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[ CAS No. 122379-63-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 122379-63-9
Chemical Structure| 122379-63-9
Chemical Structure| 122379-63-9
Structure of 122379-63-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 122379-63-9 ]

CAS No. :122379-63-9 MDL No. :MFCD08272230
Formula : C8H8N2O Boiling Point : -
Linear Structure Formula :- InChI Key :DNIKOOPKCLWWPO-UHFFFAOYSA-N
M.W :148.16 Pubchem ID :11240567
Synonyms :

Calculated chemistry of [ 122379-63-9 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 42.59
TPSA : 37.91 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) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : 1.57
Log Po/w (MLOGP) : 0.7
Log Po/w (SILICOS-IT) : 2.02
Consensus Log Po/w : 1.42

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.1
Solubility : 1.16 mg/ml ; 0.00786 mol/l
Class : Soluble
Log S (Ali) : -1.68
Solubility : 3.13 mg/ml ; 0.0211 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.02
Solubility : 0.142 mg/ml ; 0.000959 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 122379-63-9 ]

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

Application In Synthesis of [ 122379-63-9 ]

* 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.

  • Downstream synthetic route of [ 122379-63-9 ]

[ 122379-63-9 ] Synthesis Path-Downstream   1~55

  • 1
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  • 12
  • [ 2913-97-5 ]
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  • [ 397247-65-3 ]
YieldReaction ConditionsOperation in experiment
58% With n-butyllithium; tert.-butyl lithium; In tetrahydrofuran; hexane; Example 2 2-(1-Hydroxy-2-Phthalimidoethyl)-4-Methoxy-7-Azaindole (8b) Following the previous methodology, from <strong>[122379-63-9]4-methoxy-7-azaindole</strong> (3.55 g, 24 mmol) in THF (75 ml) n-BuLi (16.5 ml, 1.6 M in hexane), t-BuLi (16 ml, 1.7 M in hexane) and a solution of phthalimidoacetaldehyde (5 g, 26 mmol) in THF (100 ml) a crude mixture was obtained, which was purified by flash column chromatography. Elution with CH2Cl2/acetone (95/5) gave 4-methoxyazaindole (2.06 g, 58%) and with CH2C12/MeOH(98/2) afforded 8b (3.68 g, 43%) as a white solid. mp 225-226 C. (CH2Cl2/MeOH). IR (KBr) nu3500 (s, NH/OH), 1702 (s, C=O), 1594 (m), 1395 (m). 1H-NMR (DMSO-d6, 300 MHz) delta3.88 (s, 3H, Me), 3.86 (dd, J 13.8 and 6.0, 1H, H2'), 3.95 (dd, J 13.8 and 7.8, 1H, H2'), 5.00 (ddd, J7.8, 6.0 and 5.1, 1H, H1'), 5.73 (d, J5.1, 1H, OH), 6.30 (d, J 1.8, 1H, H3), 6.58 (d, J 5.4, 1H, H5), 7.83 (m, 4H, Phth), 8.02 (d, J 5.4, 1H, H6), 11.65 (br, 1H, NH). 13C-NMR (DMSO-d6, 75 MHz) delta43.6 (t, C2'), 55.3 (q, Me), 64.2 (d, C1'), 94.0 (d, C5), 97.8 (d, C3), 109.5 (s, C3a), 123.0 (d, Phth-P), 131.6 (s, Phth-ipso), 134.3 (d, Phth-alpha), 138.1 (s, C2), 144.2 (d, C6), 150.3 (s, C7a*), 158.5 (s, C4*), 167.7 (s, Phth-CO). MS (EI) m/z 338 (M+1, 4), 337 (M+, 20), 319 (M-H2O, 44), 177 (100).
  • 13
  • [ 122379-63-9 ]
  • Variolin B [ No CAS ]
  • 19
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  • [ 397247-73-3 ]
  • 21
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  • [ 397247-75-5 ]
  • 22
  • [ 122379-63-9 ]
  • 4-Methoxy-9-trimethylsilanyloxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine [ No CAS ]
  • 23
  • [ 122379-63-9 ]
  • [ 397247-76-6 ]
  • 24
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  • [ 397247-71-1 ]
  • 25
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  • [ 397247-88-0 ]
  • 26
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  • 9-acetylamino-5-(2-acetylaminopyrimidin-4-yl)-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidine [ No CAS ]
  • 27
  • [ 122379-63-9 ]
  • 6,7,8,9-tetrahydro-6-hydroxy-4-methoxypyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-9-one hydrochloride [ No CAS ]
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  • [ 397247-89-1 ]
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  • [ 122379-63-9 ]
  • variolin B [ No CAS ]
  • 31
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  • N-[4-(9-Amino-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-6-yl)-pyrimidin-2-yl]-acetamide [ No CAS ]
  • 32
  • [ 122379-63-9 ]
  • N-(6-Iodo-4-methoxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-9-yl)-4-methyl-benzenesulfonamide [ No CAS ]
  • 33
  • [ 122379-63-9 ]
  • N-[6-(2-Amino-pyrimidin-4-yl)-4-hydroxy-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-9-yl]-4-methyl-benzenesulfonamide [ No CAS ]
  • 34
  • [ 122379-63-9 ]
  • N-{4-[4-Methoxy-9-(toluene-4-sulfonylamino)-pyrido[3',2':4,5]pyrrolo[1,2-c]pyrimidin-6-yl]-pyrimidin-2-yl}-acetamide [ No CAS ]
  • 35
  • aqueous NH4OH [ No CAS ]
  • 5,7-dibromo-4-methoxy-7-azaindole [ No CAS ]
  • [ 122379-63-9 ]
YieldReaction ConditionsOperation in experiment
With hydrazine;palladium-carbon; In ethanol; water; A solution of 5,7-Dibromo-4-methoxy-7-azaindole 36 (680 mg, 2.22 mmol), 5% Pd/C (350 mg, 0.17 mmol) and hydrazine (2.5 mL, 80 mmol) in EtOH was heated at reflux for 1 h. The reaction mixture was allowed to cool to rt, filtered through celite and the filtrate concentrated. Aqueous NH4OH (11% in H2O, 45 mL) was added to the residue and the solution was extracted with CH2C2 (3*30 mL). The combined organics were dried (MgSO4), filtered and concentrated to yield 4-methoxy-7-azaindole 37 (290 mg, 1.95 mmol, 88%) as an orange solid.
With hydrazine;palladium-carbon; In ethanol; water; A solution of 5,7-Dibromo-4-methoxy-7-azaindole 36 (680 mg, 2.22 mmol), 5% Pd/C (350 mg, 0.17 mmol) and hydrazine (2.5 mL, 80 mmol) in EtOH was heated at reflux for 1 h. The reaction mixture was allowed to cool to rt, filtered through celite and the filtrate concentrated. Aqueous NH4OH (11% in H2O, 45 mL) was added to the residue and the solution was extracted with CH2Cl2 (3*30 mL). The combined organics were dried (MgSO4), filtered and concentrated to yield 4-methoxy-7-azaindole 37 (290 mg, 1.95 mmol; 88%) as an orange solid.
  • 36
  • 5,7-dibromo-4-methoxy-7-azaindole [ No CAS ]
  • [ 122379-63-9 ]
YieldReaction ConditionsOperation in experiment
Characterization of 36: 1H NMR (500 MHz, CDCl3) 8.73 (br s, 1H), 7.41 (dd, J=3.1, 2.8 Hz, 1H), 6.69 (d, J=3.1, 2.2 Hz, 1H), 4.13 (s, 3H); 13C NMR (125 MHz, CDC3) 146.6, 133.7, 128.8, 127.5, 120.2, 115.6, 101.9, 60.7. MS m/z (M+H)+calcd for C,H7Br2N2O: 304.88; found 304.88. HPLC retention time: 1.31 minutes (column A). Preparation of 4-methoxy-7-azaindole 37:
Characterization of 36: 1H NMR (500 MHz, CDCl3) 8.73 (br s, 1H), 7.41 (dd, J=3.1, 2.8 Hz, 1H), 6.69 (d, J=3.1, 2.2 Hz, 1H), 4.13 (s, 3H); 13C NMR (125 MHz, CDCl3) 146.6, 133.7, 128.8, 127.5, 120.2, 115.6, 101.9, 60.7. MS m/z (M+H)+calcd for C8H7Br2N2O: 304.88; found 304.88. HPLC retention time: 1.31 minutes (column A). Preparation of 4-methoxy-7-azaindole 37:
  • 38
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  • [ 98-09-9 ]
  • [ 916574-87-3 ]
  • 43
  • [ 122379-63-9 ]
  • C18H24N2O3Si [ No CAS ]
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  • C15H16N2O3 [ No CAS ]
  • 46
  • [ 67-56-1 ]
  • [ 79099-07-3 ]
  • [ 122379-63-9 ]
  • tert-butyl 4-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% To MeOH (1 .5 L) was added Na (57 g, 2.48 mol) in portions over 2 h, and the mixture stirred to afford a clear solution. 4-methoxy-1 /-/-pyrrolo[2,3-b]pyridine (1-120) (64.4 g, 410 mmol) and tert-butyl 4-oxopiperidine-1 -carboxylate (165.0 g, 826 mmol) was added to the NaOMe solution (1 .5L) at 25 C. The reaction mixture was stirred at 80 C for 3 days. LCMS showed about 30% of starting material was remained. The reaction mixture was concentrated to remove MeOH. The residue was diluted into water (1 .5 L) and extracted with EtOAc/THF (2 x 1 .5 L/150 ml_). The extracts were washed with brine (2 x 2 L ). The extract was dried over Na2S04, and concentrated to give a residue (300 g), which was purified by silica gel chromatography (petroleum ether: EtOAc: THF = 3:1 :0.15 to 1 :1 : 0.15) to give te/ -butyl 4-(4-methoxy-1 H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1 (2H)-carboxylate (1-121) (49 g, 35%) as a yellow solid.
  • 47
  • [ 67-56-1 ]
  • [ 55052-28-3 ]
  • [ 122379-63-9 ]
YieldReaction ConditionsOperation in experiment
45% With sodium; at 140℃; for 44h;Autoclave; To MeOH (600 mL) was added Na (22.6 g, 983 mmol.) in portions over 1 hr, and the mixture stirred to afford a clear solution. Then 4-chloro-1 /-/-pyrrolo[2,3-b]pyridine (1-119) (50 g, 327.69 mmol) was added. The reaction mixture was stirred at 140 C for 44 hr in a 1 L autoclave. Some yellow solids formed in the reaction mixture, and LCMS showed about 30% of starting material remained. The reaction mixture was concentrated under vacuum to remove MeOH. The residue was diluted into water (200 mL) and extracted with EtOAc/THF ( 2 x 300 mL/50 mL). The extracts were washed with saturated NH4CI (150 mL) and brine (150 mL). The extract was dried and concentrated to give a crude product, which was purified by silica gel chromatography (petroleum ether: EtOAc: THF = 3:1 :0.2 to 1 :1 : 0.2) and re-crystallized from petroleum ether/CH2CI2/EtOH (600 mL/100 mL/10 mL) to give 4-methoxy-1 H-pyrrolo[2,3-b]pyridine (1-120) (22 g, 45%) as a white solid.
  • 48
  • [ 122379-63-9 ]
  • N-(2-methoxyethyl)-2-[(2R)-1-methoxypropan-2-yl]oxy}-6-[4-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidin-1-yl]pyrimidine-4-carboxamide [ No CAS ]
  • 49
  • [ 122379-63-9 ]
  • tert-butyl 4-(4-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate [ No CAS ]
  • 50
  • [ 122379-63-9 ]
  • 4-methoxy-3-(piperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 51
  • [ 122379-63-9 ]
  • 3-[1-(6-chloro-2-[(2R)-1-methoxypropan-2-yl]oxy}pyrimidin-4-yl)piperidin-4-yl]-4-methoxy-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 52
  • [ 122379-63-9 ]
  • 2,3,3,3-tetrafluoro-1-(4-methoxy-2,3-dihydro-1H-pyrrolo-[2,3-b]pyridin-1-yl)propan-1-one [ No CAS ]
  • 53
  • [ 122379-63-9 ]
  • 4-methoxy-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 54
  • [ 591-50-4 ]
  • [ 122379-63-9 ]
  • 4-methoxy-1-phenyl-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
  • 55
  • [ 591-50-4 ]
  • [ 122379-63-9 ]
  • 1-phenyl-4-(piperidin-1-yl)-1H-pyrrolo[2,3-b]pyridine [ No CAS ]
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