23 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -8.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.63
Log Po/w (XLOGP3) : 2.38
Log Po/w (WLOGP) : 6.81
Log Po/w (MLOGP) : 2.22
Log Po/w (SILICOS-IT) : 5.5
Consensus Log Po/w : 4.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.38
Solubility : 0.0245 mg/ml ; 0.0000421 mol/l
Class : Moderately soluble
Log S (Ali) : -5.24
Solubility : 0.00336 mg/ml ; 0.00000577 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -8.69
Solubility : 0.00000118 mg/ml ; 0.000000002 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.54

Safety of [ 106635-81-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 106635-81-8 ]

* 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.

  • Downstream synthetic route of [ 106635-81-8 ]

[ 106635-81-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 110-15-6 ]
  • [ 106635-80-7 ]
  • 8-[(4-Amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline succinate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In IMS; for 0.5h;Heating / reflux;Product distribution / selectivity; A stirred mixture of the product from Example 1.2 (159. 0g, 0. 27mol) and hydrazine hydrate (26.2 mL, 0. 51 mol, ) in ethanol (1. 35L) was heated under reflux for 7 hours. The mixture was cooled to 80C and 1.7M aqueous potassium hydroxide solution (0.8L) was added. The mixture was cooled to 39C and tert-butyl methyl ether (1.35L) was added. The mixture was cooled to 26C and the two phases were separated. The organic phase was washed with 1.7M aqueous potassium hydroxide solution (0.8L) and brine (475mL) and evaporated under reduced pressure. The residue was dissolved in IMS (475mL), succinic acid (41.3g, 0. 35mol) was added and the stirred mixture was heated under reflux for 30 minutes. The hot solution was filtered through Celite under vacuum and the filter was washed with hot IMS (160 ml). The filtrate and washings were combined, allowed to cool to 35C and seeded with <strong>[106635-80-7]tafenoquine</strong> crystals (0. 1 g). The mixture was cooled to 5C over 30 minutes and stirred at 0-5C for 1.5 hours. The product was isolated by filtration, washed with cold IMS (2 x 160 ml) and dried at 45-50C under reduced pressure for 2 days to give final product (115. 0g, 74%, purity 98.56%).
In ethanol; at 0 - 20℃; for 0.5h;Heating / reflux;Product distribution / selectivity; A mixture of the product from example 2.2 (7. 5g, 15.2 mmol), ethanol (150ml) and 5% Pd-C (2g) was stirred under ca. lbar hydrogen for 24 hours at ambient temperature. The catalyst was filtered off and the solvent evaporated to leave a volume of ca. 25ml. Succinic acid (2.3g, 19.8 mmol) was added, and the mixture heated under reflux for 30 minutes. The solution was then cooled to 0-5C, seeded with authentic target compound, and stirred for 2 hours. The crystalline product was filtered off, washed with ethanol (15ml) and dried in vacuo at 50C for 24 hours to give 8- [ (4-amino-l-methylbutyl) amino] -2,6-dimethoxy-4-methyl- 5- (3-trifluoromethylphenoxy) quinoline succinate as an off-white crystalline solid (6. 0g, 68%). A portion of the product (4. 0g) was recrystallised from ethanol (15ml). The crystalline product was filtered off, washed with ethanol (5ml) and dried in vacuo at 50C for 24 hours to give the product as an off-white crystalline solid (3.2g, 80% recovery). 1H NMR (d6-DMSO) 8 1.07 (d, 3H, CH3), 1.49 (m, 4H, CH2CH2), 2.09 (s, 3H, CH3-Ar), 2.27 (s, 4H, succinate), 2.66 (t, 2H, CH2-N), 3.57 (s, 3H, CH3-OAr), 3.60 (m, 1H, CH-N), 3.76 (s, 3H, CH3-OAr), 5.66 (d, 1H, NH), 6.49 (s, 1H, arom H), 6.56 (s, 1H, arom H), 6.79 (d, 1H, arom H), 6.84 (s, 1H, arom H), 7.11 (d, 1H, arom H), 7.29 (dd, 1H, arom H). MS m/z 463 (M+ of free base) Calc: C 57. 82 H 5. 89 N 7. 23 Found: C 57. 66 H5. 87 N7. 14
YieldReaction ConditionsOperation in experiment
9.IV IV IV 8-[(4-Amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline succinate A 50 ml, three necked round bottom flask equipped with a magnetic stirrer, condenser and thermowatch was charged with 8-[(4-phthalimido-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifiuoromethylphenoxy)quinoline (16) (1.186 g, 2 mmoles), 95% ethanol (12 ml) and hydrazine monohydrate (0.425 g, 8.5 mmoles. The reaction was refluxed for 30 minutes, then a large amount of solid formed (phthalhydrazide). Ethanol (8 ml) was added to dilute the reaction and this was refluxed for an additional 30 minutes. HPLC showed the reaction was complete, so the heat was removed and the reaction cooled to 20-25° C. The solid was removed by suction filtration and washed with ethanol (4*5 ml). The combined ethanol solution was concentrated to dryness using a rotary evaporator to give 0.9 g of crude title compound as the free base. This crude product was dissolved in methylene chloride (50 ml) and washed twice with 25 ml of 25% potassium hydroxide solution and washed once with 25 ml of water. The organic layer was dried over magnesium sulfate and concentrated to dryness using a rotary evaporator. The residue was dissolved in acetonitrile (5 ml) and a warm solution containing succinic acid (0.23 g, 2.3 mmoles), methanol (0.5 ml) and acetonitrile (5 ml) was added. The resulting solution was stirred and allowed to cool to room temperature and held for about 3-4 hours. The product was removed by suction filtration, washed with acetonitrile (5 ml) and air dried. Yield of off-white solid was 0.72 g (61.9%), mp=146-149° C. 1H-NMR(DMSOd6): δ 8.45 (4, br singlet, exchanges with D2O, NH2 and COOH), 7.6-6.8 (4, multiplet, phenoxy ring), 7.15 (1, s, C-7), 6.80 (1, s, C-3), 4.03(3, s, C-6 OCH3), 3.85 (3, s, C-3 OCH3), 3.2-2.6 (2, br multiplet, C-1 of side chain), 2.55 (3, s, CH3), 2,0-1.5 (4, br multiplet, C-2 and C-3 of side-chain), 1.33 (3, d, CH3 of side chain).
  • 3
  • 8-[(4-Amino-1-methylbutyl)amino]-2,6-dimethoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline succinate [ No CAS ]
  • [ 106635-80-7 ]
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