Home Cart 0 Sign in  
X

[ CAS No. 677304-69-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 677304-69-7
Chemical Structure| 677304-69-7
Chemical Structure| 677304-69-7
Structure of 677304-69-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 677304-69-7 ]

Related Doc. of [ 677304-69-7 ]

Alternatived Products of [ 677304-69-7 ]

Product Details of [ 677304-69-7 ]

CAS No. :677304-69-7 MDL No. :MFCD06804572
Formula : C8H6N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :WBCWIQCXHSXMDH-UHFFFAOYSA-N
M.W : 162.15 Pubchem ID :12639205
Synonyms :

Calculated chemistry of [ 677304-69-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.05
TPSA : 65.98 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.74
Log Po/w (XLOGP3) : 1.08
Log Po/w (WLOGP) : 1.26
Log Po/w (MLOGP) : 0.72
Log Po/w (SILICOS-IT) : 1.38
Consensus Log Po/w : 1.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.01
Solubility : 1.57 mg/ml ; 0.00967 mol/l
Class : Soluble
Log S (Ali) : -2.06
Solubility : 1.42 mg/ml ; 0.00876 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.27
Solubility : 0.863 mg/ml ; 0.00532 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.29

Safety of [ 677304-69-7 ]

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 [ 677304-69-7 ]

* 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 [ 677304-69-7 ]
  • Downstream synthetic route of [ 677304-69-7 ]

[ 677304-69-7 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 755752-82-0 ]
  • [ 677304-69-7 ]
YieldReaction ConditionsOperation in experiment
94% With potassium hydroxide In methanol; water at 0 - 20℃; for 18 h; A solution of the indazole (8.30 g, 33.0 mmol) in methanol (100 mL) at 0 C was treated with an 29percent aqueous solution of potassium hydroxide (20 mL). The reaction mixture was allowed to warm to rt and was maintained for 18 h. The pH of the solution was adjusted to 5.5 by the addition of concentrated hydrochloric acid and the volatiles were removed under reduced pressure. The residue was partitioned between brine (100 mL) and ethyl acetate (200 mL) and the aqueous layer was extracted with additional warm ethyl acetate (200 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated. The residue was triturated with ethyl acetate (30 mL) and the solids were isolated by filtration, thus providing 5.86 g (94percent) of the acid
55%
Stage #1: With potassium hydroxide; water In methanol at 0 - 20℃; Heating / reflux
Stage #2: With hydrogenchloride In methanol; water
A mixture of 2-amino-3-methylbenzoic acid (15.2 g, 0.10 mol), dimethylformamide (333 mL) and CsCO3 (49 g, 0.15 mol) was stirred at room temperature for about 40 minutes before drop wise addition of iodomethane (14.2 g, 6.2 mL, 0.10 mol) in dimethylformamide ("DMF") (115 mL). The mixture was stirred . at room temperature overnight. The mixture was diluted with water (1 L), and extracted with diethyl ether. The aqueous phase was back extracted with diethyl ether. The combined organic extracts were washed with saturated aqueous NaCI, dried over MgSO4, filtered and concentrated. The resultant material was dried at room temperature/0.5 mmHg to afford methyl 2-amino-3-methylbenzoate (17 g, 100percent).To a solution methyl 2-amino-3-methylbenzoate (16.5 g, 0.10 mol) in CHCI3 (286 mL) was added acetic anhydride (23.5 g, 21.7 mL, 0.23 mol) so as to maintain the internal temperature <40 0C. The mixture was stirred at room temperature for 1 hour before addition of potassium acetate (2.94 g, 30 mmol) and isoamyl nitrite (25.8 g, 30 mL, 0.22 mol). The resultant mixture was heated at reflux overnight. To this was then added methanol (94 mL) and 6 N HCI (94 mL) and the mixture was stirred overnight. The reaction mixture was concentrated to provide an orange solid which was subsequently triturated with ethyl <n="29"/>acetate and the solids were isolated by vacuum filtration. The solids were dried at room temperature/0.5 mmHg to afford methyl 1 H-indazole-7-carboxylate (15.4 g, 88percent). -A solution of methyl 1 H-indazole-7-carboxylate (14.96 g, 84.9 mmol) in methanol (180 ml_) was cooled to 0 0C before addition of 29percent aqueous potassium hydroxide (36 ml_). The ice bath was removed and the reaction mixture was stirred at room temperature overnight. The pH was adjusted to 5.5 using concentrated HCI. The volatiles were removed by vacuum filtration and the resultant material was suspended in water (100 mL) and ethyl acetate (200 mL). The resultant precipitate was isolated by vacuum filtration and rinsed with ethyl acetate. The solids were dried at room temperature/0.5 mmHg to afford the title compound (7.54 g, 55percent).
Reference: [1] Patent: WO2004/29050, 2004, A1, . Location in patent: Page 64;65
[2] Patent: WO2008/65508, 2008, A1, . Location in patent: Page/Page column 27-28
  • 2
  • [ 677304-71-1 ]
  • [ 677304-69-7 ]
YieldReaction ConditionsOperation in experiment
94%
Stage #1: With potassium hydroxide; water In methanol at 0 - 20℃; for 18 h;
Stage #2: With hydrogenchloride In methanol; water
To a solution of 2-amino-3-methylbenzoic acid (66.9 mmol) in N, N-dimethylformamide (200 mL) was added cesium carbonate (102 mmol). The mixture was stirred for 30 min. A solution of methyl iodide (67.0 mmol) in NN-dimethylformamide (50 mL) was added dropwise and the reaction mixture was maintained for 18 h at rt. The reaction mixture was partitioned between water (1 L) and ether (200 mL) and the water layer was extracted with an additional volume of ether (100 mL). The combined extracts were washed with brine (500 mL), dried over anhydrous potassium carbonate, and concentrated, thus providing methyl 2-amino-3-methylbenzoate in 92percent yield.'H NMR (400 MHz, CDC13) 6 7.77 (d, 1H), 7.19 (d, 1H), 6.59 (t, 1H), 5.82 (bs, 2H), 3.86 (s, 3H), 2.17 (s, 3H). To a solution of the ester (106 mmol) in chloroform (300 mL) was added acetic anhydride (239 mmol) while maintaining the temperature below 40 °C. The reaction mixture was maintained at room temperature for 1 h when potassium acetate (30.6 mmol) and isoamyl nitrite (228 mmol) was added. The reaction mixture was heated at reflux for 24 h and was allowed to cool to room temperature. The reaction mixture was washed with a saturated, aqueous solution of sodium bicarbonate, dried over sodium sulfate, and concentrated. Methanol (100 mL) and 6 N hydrochloric acid (100 mL) were added to the residue and the mixture was maintained for 18 h at rt. The volatiles were removed under reduced pressure and the residue was triturated with ethyl acetate (100 mL). The product was isolated by filtration, washed with ethyl acetate (20 mL), and dried, thus providing methyl 1H-indazole-7-carboxylate hydrochloride in 68percent yield.'H NMR (500 MHz, Me2SO-d6) 8 13.3 (bs, 1H), 8.26 (d, 1H), 8.12 (d, 1H), 8.25 (dd, 1H), 7.27 (t, 1H), 3.97 (s, 3H); MS (APCI) m/z 177 (M++1). A solution of the indazole (33.0 mmol) in methanol (100 mL) at 0 °C was treated with an 29percent aqueous solution of potassium hydroxide (20 mL). The reaction mixture was allowed to warm to rt and was maintained for 18 h. The pH of the solution was adjusted to 5.5 by the addition of concentrated hydrochloric acid and the volatiles were removed under reduced pressure. The residue was partitioned between brine (100 mL) and ethyl acetate (200 mL) and the aqueous layer was extracted with additional warm ethyl acetate (200 mL). The combined organic extracts were dried over anhydrous sodium sulfate and concentrated. The residue was triturated with ethyl acetate (30 mL) and the solids were isolated by filtration, thus providing the acid in 94percent yield.
Reference: [1] Patent: WO2005/92890, 2005, A2, . Location in patent: Page/Page column 77-79
  • 3
  • [ 22223-49-0 ]
  • [ 677304-69-7 ]
Reference: [1] Patent: US2005/20611, 2005, A1, . Location in patent: Page/Page column 44
[2] Patent: WO2008/65508, 2008, A1,
  • 4
  • [ 256228-64-5 ]
  • [ 677304-69-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 11, p. 5962 - 5973
  • 5
  • [ 4389-45-1 ]
  • [ 677304-69-7 ]
Reference: [1] Patent: WO2008/65508, 2008, A1,
  • 6
  • [ 37619-23-1 ]
  • [ 677304-69-7 ]
Reference: [1] Patent: WO2008/65508, 2008, A1,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 677304-69-7 ]

Carboxylic Acids

Chemical Structure| 1031417-41-0

[ 1031417-41-0 ]

7-Methyl-1H-indazole-5-carboxylic acid

Similarity: 0.97

Chemical Structure| 73907-95-6

[ 73907-95-6 ]

6-Amino-1H-indazole-7-carboxylic acid

Similarity: 0.96

Chemical Structure| 61700-61-6

[ 61700-61-6 ]

1H-Indazole-5-carboxylic acid

Similarity: 0.91

Chemical Structure| 704-91-6

[ 704-91-6 ]

1H-Indazole-6-carboxylic acid

Similarity: 0.91

Chemical Structure| 787580-93-2

[ 787580-93-2 ]

3-Oxo-2,3-dihydro-1H-indazole-5-carboxylic acid

Similarity: 0.88

Related Parent Nucleus of
[ 677304-69-7 ]

Indazoles

Chemical Structure| 1031417-41-0

[ 1031417-41-0 ]

7-Methyl-1H-indazole-5-carboxylic acid

Similarity: 0.97

Chemical Structure| 73907-95-6

[ 73907-95-6 ]

6-Amino-1H-indazole-7-carboxylic acid

Similarity: 0.96

Chemical Structure| 755752-82-0

[ 755752-82-0 ]

Methyl 1H-indazole-7-carboxylate

Similarity: 0.93

Chemical Structure| 61700-61-6

[ 61700-61-6 ]

1H-Indazole-5-carboxylic acid

Similarity: 0.91

Chemical Structure| 704-91-6

[ 704-91-6 ]

1H-Indazole-6-carboxylic acid

Similarity: 0.91