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[ CAS No. 98549-88-3 ] {[proInfo.proName]}

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Chemical Structure| 98549-88-3
Chemical Structure| 98549-88-3
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Product Details of [ 98549-88-3 ]

CAS No. :98549-88-3 MDL No. :MFCD08272242
Formula : C7H6N2O Boiling Point : -
Linear Structure Formula :- InChI Key :VUQZKLXKFUBWRP-UHFFFAOYSA-N
M.W : 134.14 Pubchem ID :22030722
Synonyms :

Calculated chemistry of [ 98549-88-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 38.12
TPSA : 48.91 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) : -6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.98
Log Po/w (XLOGP3) : 0.96
Log Po/w (WLOGP) : 1.27
Log Po/w (MLOGP) : 0.37
Log Po/w (SILICOS-IT) : 1.59
Consensus Log Po/w : 1.04

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.94
Solubility : 1.53 mg/ml ; 0.0114 mol/l
Class : Very soluble
Log S (Ali) : -1.57
Solubility : 3.57 mg/ml ; 0.0266 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.3
Solubility : 0.668 mg/ml ; 0.00498 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.33

Safety of [ 98549-88-3 ]

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

Application In Synthesis of [ 98549-88-3 ]

* 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 [ 98549-88-3 ]
  • Downstream synthetic route of [ 98549-88-3 ]

[ 98549-88-3 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 858116-66-2 ]
  • [ 98549-88-3 ]
YieldReaction ConditionsOperation in experiment
78.5% With lithium hydroxide monohydrate; N,N′-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide; copper(II) acetylacetonate In water; dimethyl sulfoxide at 100℃; for 6 h; Inert atmosphere To a 50 ml reaction flask at room temperature, the compound of formula II (4.08 g, 11.5 mmol) was added, Copper acetylacetonate (0.15g, 0.575mmol), ΒΗΜΡO (0.15g, 0 · 575mmol), lithium hydroxide monohydrate (2 · 42g, 57.5mmol), 18ml of DMSO, 4.5ml of water, stirring was turned on, replaced with nitrogen, and the temperature was raised to an internal temperature of 100 °C. Temperature reaction for 6 hours. Control raw material reaction is over, stop heating, cool to room temperature (20-30 °C), add water 100ml, adjust PH to 6 with 2N dilute hydrochloric acid, precipitation of solids, suction filtration, aqueous phase with ethyl acetate 50ml * 3 Extraction, combining the organic phases, washing once with water and saturated aqueous sodium chloride solution, drying over anhydrous sodium sulfate, and concentrating the solvent to obtain the compound of formula III. Yield: 1.2 g, yield: 78.5percent.
Reference: [1] Patent: CN107434807, 2017, A, . Location in patent: Paragraph 0056-0059; 0080-0083; 0102-0106
  • 2
  • [ 928653-80-9 ]
  • [ 98549-88-3 ]
YieldReaction ConditionsOperation in experiment
66.2% With copper(l) iodide; N,N`-dimethylethylenediamine In water at 160℃; for 19 h; Inert atmosphere To a 50 ml suffocating tank at room temperature, the compound of Formula IV (4 g, 13.5 mmol), copper iodide (0.128 g, 0.675 mmol), DMEDA (0.06 g, 0.675 mmol), potassium phosphate (2. 86 g, 13 · 5 mmol), water 40 ml, stirring was started, the gas in the stifling tank was replaced with nitrogen, and the temperature was raised to an internal temperature of 160 °C, and the temperature was maintained for 19 hours. The control of the raw material reaction is over, the heating is stopped, the temperature is lowered to room temperature (20-30 °C), the pH is adjusted to 6 with 2N dilute hydrochloric acid, the aqueous phase is extracted with ethyl acetate 50 ml*3, and the organic phases are combined, respectively with water and The solution was washed once with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and the solvent was concentrated to give the compound of formula III. Yield: 1.2 g, yield: 66.2percent.
Reference: [1] Patent: CN107434807, 2017, A, . Location in patent: Paragraph 0069-0072; 0091-0094; 0013-0017
  • 3
  • [ 183208-36-8 ]
  • [ 98549-88-3 ]
YieldReaction ConditionsOperation in experiment
50 g With boron tribromide In dichloromethane at 0 - 27℃; for 4 h; A solution of 5-methoxy-7-azaindole (75 g) and dichloromethane (1500 mL) to was cooled to 0-5°C. Boron tribromide (253 g) was added and the reaction mass was warmed to 27°C and stirred for 4 hours. After cooling to 0-5°C, the reaction mass was quenc hed with methanol (225 mL). The reaction mass was stirred for 1 hour at 27°C.The organic layer was th en concentrated under vacuum at 45°C. Ethyl acetate was added and the reaction mixture was stirred for 2 hours at room temperature before filtering. The obtained solid was washed with ethyl acetate (75 mL) then added to water (450 mL). The pH of the reaction mixture was adjusted to 7-8 using 10percent aqueous sodium bicarbonate solution and then cooled to 0-5°C. The solution was filtered and the solid was washed with deionized water (75 mL). The solid was dried the solid under vacuum oven at 50°C for 4 hou rs. (50 g, Yield: 0.66 w/w).
Reference: [1] Patent: EP1154774, 2005, B1, . Location in patent: Page/Page column 113
[2] Patent: WO2018/29711, 2018, A2, . Location in patent: Page/Page column 32
  • 4
  • [ 754214-56-7 ]
  • [ 98549-88-3 ]
YieldReaction ConditionsOperation in experiment
5.8 g With sodium perborate tetrahydrate; sodium hydroxide In tetrahydrofuran at 20℃; for 2 h; The above 7-azaindole-5-doceteol borate, 220 mL of tetrahydrofuran,220 mL of 2 M sodium hydroxide solution and 17.5 g of sodium perborate tetrahydrate at room temperature for 2 h (TLC monitoring of 7-azaindole-5-doceteol borate) was complete, the organic phase was separated and the aqueous phase was washed with 10 percent Hydrochloric acid to adjust the pH to 3-4, precipitation of white solid, suction filtration, 100mL water, 50 vacuum drying overnight to obtain 5.8g in white, the yield of 78percent. HPLC purity: 99.2percent.
Reference: [1] Patent: CN107033142, 2017, A, . Location in patent: Paragraph 0016; 0030; 0032; 0035; 0038; 0041
  • 5
  • [ 685514-01-6 ]
  • [ 98549-88-3 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2317 - 2319
  • 6
  • [ 111293-48-2 ]
  • [ 98549-88-3 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 743,746
  • 7
  • [ 10592-27-5 ]
  • [ 98549-88-3 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 743,746
  • 8
  • [ 114402-41-4 ]
  • [ 98549-88-3 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 743,746
  • 9
  • [ 99068-42-5 ]
  • [ 98549-88-3 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 743,746
  • 10
  • [ 55052-28-3 ]
  • [ 98549-88-3 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2317 - 2319
  • 11
  • [ 651744-48-8 ]
  • [ 98549-88-3 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2317 - 2319
  • 12
  • [ 685513-98-8 ]
  • [ 98549-88-3 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 11, p. 2317 - 2319
  • 13
  • [ 183208-35-7 ]
  • [ 98549-88-3 ]
Reference: [1] Patent: WO2018/29711, 2018, A2,
[2] Patent: CN107434807, 2017, A,
  • 14
  • [ 98549-88-3 ]
  • [ 106614-28-2 ]
  • [ 1235865-75-4 ]
YieldReaction ConditionsOperation in experiment
76.5% With potassium phosphate In diethylene glycol dimethyl ether at 110℃; for 24 h; To a three-necked flask was added 100 g of 5-hydroxy-7-azaindole (746 mmol), 141 g of methyl 2,4-difluorobenzoate(821 mmol), 237 g of potassium phosphate (1.12 mol) and 500 mL of diethylene glycol dimethyl Ether, 110 ° C for 24 h (HPLC to monitor 5-hydroxy-7-azaindole).The reaction solution was concentrated to dryness, and 2L of ethyl acetate and 2 L of water were added. The organic phase was separated,dried over anhydrous sodium sulfate, and concentrated to dry crude.The crude product was heated to reflux with 1260 mL of ethyl acetate. The mixture was slowly added dropwise to a solution of 1260 mL ofpetroleum ether. After 1 h of dropping, the mixture was stirred for 1 h, slowly cooled to 25 ° C, filtered and dried to give163g of pale white solidRate of 76.5percent.HPLC purity 98percent.
62% With potassium phosphate In diethylene glycol dimethyl ether at 115℃; for 10 h; Inert atmosphere Under a nitrogen atmosphere,1H-pyrrolo[2,3-b]pyridin-5-ol (1.0 g, 7.45 mmol), Methyl 2,4-difluorobenzoate (1.6 g, 9.31 mmol), Potassium phosphate (2.05g, 9.69mmol)Add to 20mL diglyme solution,The reaction solution was stirred at 115 ° C for about 10 h.Plate analysis until the starting material is completely reacted.The reaction solution was cooled to room temperature, then quenched with water and ethyl acetate.Collect organic phase,Purification by column chromatography gave a white solid product (1.3 g).The yield was 62percent.
22.2% With potassium phosphate heptahydrate In diethylene glycol dimethyl ether at 115℃; Inert atmosphere 1H-pyrrolo [2,3-b] pyridin-5-ol(1.20 g, 8.95 mmol, 1.03 eq) and methyl 2,4-difluorobenzoate (1.5 g, 8.71 mmol, 1.0 eq) were added to 20 mL of diethylene glycol dimethyl ether, followed by addition of potassium phosphate heptahydrate (3.5 G,14.0 mmol, 1.6 eq) under nitrogen atmosphere at 115 ° C overnight. TLC point plate analysis, as well as raw materials, most of which produce ortho products. TLC point plate analysis, as well as raw materials, add 0.3g 2,4-difluorobenzoic acid methyl ester and 0.5g potassium phosphate heptahydrate, continue to react overnight. And then TLC point board analysis, the effect is not very good, as well as raw materials. (30 mL × 3), the organic phase was dried with anhydrous sodium sulfate, spin-dried column, PE / EA (v / v) = 3/1 column, white Solid 525mg. Yield 22.2percent.
588 mg With potassium phosphate In 1,4-dioxane at 34 - 90℃; for 47 h; To a mixture of methyl 2,4-difluoro benzoate (1.0 g) in 1,4-dioxane (20 mL), 5-hydroxypyrrolo[2,3-b]pyridine (779 mg) and K3P04 (1.47 g) were added at 34°C and heated to90°C. The reaction mixture is stirred at the same temperature for 23 hours. K3P04 (396mg) was added at 90°C to the reaction mixture and stirred for another 24 hours at thesame temperature. Cooled the reaction mixture to 32°C and filtered on a celite bed.Washed the celite bed with ethyl acetate (20 mL) and evaporated the solvent in the filtrateto obtain crude product. The crude product was purified by column chromatography using60-120 silica gel mesh and 10-50percent ethyl acetate- hexane as eluent to obtain the titlecompound as white solid. Yield: 588 mg; Purity by HPLC: 98.73percent
80 g With potassium phosphate In diethylene glycol dimethyl ether at 110℃; A mixture of formula 8 (R=methyl and X=F, 100 g), formula 7 (152 g), potassium phosphate (190 g),and diglyme were stirred at 1 1 Ο°C for 20-22 hours. Afte r cooling, the reaction mixture was filtered through a Celite bed and the filtrate was washed with diglyme (150 mL). Activated carbon (10 g) was charged and the mixture was stirred for 1 hour. The reaction mass was filtered through a Celite bed and the filtrate was washed with diglyme. Water (3000 mL)was added to the mother liquor and the mixture was stirred at 0- 5°C for 2 hours. The mixture was then filtered and the obtained solid was washed with water (450 mL) then dried at 60°C under vacuum. Toluene was added and the mixture was stirred at 80°C. After cooling to 0-5°C, the reaction mixture stirred for 2 hours, filtered, and the obtained solid was washed with chilled toluene. The solid was suck dried then dried under vacuum (50mm Hg) at 50 (80g, Yield: 0.8 w/w).

Reference: [1] Patent: CN107089981, 2017, A, . Location in patent: Paragraph 0033; 0034; 0035; 0036
[2] Patent: CN108658983, 2018, A, . Location in patent: Paragraph 0110; 0111; 0112
[3] Patent: CN106565706, 2017, A, . Location in patent: Paragraph 0188; 0189; 0190
[4] Patent: WO2017/212431, 2017, A1, . Location in patent: Page/Page column 57; 58
[5] Patent: WO2018/29711, 2018, A2, . Location in patent: Page/Page column 32; 33
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