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[ CAS No. 271-29-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 271-29-4
Chemical Structure| 271-29-4
Chemical Structure| 271-29-4
Structure of 271-29-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 271-29-4 ]

CAS No. :271-29-4 MDL No. :MFCD01686899
Formula : C7H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :XLKDJOPOOHHZAN-UHFFFAOYSA-N
M.W : 118.14 Pubchem ID :9219
Synonyms :

Calculated chemistry of [ 271-29-4 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.09
TPSA : 28.68 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) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.07
Log Po/w (XLOGP3) : 0.98
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.31
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 1.22

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.93
Solubility : 1.39 mg/ml ; 0.0118 mol/l
Class : Very soluble
Log S (Ali) : -1.17
Solubility : 7.98 mg/ml ; 0.0675 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.86
Solubility : 0.163 mg/ml ; 0.00138 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 271-29-4 ]

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 [ 271-29-4 ]

* 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 [ 271-29-4 ]
  • Downstream synthetic route of [ 271-29-4 ]

[ 271-29-4 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 64608-65-7 ]
  • [ 274-45-3 ]
  • [ 271-29-4 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 6353
  • 2
  • [ 64608-65-7 ]
  • [ 86119-84-8 ]
  • [ 10025-87-3 ]
  • [ 274-45-3 ]
  • [ 271-29-4 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 6353
  • 3
  • [ 357263-41-3 ]
  • [ 271-29-4 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogen In ethanol at 20℃; A suspension of 7-chloro-1H-pyrrolo[2,3-c]pyridine (650 mg, 4.2 mmol) and Pd/C (10percent, 50 mg) in EtOH (25 mL) was stirred at RT under H2 atmosphere (balloon pressure).
The reaction mixture was filtered through a celite pad, and the filter cake was washed with EtOAc (10 mL).
The filtrate was concentrated and purified via flash chromatography (DCM/MeOH/NH4OH, 9/1/0.1), affording 1H-Pyrrolo[2,3-c]pyridine as a white solid (380 mg, 75percent yield).
70.95% With sodium tetrahydroborate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 60 h; Inert atmosphere To a solution of anhydrous THF (35.50 mL) was added 43 (0.71 g, 4.42 mmol). The resulting solution was degassed for 2 h using N2. Hereafter, PdCl2(dppf)*CH2Cl2 (180.50 mg, 0.22 mmol), TMEDA (2.25 mL, 15.03 mmol) and NaBH4 (0.57 g, 15.03 mmol) were added in sequence. The reaction was allowed to continue for 60 h at ambient temperature. The reaction was quenched by slowly pouring the solution in brine. After extraction with EtOAc ( .x. 3), the combined organic fractions were filtered over Hyflo Super Cel medium (calcined), concentrated in vacuo and purified using automated flash chromatography (EtOAc/MeOH/NH4OH, 960:37.5:2.5) to give 37 (0.39 g; 70.95percent yield). Note: This procedure was repeated multiple times using batches of 43 (0.25-2.5 g), giving consistent 65-75percent yields at reaction times of 14-60 h 1H NMR (400 MHz, CDCl3) δ 8.75 (s, 1H), 8.04 (d, J = 5.5 Hz, 1H), 7.53-7.46 (m, 1H), 7.43 (t, J = 2.8 Hz, 1H), 6.64 (dd, J = 3.0, 2.1 Hz, 1H).
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 7, p. 2345 - 2347
[2] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9531 - 9540
[3] Patent: US2007/123535, 2007, A1, . Location in patent: Page/Page column 43
[4] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5086 - 5098
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4009 - 4022
[6] Patent: WO2010/51781, 2010, A1, . Location in patent: Page/Page column 50
[7] Patent: US2011/263541, 2011, A1, . Location in patent: Page/Page column 37
  • 4
  • [ 180253-66-1 ]
  • [ 271-29-4 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 6, p. 1357 - 1360
[2] Synthesis, 1996, # 7, p. 877 - 882
  • 5
  • [ 142078-36-2 ]
  • [ 271-29-4 ]
Reference: [1] Patent: WO2010/42337, 2010, A1, . Location in patent: Page/Page column 46
  • 6
  • [ 185139-01-9 ]
  • [ 271-29-4 ]
Reference: [1] Synthesis, 1996, # 7, p. 877 - 882
  • 7
  • [ 7633-56-9 ]
  • [ 271-29-4 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogenchloride In tetrahydrofuran c
1H-Pyrrolo[2,3-c]pyridine
The azaindoline (step b, 1.1 g, 5.0 mmol) was dissolved in tetrahydrofuran (20 ml) and treated with 5.5M hydrochloric acid (5 ml).
The mixture was heated at 50° C. for 4.5 hours cooled to 0° C. and basified with 5M sodium hydroxide (7.0 ml).
The mixture was extracted with ethyl acetate (2*20 ml) and the combined ethyl acetate fractions were washed with saturated brine (20 ml), dried (Na2 SO4), filtered and concentrated in vacuo to afford the title compound as a pale yellow crystalline solid; yield: 0.57 g (97percent).
mp. 132°-134° C.Lit. mp 131°-132°[C.].
Reference: [1] Patent: US5681959, 1997, A,
  • 8
  • [ 5470-18-8 ]
  • [ 271-29-4 ]
Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 7, p. 2345 - 2347
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 5086 - 5098
[3] Patent: US2011/263541, 2011, A1,
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 22, p. 9531 - 9540
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 10, p. 4009 - 4022
  • 9
  • [ 146336-81-4 ]
  • [ 271-29-4 ]
Reference: [1] Heterocycles, 1992, vol. 34, # 12, p. 2379 - 2384
  • 10
  • [ 2530-26-9 ]
  • [ 1826-67-1 ]
  • [ 271-29-4 ]
Reference: [1] Patent: US2003/171395, 2003, A1,
  • 11
  • [ 1003-29-8 ]
  • [ 271-29-4 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 6353
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 6353
  • 12
  • [ 64608-65-7 ]
  • [ 274-45-3 ]
  • [ 271-29-4 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 6353
  • 13
  • [ 56700-70-0 ]
  • [ 271-29-4 ]
Reference: [1] Synthesis, 1996, # 7, p. 877 - 882
  • 14
  • [ 67058-74-6 ]
  • [ 271-29-4 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1956, vol. 599, p. 233,235
  • 15
  • [ 64608-65-7 ]
  • [ 86119-84-8 ]
  • [ 10025-87-3 ]
  • [ 274-45-3 ]
  • [ 271-29-4 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 6353
  • 16
  • [ 271-29-4 ]
  • [ 75-36-5 ]
  • [ 67058-71-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2834 - 2844
[2] Journal of Organic Chemistry, 2002, vol. 67, # 17, p. 6226 - 6227
  • 17
  • [ 271-29-4 ]
  • [ 67058-76-8 ]
Reference: [1] Synlett, 2005, # 15, p. 2400 - 2402
[2] Synlett, 2007, # 2, p. 211 - 214
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2834 - 2844
[4] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2430 - 2433
  • 18
  • [ 271-29-4 ]
  • [ 67058-77-9 ]
YieldReaction ConditionsOperation in experiment
50% at 0 - 20℃; To a solution of 1H-pyrrolo[2,3-c]pyridine (1 g, 8.47 mmol) in H2S04 (5 mL) was added 69percent HNO3 (533 mg, 8.47 mmol) at 0 °C. After stirred at 0 °C for 2 hrs, the reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was then poured into H20 (100 mL) and basified by NaOH powder to pH> 7. Then the mixture was extracted by EA (100 mL x3), dried over anhydrous Na2SO4, and evaporated in vacuum to afford 3-nitro-1H- pyrrolo[2,3-c]pyridine (690 mg, 50percent) as a yellow solid. ‘H NIVIR (400 IVIHz, DMSO-d6): ö = 8.94 (s, 1H), 8.85 (s, 1H), 8.44 (d, J= 5.2 Hz, 1H), 8.02 (dd, J= 5.6, 1.2 Hz, 1H). MS: m/z 164.0 (M+H).
Reference: [1] Patent: WO2018/132372, 2018, A1, . Location in patent: Paragraph 00729
  • 19
  • [ 271-29-4 ]
  • [ 4885-02-3 ]
  • [ 25957-65-7 ]
YieldReaction ConditionsOperation in experiment
0.295 g With aluminum (III) chloride In nitromethane; 1,2-dichloro-ethane at 0℃; for 1 h; Inert atmosphere To a solution of 1 /-/-pyrrolo[2,3-c]pyridine (0.400 g; 3.386 mmol) in a mixture of 1 ,2- dichloroethane (10 mL) and nitromethane (10 mL) cooled at 0 °C under an argon atmosphere were added dichloro(methoxy)methane (1.544 mL; 16.92 mmol) and aluminum trichloride (1.500 g; 1 1.25 mmol) over 1 h. After the addition, the reaction was quenched by addition of water and of a saturated sodium bicarbonate solution. The reaction mixture was extracted with a solution of dichloromethane and ethanol (9/1 , 6x100 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield 0.295 g (60percent) of 1 H-pyrrolo[2,3-c]pyridine-3-carbaldehyde which was used without further purification. ESI/APCI(+): 147 (M+H). ESI/APCI(-): 145 (M-H). 1H NMR (DMSO- ofe) δ 10.01 (1 H, s); 8.88 (1 H, s); 8.50 (1 H, s); 8.33 (1 H, d); 8.00 (1 H, d).
Reference: [1] Patent: WO2013/45516, 2013, A1, . Location in patent: Page/Page column 200
  • 20
  • [ 271-29-4 ]
  • [ 100-97-0 ]
  • [ 25957-65-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5151 - 5164
  • 21
  • [ 271-29-4 ]
  • [ 956003-24-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5129 - 5136
[2] Patent: US2010/292262, 2010, A1, . Location in patent: Page/Page column 11
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 11, p. 2617 - 2621
  • 22
  • [ 271-29-4 ]
  • [ 1174038-65-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 6, p. 2834 - 2844
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