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[ CAS No. 123654-26-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 123654-26-2
Chemical Structure| 123654-26-2
Chemical Structure| 123654-26-2
Structure of 123654-26-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 123654-26-2 ]

CAS No. :123654-26-2 MDL No. :MFCD12923204
Formula : C9H8ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :KRMUVKSAOVLXLF-UHFFFAOYSA-N
M.W : 213.62 Pubchem ID :10632401
Synonyms :

Calculated chemistry of [ 123654-26-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.16
TPSA : 72.55 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.61 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.36
Log Po/w (XLOGP3) : 1.4
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.13
Log Po/w (SILICOS-IT) : 1.74
Consensus Log Po/w : 1.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.3
Solubility : 1.08 mg/ml ; 0.00504 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.634 mg/ml ; 0.00297 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.33
Solubility : 1.01 mg/ml ; 0.00471 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.11

Safety of [ 123654-26-2 ]

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 [ 123654-26-2 ]

* 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 [ 123654-26-2 ]
  • Downstream synthetic route of [ 123654-26-2 ]

[ 123654-26-2 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 143878-29-9 ]
  • [ 123654-26-2 ]
YieldReaction ConditionsOperation in experiment
89.8% at 90℃; for 8 h; The resulting intermediate 7 (30 g, 0.11 mol), water (150 mL),Propylene glycol monomethyl ether (36mL) and 50percent sodium hydroxide solution (90mL), slowly heated to 90 ° C with stirring, the same temperature for 8h, the reaction was monitored by TLC. After the reaction is completed,Cooled to 5 ° C with ice bath and stirred for 2h, filtered with suction,The filter cake was washed with an appropriate amount of water added to 500mL single-necked flask,Water (210 mL) and propylene glycol monomethyl ether (35 mL) were added,The temperature of the reaction solution was raised to 80 ° C and the reaction solution became homogeneous.Dilute dilute hydrochloric acid, adjust pH to about 3, precipitated solid.After cooling to 10 ° C, stirring was continued for 2h. Suction filtration,The filter cake was washed with an appropriate amount of water and dried to give an off-white solid,Yield 20.8g, yield 89.8percent, purity 99percent
Reference: [1] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 1, p. 42 - 52
[2] Patent: CN107337658, 2017, A, . Location in patent: Paragraph 0051; 0052
[3] Patent: WO2017/137910, 2017, A1,
  • 2
  • [ 124-38-9 ]
  • [ 123654-26-2 ]
YieldReaction ConditionsOperation in experiment
32.2% With n-butyllithium In tetrahydrofuran; hexane; water b)
To a cooled (-70° C.) and stirred mixture of 15.6 parts of a solution of n.butyllithium in hexane 2.5M and 44.5 parts of tetrahydrofuran was added dropwise a solution of 4 parts of intermediate 8 in 26.7 parts of tetrahydrofuran under a nitrogen flow.
The reaction mixture was stirred for 1 hour at about -60° C. and was poured into a saturated suspension of carbondioxide (ice) in 44.5 parts of tetrahydrofuran.
The whole was allowed to warm up to room temperature while being stirred and 80 parts of water were added.
The aqueous layer was neutralized with hydrochloric acid and the formed precipitate was filtered off and dried in vacuo at 60° C., yielding 1.1 parts (32.2percent) of 4-amino-5-chloro-2,3-dihydro-7-benzofurancarboxylic acid; mp. 258.4° C. (interm. 9).
In a similar manner there was also prepared:
Reference: [1] Patent: US5374637, 1994, A,
  • 3
  • [ 4093-28-1 ]
  • [ 123654-26-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 1, p. 42 - 52
[2] Patent: CN107337658, 2017, A,
  • 4
  • [ 202664-85-5 ]
  • [ 123654-26-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 1, p. 42 - 52
[2] Patent: WO2017/137910, 2017, A1,
  • 5
  • [ 149466-67-1 ]
  • [ 123654-26-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 1, p. 42 - 52
[2] Patent: WO2017/137910, 2017, A1,
  • 6
  • [ 91958-13-3 ]
  • [ 123654-26-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 1, p. 42 - 52
  • 7
  • [ 110751-41-2 ]
  • [ 123654-26-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 1, p. 42 - 52
  • 8
  • [ 202664-83-3 ]
  • [ 123654-26-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 1, p. 42 - 52
  • 9
  • [ 4136-97-4 ]
  • [ 123654-26-2 ]
Reference: [1] Patent: CN107337658, 2017, A,
  • 10
  • [ 65-49-6 ]
  • [ 123654-26-2 ]
Reference: [1] Patent: CN107337658, 2017, A,
  • 11
  • [ 24190-77-0 ]
  • [ 123654-26-2 ]
Reference: [1] Patent: CN107337658, 2017, A,
  • 12
  • [ 179474-79-4 ]
  • [ 123654-26-2 ]
  • [ 179474-81-8 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: With 1,1'-carbonyldiimidazole In tetrahydrofuran for 0.416667 h;
Stage #2: at 45 - 50℃; for 4 h;
THF, 4-amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid (1.0 g), a small amount of CDI was added, stirred for 25 min,(0.8 g, GC & gt; 98percent) was added dropwise to a solution of 1- (3-methoxypropyl) -4-piperidinamine (I) at 45 ° C for 4 h, (30g), precipitate a large amount of solid, stirring at 25 for 1h; pumping, 20g of water rinse, collecting filter cake, drying, diclofenac 1.5g , Yield 85percent (mp = 91-92 ° C).To the reaction flask was added paclitaxel (1.0 g) and 75percent ethanol (5 mL), heated to 40 ° C, and succinic acid (0.35 g) was added with stirring and stirred for 3 h. The filter cake was recrystallized from 75percent ethanol and dried to give 1.17 g of white granular crystals in 93percent yield
Reference: [1] Patent: CN106146386, 2016, A, . Location in patent: Paragraph 0068; 0069; 0070; 0071
  • 13
  • [ 123654-26-2 ]
  • [ 179474-81-8 ]
Reference: [1] Patent: WO2017/137910, 2017, A1,
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