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[ CAS No. 1670-82-2 ] {[proInfo.proName]}

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Chemical Structure| 1670-82-2
Chemical Structure| 1670-82-2
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Product Details of [ 1670-82-2 ]

CAS No. :1670-82-2 MDL No. :MFCD00210441
Formula : C9H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GHTDODSYDCPOCW-UHFFFAOYSA-N
M.W : 161.16 Pubchem ID :595230
Synonyms :

Calculated chemistry of [ 1670-82-2 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 45.26
TPSA : 53.09 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) : -6.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.95
Log Po/w (XLOGP3) : 1.57
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 1.08
Log Po/w (SILICOS-IT) : 1.89
Consensus Log Po/w : 1.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.32
Solubility : 0.776 mg/ml ; 0.00482 mol/l
Class : Soluble
Log S (Ali) : -2.3
Solubility : 0.817 mg/ml ; 0.00507 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.65
Solubility : 0.364 mg/ml ; 0.00226 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.09

Safety of [ 1670-82-2 ]

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

Application In Synthesis of [ 1670-82-2 ]

* 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 [ 1670-82-2 ]
  • Downstream synthetic route of [ 1670-82-2 ]

[ 1670-82-2 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 50820-65-0 ]
  • [ 1670-82-2 ]
YieldReaction ConditionsOperation in experiment
95% With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water (c)
A solution of methyl indole-6-carboxylate (11.0 g) in a mixture of tetrahydrofuran (150 ml), methanol (150 ml), and water (63 ml) was treated with lithium hydroxide monohydrate (15.8 g).
The mixture was stirred at 60° C. for 6 hours and then concentrated to remove the organic solvents.
The residue was dissolved in water, and the solution was acidified with 50percent (v/v) hydrochloric acid.
The precipitate which formed was collected by filtration and dried to give indole-6-carboxylic acid (9.6 g, 95percent) as a tan powder; mp 253°-254°: NMR (80 MHz; CDCl3) 6.51(m, 1H, H3 -indole), 8.04(m, 1H, H7 -indole), 11.43(broad s, 1H, NH), 12.42(broad s, 1H, OH).
95% With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water (c)
A solution of methyl indole-6-carboxylate (11.0 g) in a mixture of tetrahydrofuran (150 ml), methanol (150 ml), and water (63 ml) was treated with lithium hydroxide monohydrate (15.8 g).
The mixture was stirred at 60°C for 6 hours and then concentrated to remove the organic solvents.
The residue was dissolved in water, and the solution was acidified with 50percent (v/v) hydrochloric acid.
The precipitate which formed was collect by filtration and dried to give indole-6-carboxylic acid (9.6 g, 95percent) as a tan powder; mp 253-254°; NMR (80 MHz; CDCl3): 6.51(m, 1H, H3-indole), 8.04(m, 1H, H7-indole), 11.43(broad s, 1H, NH), 12.42(broad s, 1H, OH).
88%
Stage #1: With lithium hydroxide; water In tetrahydrofuran at 80℃; for 16 h;
Stage #2: With hydrogenchloride In water
Step 1: Lithium hydroxide (0.72 g, 17.2 mmol, 3 equiv.) in water (10 mL) was added to methyl indole-6-carboxylate (1 g, 5.7 mmol, 1 equiv.) in tetrahydrofuran (10 mL) and the mixture stirred at 80° C. for 16 hours. The solution was concentrated under vacuum then diluted with dichloromethane (10 mL) and the organic layer extracted with water (3.x.10 mL). The aqueous phase was acidified to pH<1 with concentrated HCl forming a precipitate. The precipitate was filtered and washed with 1 M aqueous HCl (3.x.10 mL) to afford 1H-indole-6-carboxylic acid as a white solid, 0.807 g (88percent yield). LC (at)215 nm; Rt 1.02: 100percent, m/z (ES+): 162 (M+H+.); δH (400 MHz; MeOD) 8.15 (1H, d), 7.72 (1H, m), 7.67 (1H, m), 7.45 (1H, m), 6.53 (1H, m).
85%
Stage #1: With water; lithium hydroxide In methanol for 1 h; Reflux
Stage #2: With hydrogenchloride In water
To a solution of methyl indole-6-carboxylate (3.0 g) in MeOH (34 mL), a 3M aqueous solution of LiOH (17 mL, 3.0 equiv.) was added. The reaction mixture was heated at reflux for 1 Hr, then cooled at 0°C, diluted with water (50 mL) and acidified with HCl 12M (5 mL). The mixture was extracted with AcOEt (3*30 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4 and concentrated to give the product as a yellow solid (2.3 g, 85percent). M/Z (M+H)+ = 162.
57%
Stage #1: With lithium hydroxide monohydrate; water In tetrahydrofuran; methanol at 60℃;
Stage #2: With hydrogenchloride In water
Step 4.
1H-Indole-6-carboxylic acid
A solution of methyl 1H-indole-6-carboxylate (1.3 g, 7.43 mmol, 1.00 equiv) in tetrahydrofuran (20 mL) was placed into a 250-mL round-bottom flask.
Then CH3OH (20 mL), H2O (10 mL), LiOH.H2O (1.9 g, 45.24 mmol, 6.09 equiv) were added.
The resulting solution was stirred overnight at 60° C.
The resulting mixture was concentrated in vacuo, and diluted with water.
The resulting solution was extracted with 2*100 mL of ether and the aqueous layers were combined.
The pH value of the solution was adjusted to pH 3 with hydrochloric acid, and the solids were collected by filtration.
This resulted in 0.68 g (57percent) of 1H-indole-6-carboxylic acid as a light yellow solid.

Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 6819 - 6843
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439
[3] Patent: US4898863, 1990, A,
[4] Patent: EP242167, 1991, B1,
[5] Patent: US2007/60567, 2007, A1, . Location in patent: Page/Page column 19
[6] Patent: EP2210891, 2010, A1, . Location in patent: Page/Page column 72
[7] Patent: US2012/277224, 2012, A1, . Location in patent: Page/Page column 84
[8] European Journal of Medicinal Chemistry, 2017, vol. 136, p. 393 - 405
  • 2
  • [ 106851-27-8 ]
  • [ 1670-82-2 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 15, p. 1653 - 1656
  • 3
  • [ 93247-78-0 ]
  • [ 1670-82-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 17, p. 6819 - 6843
  • 4
  • [ 7356-11-8 ]
  • [ 1670-82-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439
[2] Patent: US2012/277224, 2012, A1,
  • 5
  • [ 104447-80-5 ]
  • [ 1670-82-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 13, p. 2419 - 2439
[2] Patent: US2012/277224, 2012, A1,
  • 6
  • [ 14719-83-6 ]
  • [ 1670-82-2 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 15, p. 1653 - 1656
  • 7
  • [ 106851-22-3 ]
  • [ 1670-82-2 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 15, p. 1653 - 1656
  • 8
  • [ 106867-41-8 ]
  • [ 1670-82-2 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 15, p. 1653 - 1656
  • 9
  • [ 96-98-0 ]
  • [ 1670-82-2 ]
Reference: [1] Patent: US2012/277224, 2012, A1,
  • 10
  • [ 15861-36-6 ]
  • [ 1670-82-2 ]
Reference: [1] Journal of the Chemical Society, 1924, vol. 125, p. 2288
  • 11
  • [ 1670-82-2 ]
  • [ 74-88-4 ]
  • [ 1204-32-6 ]
Reference: [1] Patent: US2003/92728, 2003, A1,
[2] Patent: WO2005/30704, 2005, A1, . Location in patent: Page/Page column 199-200
[3] Patent: US2014/194386, 2014, A1, . Location in patent: Paragraph 0495
  • 12
  • [ 1670-82-2 ]
  • [ 1196-70-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 9, p. 3725 - 3732
  • 13
  • [ 1670-82-2 ]
  • [ 494799-17-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 19, p. 4987 - 4993
[2] Patent: US2008/188458, 2008, A1,
[3] Patent: US2008/171015, 2008, A1,
[4] Patent: US2008/226592, 2008, A1,
  • 14
  • [ 1670-82-2 ]
  • [ 851211-74-0 ]
Reference: [1] Journal of Chemical Research, 2015, vol. 39, # 5, p. 296 - 299
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