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[ CAS No. 221675-35-0 ] {[proInfo.proName]}

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Chemical Structure| 221675-35-0
Chemical Structure| 221675-35-0
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Product Details of [ 221675-35-0 ]

CAS No. :221675-35-0 MDL No. :MFCD09998715
Formula : C10H10N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CBIVEMGUNRNUEB-UHFFFAOYSA-N
M.W : 190.20 Pubchem ID :21868741
Synonyms :

Calculated chemistry of [ 221675-35-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.2
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 52.18
TPSA : 54.98 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) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.98
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 1.74
Log Po/w (MLOGP) : 1.2
Log Po/w (SILICOS-IT) : 2.17
Consensus Log Po/w : 1.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.48
Solubility : 0.637 mg/ml ; 0.00335 mol/l
Class : Soluble
Log S (Ali) : -2.65
Solubility : 0.429 mg/ml ; 0.00226 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.39
Solubility : 0.0768 mg/ml ; 0.000404 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.87

Safety of [ 221675-35-0 ]

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

Application In Synthesis of [ 221675-35-0 ]

* 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 [ 221675-35-0 ]
  • Downstream synthetic route of [ 221675-35-0 ]

[ 221675-35-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 221675-35-0 ]
  • [ 394223-03-1 ]
YieldReaction ConditionsOperation in experiment
67%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at -20℃; for 2 h;
Stage #2: With water; ammonium chloride In tetrahydrofuran
Step c: lH-pyrrolo[2,3-.pound.]pyridine-2-carbaldehyde[0452] A solution of ethyl lH-pyrrolo[2,3-3/4]pyridine-2-carboxylate (190 mg, 1.0 mmol) in THF (5.0 mL) was added dropwise to a suspension of LiAlH4 (42 mg, 1.1 mmol) in THF (10.0 mL) at -20°C and the reaction mixture was stirred at -20°C for 2 h. The reaction was quenched with saturated NH4C1 solution (10.0 mL). The resulting mixture was filtered and the filtration cake was washed with ethyl acetate. The combined filtrates were washed with brine, dried over anhydrous Na2S04 and concentrated to afford 120 mg of the title compound (67percent yield), which was used as such in the next step.
Reference: [1] Patent: WO2012/178015, 2012, A2, . Location in patent: Page/Page column 113
  • 2
  • [ 287384-79-6 ]
  • [ 221675-35-0 ]
YieldReaction ConditionsOperation in experiment
100% at 20 - 50℃; A mixture of compound 29 (9.7 g, 31.4 mmol, 1 eq) in a solution of HCl (50 mL, 6 N) was stirred at 50 °C for 2 h and r.t. overnight. The reaction mixture was adjusted to pH 13 with solid K2CO3 and was extracted with EtOAc. The organic phase was dried over sodium sulfate, filtered and evaporated under reduced pressure to give 30 (6.0 g, 100percent). 1H NMR (400 MHz, DMSO) 11.12 (br s, 1H), 8.59 (d, J = 4.8 Hz, 1H), 8.05 (dd, J = 8.0, 1.6 Hz, 1H), 7.19 (s, 1H), 7.18-7.15 (m, 1H), 4.46 (q, J = 6.8 Hz, 2H), 1.44 (t, J = 6.8 Hz, 3H).
100% With hydrogenchloride In water at 20 - 50℃; Ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate (135)[00505] A mixture of compound 134 (9.7 g, 31.4 mmol, 1 eq) in a solution of HC1 (50 mL, 6 N) was stuffed at 50 °C for 2 h and r.t. overnight. The reaction mixture was adjusted to pH 13 with solid K2C03 and was extracted with EA. The organic phase was dried over sodium sulfate, filtered and evaporated under reduced pressure to give compound 135 (6.0 g, 100percent). [00506] ‘H NMR (400 MHz, DMSO) ‘Y 11.12 (br s, 1H), 8.59 (d, J= 4.8 Hz, 1H), 8.05 (dd, J= 8.0, 1.6 Hz, 1H), 7.19 (s, 1H), 7.18-7.15 (m, 1H), 4.46 (q, J= 6.8 Hz, 2H), 1.44 (t, J= 6.8 Hz, 3H).
Reference: [1] European Journal of Medicinal Chemistry, 2014, vol. 88, p. 3 - 9
[2] Patent: WO2015/187428, 2015, A1, . Location in patent: Paragraph 00502; 00505; 00506
[3] Patent: US2009/318455, 2009, A1, . Location in patent: Page/Page column 69; 93
  • 3
  • [ 128071-75-0 ]
  • [ 105-56-6 ]
  • [ 221675-35-0 ]
YieldReaction ConditionsOperation in experiment
35% With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 50℃; for 3 h; Step b: ethyl lH-pyrrolo[2,3-.pound.]pyridine-2-carboxylate[0451] A mixture of 2-bromonicotinaldehyde (1.0 g, 5.4 mmol), ethyl 2-cyanoacetate (0.69 g, 6.0 mmol), Cul (115 mg, 0.6 mmol) and Cs2C03 (3.59 g, 11.0 mmol) in DMF (10.0 mL) was stirred at 50°C for 3 h. After the mixture was cooled to room temperature, it was poured into saturated NH4C1 solution (50.0 mL). The resulting mixture was extracted with DCM and the combined organic layers were washed with brine, dried over anhydrous Na2S04 andconcentrated. The residue was purified by flash column chromatography (PE/EA//DCM = 80/10/5 to 60/10/10) to afford 0.35 g of the title compound as a yellow solid (35percent yield).
Reference: [1] Patent: WO2012/178015, 2012, A2, . Location in patent: Page/Page column 113
  • 4
  • [ 138343-75-6 ]
  • [ 95-92-1 ]
  • [ 221675-35-0 ]
Reference: [1] Patent: US2008/125459, 2008, A1, . Location in patent: Page/Page column 10-11
[2] Patent: US2009/298865, 2009, A1, . Location in patent: Page/Page column 7
  • 5
  • [ 64-17-5 ]
  • [ 189089-90-5 ]
  • [ 221675-35-0 ]
YieldReaction ConditionsOperation in experiment
94% for 20 h; Reflux 4.2.24
Ethyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate (18)
Compound 17 (302 mg, 1.00 mmol), EtOH (20 mL) and concentrated sulfuric acid (0.2 mL) were mixed in a round bottom flask and stirred under reflux for 20 h.
The reaction mixture was cooled to room temperature and concentrated under reduced pressure.
The residue was solubilized in EtOAc and washed three times with a saturated sodium hydrogenocarbonate solution, washed with water and a saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure.
The crude product was purified by chromatography on silica gel column, CH2Cl2/EtOAc 8:2, to give 178 mg of the expected product as a white solid in 94percent yield. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 12.49 (br, 1H), 8.41 (dd, J = 1.7, 4.6 Hz, 1H), 8.11 (dd, J = 1.6, 8.0 Hz, 1H), 7.17 (s, 1H), 7.16 (dd, J = 4.6, 8.0 Hz, 1H), 3.34 (q, J = 7.1 Hz, 2H), 1.34 (t, J = 7.1 Hz, 3H).
13C NMR (75 MHz, DMSO-d6) δ (ppm): 161.5, 149.3, 147.2, 131.2, 128.3, 119.5, 117.3, 106.9, 61.1, 14.7.
Reference: [1] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1019 - 1022
  • 6
  • [ 1205747-95-0 ]
  • [ 221675-35-0 ]
Reference: [1] Patent: US2011/112104, 2011, A1, . Location in patent: Page/Page column 5
  • 7
  • [ 2999-46-4 ]
  • [ 128071-75-0 ]
  • [ 221675-35-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 19, p. 4708 - 4713
[2] Chemical Communications, 2009, # 48, p. 7581 - 7583
  • 8
  • [ 64-17-5 ]
  • [ 136818-50-3 ]
  • [ 221675-35-0 ]
YieldReaction ConditionsOperation in experiment
60% for 4 h; Reflux A solution of lH-pyrrolo[2,3-b]pyridine-2-carboxylic acid (20 g, 123 mmol), H2S04 (20 mL) and EtOH is heated to reflux for 4h. The reaction mixture is concentrated in vacuo, taken up in EtOAc and washed with sat. NaHC03 (2X), H20 and brine, dried over MgS04, filtered, and concentrated in vacuo to yield 14 g (60percent) of desired product. 1H-NMR (CDC13, 300 MHz) δ 11.6 (bs, H), 8.6 (d, H), 8.1 (d, H), 7.2 (m,2 H), 4.45 (m, 2H),1.5 (m, 3H). LCMS m/z 191 (M+H).
Reference: [1] Patent: WO2011/78984, 2011, A1, . Location in patent: Page/Page column 23; 24
  • 9
  • [ 108-99-6 ]
  • [ 221675-35-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 22, p. 6888 - 6895,8
  • 10
  • [ 271-63-6 ]
  • [ 221675-35-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1019 - 1022
[2] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
  • 11
  • [ 143141-23-5 ]
  • [ 221675-35-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 3, p. 1019 - 1022
[2] European Journal of Medicinal Chemistry, 2016, vol. 108, p. 701 - 719
  • 12
  • [ 138343-75-6 ]
  • [ 221675-35-0 ]
Reference: [1] Patent: US2011/112104, 2011, A1,
  • 13
  • [ 1603-40-3 ]
  • [ 221675-35-0 ]
Reference: [1] Patent: US2011/112104, 2011, A1,
  • 14
  • [ 109-04-6 ]
  • [ 221675-35-0 ]
Reference: [1] Patent: WO2012/178015, 2012, A2,
  • 15
  • [ 221675-35-0 ]
  • [ 577711-94-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1207 - 1211
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