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[ CAS No. 282526-98-1 ] {[proInfo.proName]}

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Chemical Structure| 282526-98-1
Chemical Structure| 282526-98-1
Structure of 282526-98-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 282526-98-1 ]

CAS No. :282526-98-1 MDL No. :MFCD09839697
Formula : C25H39NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :MVCQKIKWYUURMU-UHFFFAOYSA-N
M.W : 401.58 Pubchem ID :9952916
Synonyms :
ATL-962

Calculated chemistry of [ 282526-98-1 ]

Physicochemical Properties

Num. heavy atoms : 29
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.68
Num. rotatable bonds : 16
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 123.84
TPSA : 52.33 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 : Yes
Log Kp (skin permeation) : -1.8 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.79
Log Po/w (XLOGP3) : 9.79
Log Po/w (WLOGP) : 7.36
Log Po/w (MLOGP) : 5.2
Log Po/w (SILICOS-IT) : 8.25
Consensus Log Po/w : 7.28

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -7.7
Solubility : 0.00000807 mg/ml ; 0.0000000201 mol/l
Class : Poorly soluble
Log S (Ali) : -10.81
Solubility : 0.0000000062 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -9.75
Solubility : 0.0000000721 mg/ml ; 0.0000000002 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.44

Safety of [ 282526-98-1 ]

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 [ 282526-98-1 ]

* 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 [ 282526-98-1 ]
  • Downstream synthetic route of [ 282526-98-1 ]

[ 282526-98-1 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 890655-08-0 ]
  • [ 282526-98-1 ]
YieldReaction ConditionsOperation in experiment
96.5% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; In a 3L three-mouth flask, disperse the compound C (120g) in 2L dichloromethane. Under stirring add EDCI (82.24g). The reaction was stirred at room temperature.TLC (n-hexane: ethyl acetate: acetic acid = 50:1:0.1) monitored the progress of the reaction, the reaction was complete after washing 3 times × 700mL, the organic layer was separated, 12g of activated carbon was added and refluxed for 20min, cooled to room temperature activated carbon was filtered off , concentrated under reduced pressure to remove methylene chloride, the crude product was dispersed in 575mL of acetonitrile, stirred at room temperature for 1 hour to fully disperse the substrate, an ice-water bath (0-10 deg.C) was stirred for 3 hours, filtration, 40 deg.C blast drying, a white solid 110.8g. Yield 96.5percent.
92% With 1,1'-carbonyldiimidazole In dichloromethane 2-(hexadecyloxycarbonyl)-amino-5-methyl benzoic acid (21 g, 0.05 mol) was placed in a 1 L reaction flask, and 600 ml of dichloromethane was added thereto. CDI (8.1g, 0.05 mol) and DMPA (1g) was added with stirring, followed by the reaction overnight. the reaction solution was then washed thoroughly in sequence with 1percent hydrochloric acid and water under stirring. After liquid separation and concentration by removal most of dichloromethane, 100 ml of n-heptane was then added under ice bath and stirred for 2h. After suction filtration and drying, 18.5 g of cetilistat was obtained, in a yield of 92percent, purity ≥99. 5percent, single impurity <= 0.1percent.
85.5% at 0 - 10℃; for 1 h; To the embodiment 1 in the upper electrode reaction 4 recovery of pyridine 33 ml, temperature control 0-5°C, subsequently slowly instillment chlorine formic acid ethyl ester (10.7g, 99mmol, 5.0eq), control the inner is situated between warm 0-10°C, preserving heat and stirring 1 hour, at this moment the normalized content he west for favorable department 98.86percent.Reaction is ended, into the water 18 ml and recovery and two chlorodifluoromethane 18 ml, violent stirring 10 minutes, then left standstill, divide the liquid. Organic reinforced with 30mL1mol/L thin salt acid washing 2 times, then the purified water for washing to pH=6-7. Decompression of organic phase is concentrated to small volume, then the dichloromethane is replaced into the n-heptane is clean. And then concentrate under reduced pressure and to 15-20mL left and right, a large number of solid precipitation, filtration, 40-45°C, 0 . 098 MPa the lower vacuum drying, to obtain white solid powder 6.8g, total yield of 85.5percent, the purity is 99.63percent, the largest single impurity is 0.06percent. X-ray powder diffraction data as shown in table 2 is shown in, and Chinese Patent CN102482235 consistent.
85% at 20℃; for 3 h; Cooling with ice 66g of 2-(hexadecoxycarbonylamino)-5-methylbenzoic acid was suspended in 330mL of pyridine, and 45mL of ethyl chloroformate was added dropwise slowly under ice-cooling. After the addition was completed, the mixture was naturally raised to room temperature and reacted for 3h. After the reaction was completed, the reaction solution was poured into 700 mL of ice water, filtered, and the filter cake was dried to constant weight to give 56 g of a gray solid, which was 2-hexadecyloxy-6-methyl-4H-3,1-benzoxazin-4-one (cetilistat) in 85percent yield.
83.3%
Stage #1: With pyridine In dichloromethane at 25 - 30℃; for 0.166667 h;
Stage #2: With chloroformic acid ethyl ester In dichloromethane at 0 - 35℃; for 4 h;
2-Hexadecyloxycarbonylamino-5-methylbenzoic acid (10 g), pyridine (30 ml) and dichloromethane (150 ml) were taken into a reaction flask at 25-30°C and the resulting mass was stirred for 10 minutes at the same temperature. The resulting solution wascooled to 0-5°C and then ethyl chloroformate (10 ml) was added drop-wise at the same temperature. The resulting mass was stirred for 2 hours at 0-5°C. The temperature of reaction mass was raised to 25-35°C and then stirred for 2 hours at the same temperature. To the resulting mass, water (100 ml) was added at room temperature and then stirred for 15 minutes at the same temperature. The layers were separated and theorganic layer was distilled under vacuum up to 60°C to obtain a residue (weight: 10 g). To the resulting residue, ethyl acetate (50 ml) was added at room temperature, followed by heating the mass at 65°C to obtain a clear solution. To the resulting solution, activated carbon (2 g) was added at 65°C and then stirred for 10 minutes at the same temperature. The resulting mass was filtered and the filtrate was cooled to 0-5°C. Theseparated solid was filtered, washed with ethyl acetate (10 ml) and then dried for 8 hours at 50-55°C to produce 8 g of Cetilistat (Yield: 83.3percent, Purity by HPLC: 99.5percent).

Reference: [1] Patent: CN105669585, 2016, A, . Location in patent: Paragraph 0063; 0064; 0065
[2] Patent: CN103936687, 2016, B, . Location in patent: Paragraph 0080-0082
[3] Patent: CN105622539, 2016, A, . Location in patent: Paragraph 0058; 0059; 0060; 0061; 0062
[4] Patent: CN104341370, 2017, B, . Location in patent: Paragraph 0063; 0064; 0065
[5] Patent: WO2018/11676, 2018, A1, . Location in patent: Page/Page column 17; 18
[6] Patent: EP1669346, 2006, A1, . Location in patent: Page/Page column 13
[7] Patent: CN106366047, 2017, A, . Location in patent: Paragraph 0027-0032; 0033-0038; 0039-0042; 0043-0046
  • 2
  • [ 890655-08-0 ]
  • [ 541-41-3 ]
  • [ 282526-98-1 ]
Reference: [1] Patent: US2007/232825, 2007, A1,
  • 3
  • [ 36653-82-4 ]
  • [ 282526-98-1 ]
Reference: [1] Patent: CN105439974, 2016, A,
[2] Patent: WO2018/11676, 2018, A1,
  • 4
  • [ 26272-90-2 ]
  • [ 282526-98-1 ]
Reference: [1] Patent: CN105439974, 2016, A,
[2] Patent: CN105439974, 2016, A,
[3] Patent: CN105439974, 2016, A,
  • 5
  • [ 13784-52-6 ]
  • [ 282526-98-1 ]
Reference: [1] Patent: CN105439974, 2016, A,
  • 6
  • [ 2941-78-8 ]
  • [ 282526-98-1 ]
Reference: [1] Patent: CN103936687, 2016, B,
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