Home Cart 0 Sign in  
X

[ CAS No. 272-49-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 272-49-1
Chemical Structure| 272-49-1
Chemical Structure| 272-49-1
Structure of 272-49-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 272-49-1 ]

Related Doc. of [ 272-49-1 ]

Alternatived Products of [ 272-49-1 ]

Product Details of [ 272-49-1 ]

CAS No. :272-49-1 MDL No. :MFCD00971977
Formula : C7H6N2 Boiling Point : -
Linear Structure Formula :- InChI Key :XWIYUCRMWCHYJR-UHFFFAOYSA-N
M.W : 118.14 Pubchem ID :9226
Synonyms :

Calculated chemistry of [ 272-49-1 ]

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 : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.12
Log Po/w (XLOGP3) : 1.07
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.58
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 1.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.99
Solubility : 1.22 mg/ml ; 0.0103 mol/l
Class : Very soluble
Log S (Ali) : -1.26
Solubility : 6.44 mg/ml ; 0.0545 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 : 1.29

Safety of [ 272-49-1 ]

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 [ 272-49-1 ]

* 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 [ 272-49-1 ]
  • Downstream synthetic route of [ 272-49-1 ]

[ 272-49-1 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 18699-87-1 ]
  • [ 4637-24-5 ]
  • [ 3430-10-2 ]
  • [ 272-49-1 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 6, p. 1357 - 1360
  • 2
  • [ 272-49-1 ]
  • [ 824-51-1 ]
Reference: [1] Patent: WO2013/10880, 2013, A1,
  • 3
  • [ 272-49-1 ]
  • [ 55052-27-2 ]
Reference: [1] Patent: WO2013/10880, 2013, A1,
  • 4
  • [ 272-49-1 ]
  • [ 23688-47-3 ]
YieldReaction ConditionsOperation in experiment
89% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 0.5 h; (R)-3-Pyrrolidin-2-ylmethyl-1H-pyrrolo[3,2-b]pyridine.(Compound 88)
4.6 g (25.8 mmol) NBS was added to 3.05 g (25.8 mmol) 4-azaindole in 40 ml of DMF (0° C.).).
The mixture was stirred for 30 minutes at 0° C.
MeOH was added and the mixture was filtrated over SCX-2, followed by flash chromatography (ethyl acetate followed by MeOH) afforded 3-bromo-1H-[3,2-b]pyridine (86) as a solid. mp 241° C. (4.52 g, 89percent).
1H-NMR (400 MHz, D6DMSO) δ 11.7 (bs, 1H), 8.39 (dd, J=5 Hz, 2 Hz, 1H), 7.85 (s, 1H), 7.82 (dd, J=8 Hz, 2 Hz, 1H), 7.19 (dd, J=8 Hz, 5 Hz, 1H).
76%
Stage #1: With copper(ll) bromide In acetonitrile at 17 - 20℃; Cooling
Stage #2: With ammonia In methanol; acetonitrile at 10℃;
Example 3 3-Bromo-4-Azaindole[00147] solution of 0.9707g (8.21 mmol) of 4-azaindole in 50 ml. of acetonitrile was placed in a 250 ml. three-neck round-bottom flask equipped with a magnetic stirrer, thermocouple, nitrogen bleed, and cooling ice bath. A total of 5.5187g (24.7 mmol, 3 eq.) of solid CuBr2 was added portion-wise to the flask at 170C in 10 minutes. The resulting green suspension stirred at room temperature until no starting material was observed by TLC (approximately 1-2 hours). The reaction mixture was cooled to 1 O0C and then was slowly quenched by addition of 7Λ/ ammonia in methanol solution (6OmL). The resulting blue solution was concentrated on rotavap at room temperature, and the residue was extracted with ethyl acetate (3 x 80 mL). The organic extract was dried over Na2SO4, filtered, and concentrated on rotavap to give 1.4g of off-white solid. This residue was suspended in 100 mL of hexane, filtered and dried under suction to give 1.225g (76percent yield) of 3-bromo-4-azaindole as white solid.
67% With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 1 h; Inert atmosphere; Schlenk technique To a stirredsolution of 1H-pyrrolo[3,2-b]pyridine(1.0 g, 8.47 mmol) in dry DMF (10 ml) was added N-bromosuccinimide(1.51 g, 8.48 mmol) at 0 °C and the resultant mixture was stirredfor 1 h at the same temperature. The reaction mixture was dilutedwith saturated sodium bicarbonate solution (50 ml) and extracted withethyl acetate (2 x 150 ml). The combined organic layers were washedwith brine (50 ml) and dried (Na2SO4).The residue obtained after evaporation of the solvent was purified bysilica gel column chromatography using3percent methanol in chloroformm toyield 1.12 g (67percent) of product as a white solid. 1HNMR (300 MHz, DMSO-d6)7.19 (dd, J= 5.1, 4.8 Hz, 1H), 7.81 (d, J= 1.5 Hz, 1H), 7.82 (d, J= 3.0 Hz, 1H), 8.37 (d, J= 4.8 Hz, 1H), 11.69 (br s, 1H).
Reference: [1] Patent: US2008/9514, 2008, A1, . Location in patent: Page/Page column 26
[2] Patent: WO2010/33980, 2010, A2, . Location in patent: Page/Page column 28
[3] Synlett, 2007, # 2, p. 211 - 214
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 15, p. 3238 - 3242
[5] Journal of Medicinal Chemistry, 1997, vol. 40, # 15, p. 2430 - 2433
[6] Patent: EP3345906, 2018, A1, . Location in patent: Paragraph 0156
[7] Patent: WO2008/135442, 2008, A1, . Location in patent: Page/Page column 24
  • 5
  • [ 272-49-1 ]
  • [ 357263-48-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 13, p. 5728 - 5737
[2] Patent: US2015/94328, 2015, A1,
[3] Patent: WO2015/49574, 2015, A1,
[4] Patent: WO2017/59080, 2017, A1,
  • 6
  • [ 272-49-1 ]
  • [ 100-97-0 ]
  • [ 276862-85-2 ]
YieldReaction ConditionsOperation in experiment
89% for 4 h; Reflux A mixture of 4-azaindole (0.500 g; 4.223 mmol), hexamethylenetetramine (0.890 g; 6.348 mmol) and acetic acid (3.630 mL; 63.45 mmol) in water (9 mL) was refluxed for 4 h. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Purification by flash chromatography on silica gel using a gradient of methanol (2percent to 4percent) in dichloromethane furnished 0.550 g (89percent) of 1 /-/-pyrrolo[3,2-£>]pyridine-3-carbaldehyde. ESI/APCI(+): 147 (M+H). ESI/APCI(-): 145 (M-H).
56% With acetic acid In water for 4 h; Heating / reflux A mixture of 1H-pyrrolo[3,2-b]pyridine (947 mg, 8.02 mmol), hexamethylenetetramine (1.7 g, 12 mmol) and acetic acid (7.5 mL) in water (14 mL) was refluxed under N2 for 4 hours.
The reaction mixture was cooled to RT, concentrated, and the residue was purified via flash chromatography (DCM/MeOH/NH4OH) affording 1H-Pyrrolo[3,2-b]pyridin-3-carbaldehyde as a white solid (660 mg, 56percent yield).
Reference: [1] Patent: WO2013/45516, 2013, A1, . Location in patent: Page/Page column 198
[2] Patent: US2007/123535, 2007, A1, . Location in patent: Page/Page column 35
[3] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 5924 - 5934
  • 7
  • [ 272-49-1 ]
  • [ 1083181-26-3 ]
YieldReaction ConditionsOperation in experiment
100% With N-iodo-succinimide In tetrahydrofuran at 20℃; To a solution of lH-pyrrolo[3,2-b]pyridine (1.94 g, 16.4 mmol) in THF (10 mL) is added N- iodosuccimide (4.06 g, 18.1 mmol). Preciptation occurs after a few minutes. The reaction is continued to stri at rt overnight. The preciptate is collected by filtration and is washed with a smalll amount of THF and heptane. The resultin white solid is dried in vacuo. The yeild of the reaction is 4.1 g (quantitative). 1H NMR (OMSO-d6, 300 MHz) δ 8.40 (s, 1H), 7.90-7.70 (m, 2H), 7.15 (d, 1H). LC 0.41 min; MS m/z 245 (M+l).
93.5% With N-iodo-succinimide In tetrahydrofuran at 20℃; To a solution of lH-pyrrolo[3,2-b]pyridine (3.0 g, 25.4 mmol, 1.0 eq) in THF (20 mL) was added NIS (6.3 g, 27.9 mmol, 1.1 eq). Precipitation occurred after a few minutes. The stirring was continued at rt overnight. The precipitate was collected by filtration and washed with a small amount of THF. The resulting solid was dried in vacuum to give 3- iodo-lH-pyrrolo[3,2-b]pyridine (5.8 g, 93.5percent).
9.18 g With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1.08333 h; Inert atmosphere To a mixture of 1H-pyrrolo[3,2-b]pyridine (Purchased from Combi Blocks Inc.), (5 g) and DMF (100 mL) stirred under nitrogen at room temperature was added potassium hydroxide (9.02 g) followed by iodine (12.89 g) and the resulting mixture was stirred at room temperature for 1 h 5 min., then poured onto a mixture of Na2S2O5.5H2O (4.25 g), water (635 mL), and 28-30percent ammonium hydroxide (43 mL).
The resultant mixture was cooled in an ice bath for 20 min, and the precipitate thus produced was filtered and washed with ice water then dried under vacuum to give the title compound (9.18 g).
LCMS: m/z 245.39 [M+H]+.
1H NMR (400 MHz, DMSO-d6) ppm 7.17 (dd, J=8.1, 4.5 Hz, 1H) 7.72-7.87 (m, 2H) 8.38 (d, J=4.4 Hz, 1H) 11.74 (br. s., 1H)
9.18 g With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1.08333 h; Inert atmosphere To a mixture of 1H-pyrrolo[3,2-b]pyridine (Purchased from Combi Blocks Inc.), (5 g) and DMF (100 mL) stirred under nitrogen at room temperature was added potassium hydroxide (9.02 g) followed by iodine (12.89 g) and the resulting mixture was stirred at room temperature for 1 h 5 min., then poured onto a mixture of Na2S2O5.5H2O (4.25 g), water (635 mL), and 28-30percent ammonium hydroxide (43 mL).
The resultant mixture was cooled in an ice bath for 20 min, and the precipitate thus produced was filtered and washed with ice water then dried under vacuum to give the title compound (9.18 g).
LCMS: m/z 245.39 [M+H]+.
1H NMR (400 MHz, DMSO-d6) ppm 7.17 (dd, J=8.1, 4.5 Hz, 1H) 7.72-7.87 (m, 2H) 8.38 (d, J=4.4 Hz, 1H) 11.74 (br. s., 1H)

Reference: [1] Patent: WO2011/78984, 2011, A1, . Location in patent: Page/Page column 72
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6935 - 6938
[3] Patent: WO2018/11628, 2018, A1, . Location in patent: Paragraph 00203
[4] Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5129 - 5136
[5] Patent: US2015/94328, 2015, A1, . Location in patent: Paragraph 0349; 0350-0352
[6] Patent: WO2015/49574, 2015, A1, . Location in patent: Page/Page column 38
Same Skeleton Products
Historical Records

Related Parent Nucleus of
[ 272-49-1 ]

Other Aromatic Heterocycles

Chemical Structure| 4943-67-3

[ 4943-67-3 ]

5-Methyl-1H-pyrrolo[3,2-b]pyridine

Similarity: 0.92

Chemical Structure| 887570-96-9

[ 887570-96-9 ]

5-Fluoro-1H-pyrrolo[3,2-b]pyridine

Similarity: 0.82

Chemical Structure| 183586-34-7

[ 183586-34-7 ]

6-Methyl-1H-pyrrolo[3,2-c]pyridine

Similarity: 0.77

Chemical Structure| 1190320-15-0

[ 1190320-15-0 ]

6-Methyl-1H-pyrrolo[3,2-c]pyridin-3-amine

Similarity: 0.75

Chemical Structure| 272-50-4

[ 272-50-4 ]

5H-Pyrrolo[3,2-d]pyrimidine

Similarity: 0.73