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[ CAS No. 202745-73-1 ] {[proInfo.proName]}

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Chemical Structure| 202745-73-1
Chemical Structure| 202745-73-1
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Product Details of [ 202745-73-1 ]

CAS No. :202745-73-1 MDL No. :MFCD08690250
Formula : C10H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DJQOGNYSBOIJKE-UHFFFAOYSA-N
M.W : 175.18 Pubchem ID :19819261
Synonyms :

Calculated chemistry of [ 202745-73-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 50.16
TPSA : 42.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.53
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 1.38
Log Po/w (SILICOS-IT) : 1.3
Consensus Log Po/w : 1.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.34
Solubility : 0.808 mg/ml ; 0.00461 mol/l
Class : Soluble
Log S (Ali) : -2.03
Solubility : 1.65 mg/ml ; 0.00943 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.21
Solubility : 1.07 mg/ml ; 0.0061 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 202745-73-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 202745-73-1 ]

* 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 [ 202745-73-1 ]
  • Downstream synthetic route of [ 202745-73-1 ]

[ 202745-73-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 1204-32-6 ]
  • [ 202745-73-1 ]
YieldReaction ConditionsOperation in experiment
99% With methanol; sodium hydroxide; water In tetrahydrofuran at 20℃; for 36 h; Step 2: 1-Methyl-lH-indole-6-carboxylic acid (167) [0334] Methyl 1-METHYL-LH-INDOLE-6-CARBOXYLATE 166 (1.24 MMOL) was stirred with sodium hydroxide (0.59g, 14.88 MMOL) in a 2: 2: 1 mixture of methanol/THF/water (7.5 mL) for 36 hrs at rt to form a precipitate which was collected by filtration and LYOPHILIZED overnight to give the title compound 167 (0.54g, 99percent yield). MS: 175.06 (CALC), 176.1 (OBS).
86%
Stage #1: With lithium hydroxide In tetrahydrofuran; methanol; water; acetonitrile at 20℃;
Stage #2: With hydrogenchloride In water
To N-methylindole-6-carboxylic acid methyl ester in 3 mL 1 :1:1 :1 acetonitrile/THF/water/MeOH was added LiOH and allowed to stir at room temperature over the weekend. The reaction mixture was concentrated under reduced pressure before adding EtOAc and water. The organic phase was separated and the water acidified with 1N HCI and extracted into EtOAc (3x50 mL), washed with water, saturated aqueous NaCI1 dried over MgSO4, filtered, and concentrated under reduced pressure. The material was dried under reduced pressure to afford the title product (0.16 g, 86percent).
Reference: [1] Patent: WO2005/30704, 2005, A1, . Location in patent: Page/Page column 199-200
[2] Patent: WO2008/65508, 2008, A1, . Location in patent: Page/Page column 32
[3] Heterocycles, 2006, vol. 67, # 2, p. 643 - 653
  • 2
  • [ 20996-87-6 ]
  • [ 202745-73-1 ]
Reference: [1] Patent: US5856517, 1999, A,
[2] Patent: EP915872, 2003, B1,
  • 3
  • [ 124-38-9 ]
  • [ 202745-73-1 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 47, p. 11168 - 11176
  • 4
  • [ 155868-51-2 ]
  • [ 202745-73-1 ]
Reference: [1] Tetrahedron, 2005, vol. 61, # 47, p. 11168 - 11176
  • 5
  • [ 202745-74-2 ]
  • [ 202745-73-1 ]
Reference: [1] Heterocycles, 2006, vol. 67, # 2, p. 643 - 653
  • 6
  • [ 50820-65-0 ]
  • [ 202745-73-1 ]
Reference: [1] Heterocycles, 2006, vol. 67, # 2, p. 643 - 653
  • 7
  • [ 50820-64-9 ]
  • [ 202745-73-1 ]
Reference: [1] Heterocycles, 2006, vol. 67, # 2, p. 643 - 653
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