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[ CAS No. 153936-26-6 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 153936-26-6
Chemical Structure| 153936-26-6
Chemical Structure| 153936-26-6
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Product Details of [ 153936-26-6 ]

CAS No. :153936-26-6 MDL No. :MFCD04116209
Formula : C7H10N2 Boiling Point : -
Linear Structure Formula :- InChI Key :QNLAYSBIWHHNIT-UHFFFAOYSA-N
M.W : 122.17 Pubchem ID :1514370
Synonyms :

Calculated chemistry of [ 153936-26-6 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.88
TPSA : 38.91 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) : -10.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.46
Log Po/w (XLOGP3) : -4.86
Log Po/w (WLOGP) : 0.7
Log Po/w (MLOGP) : 0.22
Log Po/w (SILICOS-IT) : 1.41
Consensus Log Po/w : -0.22

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 2.04
Solubility : 13300.0 mg/ml ; 109.0 mol/l
Class : Highly soluble
Log S (Ali) : 4.67
Solubility : 5780000.0 mg/ml ; 47300.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -2.41
Solubility : 0.474 mg/ml ; 0.00388 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.21

Safety of [ 153936-26-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501 UN#:2735
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 153936-26-6 ]

* 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 [ 153936-26-6 ]

[ 153936-26-6 ] Synthesis Path-Downstream   1~93

  • 1
  • [ 64-18-6 ]
  • [ 153936-26-6 ]
  • N-<(3-methyl-2-pyridyl)methyl>formamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% at 0 - 100℃; At 0 C, 3-methyl-2-aminomethylpyridine (5 g, 41 mmol) was added portionwise to formic acid (50 mL). After graduation, The reaction mixture was heated to 100 C overnight. After the reaction is completed, The reaction mixture was cooled to room temperature, The organic solvent was removed by steam distillation under reduced pressure. To the resulting crude product was added a saturated aqueous solution of sodium hydrogencarbonate, Adjust the pH 7 ~ 8, The aqueous phase was extracted with dichloromethane / isopropanol (85:15) (50 mL x 3) The combined organic phases were washed with saturated brine (50 mL) Dried over anhydrous sodium sulfate and evaporated to give N-((3-methylpyridin-2-yl)methyl)formamide (5.4 g, yield 88%).
  • 2
  • [ 153936-26-6 ]
  • 8-methylimidazo<1,5-a>pyridine [ No CAS ]
  • 3
  • trifluoromethanesulfonic acid 6-amino-3-cyano-2-furan-2-yl-pyridin-4-yl ester [ No CAS ]
  • [ 153936-26-6 ]
  • 6-amino-2-furan-2-yl-4-[(pyridin-2-yl-methyl)-amino]-nicotinonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
In 1,2-dimethoxyethane; 6-Amino-2-furan-2-yl-4-[(pyridin-2-yl-methyl)-amino]-nicotinonitrile From trifluoromethanesulfonic acid 6-amino-3-cyano-2-furan-2-yl-pyridin-4-yl ester and <strong>[153936-26-6]C-(3-methyl-pyridin-2-yl)-methylamine</strong> in DME. ES-MS m/e (%): 306 (M+H+, 100).
  • 4
  • [ 917878-65-0 ]
  • [ 153936-26-6 ]
  • 3-chloro-7-[(3-methylpyridin-2-yl)methyl]amino}-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate;copper(l) iodide; rac-Pro-OH; In dimethyl sulfoxide; at 70℃; Example 20; 3-chloro-7-[(3-methylpyridin-2-yl)methyl]amino}-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (Compound 56); 7-bromo-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (0.100 g, 0.312 mmol), <strong>[153936-26-6]2-aminomethyl-3-methylpyridine</strong> (0.038 g, 0.312 mmol), copper iodide (0.006 g, 0.031 mmol), potassium carbonate (0.086 g, 0.621 mmol), and dl-proline (0.007 g, 0.062 mmol) were combined in a flask. Dimethyl sulfoxide (2.0 mL) was added and argon was bubbled through the solution for several minutes. The solution was stirred and heated at 70 C. overnight. Once complete the solution was cooled to ambient temperature, diluted with ethyl acetate and washed with water. The organic layer was dried over magnesium sulftate, filtered, concentrated in vacuo and purified by column chromatography (0-40% ethyl acetate/hexane gradient) to afford the title compound.
  • 5
  • [ 1651-29-2 ]
  • [ 153936-26-6 ]
  • [ 1070791-29-5 ]
YieldReaction ConditionsOperation in experiment
51% With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 20 - 100℃; for 13h; 2-Fluoro-N-((3-methylpyridin-2-yl)methyl)-9H-purin-6-amineTo a stirred solution of 6-chloro-2-fluoropurine (0.4g, 2.3 mmol) in n-BuOH (50 ml) under an argon atmosphere at O0C, was added DIEA (2.5 ml, 14.7 mmol) followed by <strong>[153936-26-6](3-methylpyridin-2-yl)methanamine</strong> (0.36g, 2.95 mmol). The reaction mixture was stirred at this temperature for 1 h and then allowed to return to room temperature and stirred for 4h, it was still seen incomplete, hence heated the reaction to 1000C and left at that temperature for 8h. The solvent was evaporated in vacuo and the residue was <n="71"/>purified by gradient column chromatography on silica gel, eluted with CHCl3: MeOH(100:0 → 90:10), to afford the product as a white solid; Yield: 0.3 g (51%). δH (CDCl3, 500 MHz) 2.35 (3 H, s, CH3), 4.71 (3 H, m, NH and NHCH2), 7.24 (1 H, s,br, ArH), 7.63 (1 H, s, br, ArH), 8.28 (1 H, s, br, ArH), 8.38 (1 H, s, br, ArH); δc (CDCl3, 500 MHz) 161.03 (C), 158.49 (C), 154.77 (C), 152.16 (C), 144.86(CH), 137.53 (CH), 137.14 (CH), 130.67 (C), 121.58 (CH), 118.73 (C), 42.87 (CH2), 18.16 (CH3); m/z 259.3 (M + H)
  • 6
  • [ 506-68-3 ]
  • [ 153936-26-6 ]
  • [ 76-05-1 ]
  • [ 1005514-80-6 ]
YieldReaction ConditionsOperation in experiment
5a) 8-Methylimidazo[1,5-a]pyridin-3-ylamine as the trifluoroacetic acid salt 2-Aminomethyl-3-methylpyridine (500 mg) was dissolved in abs. toluene (15 ml) and cyanogen bromide (455 mg, dissolved in 5 ml toluene) was added dropwise with stirring. After one hour, the precipitate was filtered off with suction and the mother liquor was discarded. The precipitate and the sticky flask residue were purified by means of preparative HPLC. The product-containing fractions were combined, freed from the acetonitrile and freeze-dried. 191 mg of the desired compound were isolated as the trifluoroacetic acid salt. LCMS-Rt: 0.68 min [M+H+]: 148.1
  • 7
  • [ 1006044-30-9 ]
  • [ 153936-26-6 ]
  • [ 1191888-23-9 ]
YieldReaction ConditionsOperation in experiment
38% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; To a solution of crude 1-(2-(tert-butoxycarbonylamino)acetyl)-4-(hydroxymethyl)piperidine-4-carboxylic acid (200 mg, ~0.632 mmol) in DMF (2 mL) were added HBTU (240 mg, 0.632 mmol), <strong>[153936-26-6]2-aminomethyl-3-methylpyridine</strong> (77 mg, 0.632 mmol) and DIEA (110 μL, 0.632 mmol). The reaction mixture was stirred overnight at rt and purified on RP-HPLC using a mixture of acetonitrile and H2O to give tert-butyl 2-(4-(hydroxymethyl)-4-((3-methylpyridin-2-yl)methylcarbamoyl)piperidin-1-yl)-2-oxoethylcarbamate (100 mg, 38%). LRMS (M+H+) m/z 421.1.
  • 8
  • [ 863548-28-1 ]
  • [ 153936-26-6 ]
  • [ 863546-40-1 ]
  • 9
  • [ 863548-29-2 ]
  • [ 153936-26-6 ]
  • [ 1192345-37-1 ]
  • 10
  • [ 1192345-21-3 ]
  • [ 153936-26-6 ]
  • [ 1192345-29-1 ]
  • 11
  • C11H11N3O3 [ No CAS ]
  • [ 153936-26-6 ]
  • [ 1192345-74-6 ]
  • 12
  • C12H13N3O3 [ No CAS ]
  • [ 153936-26-6 ]
  • [ 1192345-76-8 ]
  • 13
  • [ 863548-30-5 ]
  • [ 153936-26-6 ]
  • [ 863547-37-9 ]
  • 14
  • [ 863548-71-4 ]
  • [ 153936-26-6 ]
  • [ 863548-24-7 ]
  • 15
  • [ 1192345-41-7 ]
  • [ 153936-26-6 ]
  • [ 1192345-52-0 ]
  • 16
  • [ 1192345-43-9 ]
  • [ 153936-26-6 ]
  • [ 1192345-54-2 ]
  • 17
  • [ 1192345-44-0 ]
  • [ 153936-26-6 ]
  • [ 1192345-56-4 ]
  • 18
  • [ 1192345-46-2 ]
  • [ 153936-26-6 ]
  • [ 1192345-58-6 ]
  • 19
  • [ 863548-72-5 ]
  • [ 153936-26-6 ]
  • [ 863548-17-8 ]
  • 20
  • [ 863548-73-6 ]
  • [ 153936-26-6 ]
  • [ 863548-18-9 ]
  • 21
  • [ 863548-74-7 ]
  • [ 153936-26-6 ]
  • [ 863548-19-0 ]
  • 22
  • [ 1018647-71-6 ]
  • [ 153936-26-6 ]
  • [ 1192345-60-0 ]
  • 23
  • [ 863548-75-8 ]
  • [ 153936-26-6 ]
  • [ 863548-23-6 ]
  • 24
  • [ 1018586-06-5 ]
  • [ 153936-26-6 ]
  • [ 1192345-62-2 ]
  • 25
  • [ 1192345-48-4 ]
  • [ 153936-26-6 ]
  • [ 1192345-64-4 ]
  • 26
  • [ 1192345-49-5 ]
  • [ 153936-26-6 ]
  • [ 1192345-66-6 ]
  • 27
  • [ 1192345-50-8 ]
  • [ 153936-26-6 ]
  • [ 1192345-68-8 ]
  • 28
  • [ 863548-76-9 ]
  • [ 153936-26-6 ]
  • [ 863548-20-3 ]
  • 29
  • [ 500349-52-0 ]
  • [ 153936-26-6 ]
  • [ 1192345-70-2 ]
  • 30
  • [ 5398-44-7 ]
  • [ 153936-26-6 ]
  • [ 1192345-32-6 ]
  • 31
  • [ 32710-86-4 ]
  • [ 153936-26-6 ]
  • [ 1232975-30-2 ]
  • 32
  • [ 20970-75-6 ]
  • [ 153936-26-6 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogen; In ethanol; at 20℃; for 4h; <strong>[20970-75-6]3-methyl-2-cyanopyridine</strong> (10 g, 84.6 mmol) was dissolved in ethanol (200 mL) at room temperature, Raney nickel (4 g) was added to the reaction substrate, And then stirred at room temperature under hydrogen in a hydrogen atmosphere overnight. To be completed, Filter solids, The organic solvent was removed by distillation under reduced pressure to give 3-methyl-2-aminomethylpyridine (9.7 g, yield 94%).
  • 33
  • [ 24424-99-5 ]
  • [ 153936-26-6 ]
  • [ 1396734-40-9 ]
  • 34
  • [ 153936-26-6 ]
  • C27H27N3O3S [ No CAS ]
  • 35
  • [ 153936-26-6 ]
  • C28H29N3O3S [ No CAS ]
  • 36
  • [ 153936-26-6 ]
  • C27H31N3O3S [ No CAS ]
  • 37
  • [ 153936-26-6 ]
  • rac-N-(((2S,3R)-3-methyl-1-(2-methyl-4-phenylthiazole-5-carbonyl)piperidin-2-yl)methyl)quinoline-8-carboxamide [ No CAS ]
  • 38
  • [ 153936-26-6 ]
  • rac-N-(((2S,3R)-3-methyl-1-(2-methyl-5-phenylthiazole-4-carbonyl)piperidin-2-yl)methyl)ciuinoline-8-carboxamide [ No CAS ]
  • 39
  • [ 153936-26-6 ]
  • C28H28N4O2S [ No CAS ]
  • 40
  • [ 153936-26-6 ]
  • rac-((2S,3R)-2-((benzo[d]oxazol-2-ylamino)methyl)-3-methylpiperidin-1-yl)(2-methyl-5-phenylthiazol-4-yl)methanone [ No CAS ]
  • 41
  • [ 153936-26-6 ]
  • rac-tert-butyl(((2S,3R)-3-methylpiperidin-2-yl)methyl)carbamate [ No CAS ]
  • 42
  • [ 153936-26-6 ]
  • C23H30FN3O3S [ No CAS ]
  • 43
  • [ 153936-26-6 ]
  • C23H31N3O3S [ No CAS ]
  • 44
  • [ 153936-26-6 ]
  • C23H31N3O3S [ No CAS ]
  • 45
  • [ 153936-26-6 ]
  • rac-((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(5-(4-fluorophenyl)-2-methylthiazol-4-yl)methanone [ No CAS ]
  • 46
  • [ 153936-26-6 ]
  • rac-((2S,3R)-2-(aminomethyl)-3-methylpiperidin-1-yl)(2-methyl-5-phenylthiazol-4-yl)methanone [ No CAS ]
  • 47
  • [ 153936-26-6 ]
  • C18H23N3OS [ No CAS ]
  • 48
  • [ 153936-26-6 ]
  • [ 1396756-47-0 ]
  • 49
  • [ 153936-26-6 ]
  • C12H24N2O2 [ No CAS ]
  • 50
  • [ 153936-26-6 ]
  • C23H31N3O3S [ No CAS ]
  • 51
  • [ 153936-26-6 ]
  • C18H23N3OS [ No CAS ]
  • 52
  • [ 153936-26-6 ]
  • C28H27FN4O2S [ No CAS ]
  • 53
  • [ 98-88-4 ]
  • [ 153936-26-6 ]
  • N-[(3-methylpyridin-2-yl)methyl]benzamide [ No CAS ]
  • 54
  • [ 98-88-4 ]
  • [ 153936-26-6 ]
  • 7-Methyl-3-phenyl-imidazo[1,5-a]pyridine [ No CAS ]
  • 55
  • [ 153936-26-6 ]
  • [ 172843-97-9 ]
  • C18H27N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In dichloromethane; for 72h; General procedure: C-(4-Trifluoromethyl-pyridin-2-yl)-methylamine dihydrochloride (0.5 g, 2.01 mmol), 2- tert-butoxycarbonylamino-2-methylpropionic acid (0.45 g, 2.21 mmol), TBTU (0.71 g, 2.21 mmol) and triethylamine (1.15 mL, 8.23 mmol) are combined in dichioromethane (10 mL) and the mixture stirred for 1 hour. The mixture is washed with 0.2M aqueous NaOH, dried over sodium sulphate and the solvent removed under vacuum. The residue is purified by flash chromatography (eluent 0-100% ethyl acetate in cyclohexane) to give the title compound (703 mg, 97%).U PLC-MS (Method 2): R = 1 .00 mmMS (ESI pos): mlz = 362 (M+H)
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In dichloromethane; for 72h; Example 20d 10634] C-(4-Trifluoromethyl-pyridin-2-yl)-methylamine dihydrochioride (0.5 g, 2.01 mmol), 2-tert-butoxycarbony- lamino-2-methylpropionic acid (0.45 g, 2.21 mmol), TI3TU (0.71 g, 2.21 mmol) and triethylamine (1.15 mE, 8.23 mmol) are combined in dichloromethane (10 mE) and the mixture stirred for 1 hour. The mixture is washed with 0.2M aqueous NaOH, dried over sodium sulphate and the solvent removed under vacuum. The residue is purified by flash chromatography (eluent 0-100% ethyl acetate in cyclohexane) to give the title compound (703 mg, 97%).C-(3-Methyl-pyridin-2-yl)-methylamine(470 mg)4-N-Boc-amino-4-carboxytetrahydropyran(945 mg)3 dayreaction
  • 56
  • 4-(2,6-dimethoxybenzamido)-1H-pyrazole-3-carboxylic acid [ No CAS ]
  • [ 153936-26-6 ]
  • 4-(2,6-dimethoxybenzamido)-N-((3-methylpyridin-2-yl)methyl)-1H-pyrazole-3-carboxamide [ No CAS ]
  • 57
  • [ 55589-47-4 ]
  • [ 153936-26-6 ]
  • (E)-1-(3-methylpyridin-2-yl)-N-((3-methylpyridin-2-yl)methylene)methanamine [ No CAS ]
  • 58
  • [ 55589-47-4 ]
  • [ 153936-26-6 ]
  • 2,3,5,6-tetrakis(3-methylpyridin-2-yl)piperazine [ No CAS ]
  • 59
  • 5-(5-((1H-indazol-5-yl)carbamoyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidin-4-yl)-2-fluorobenzoic acid [ No CAS ]
  • [ 153936-26-6 ]
  • 4-(4-fluoro-3-(((3-methylpyridin-2-yl)methyl)carbamoyl)phenyl)-N-(1H-indazol-5-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide [ No CAS ]
  • 60
  • [ 153936-26-6 ]
  • 2-(8-methylimidazolo[1,5-a]pyridin-3-yl)propan-2-amine hydrochloride [ No CAS ]
  • 61
  • [ 153936-26-6 ]
  • C26H32N4O4 [ No CAS ]
  • 62
  • [ 153936-26-6 ]
  • C21H24N4O2 [ No CAS ]
  • 63
  • [ 30992-29-1 ]
  • [ 153936-26-6 ]
  • (2-methyl-1-(((3-methylpyridin-2-yl)methyl)amino)-1-oxopropan-2-yl)carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; at 20℃; 3-methyl-2-(aminomethyl)pyhdine (13.5 g, 1 10 mmol), is suspended in dry THF and 2-tert-butoxycarbonylamino-2-methylpropionic acid (22.4 g, 1 10 mmol) is added followed by TEA (46.1 mL, 331 mmol) and TBTU (35.4 g, 1 10 mmol). The mixture is stirred overnight at room temperature then the solvent is evaporated, the residue is diluted with dichloromethane and washed with 1 N NaOH solution and brine. The organic layer is dried, filtered and evaporated under reduced pressure to give a residue that is purified by flash chromatography (eluent 50-100% EtOAc/cyclohexane) to furnish the title compound (28.5 g, 84%). UPLC-MS (Method 2): Rt = 0.98 min MS (ESI+): m/z = 308 (M+H)+
84% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In tetrahydrofuran; at 20℃; 3-methyl-2-(aminomethyl)pyhdine (13.5 g, 1 10 mmol), is suspended in dry THF and 2-tert-butoxycarbonylamino-2-methylpropionic acid (22.4 g, 1 10 mmol) is added followed by TEA (46.1 mL, 331 mmol) and TBTU (35.4 g, 1 10 mmol). The mixture is stirred overnight at room temperature then the solvent is evaporated, the residue is diluted with dichloromethane and washed with 1 N NaOH solution and brine. The organic layer is dried, filtered and evaporated under reduced pressure to give a residue that is purified by flash chromatography (eluent 50-100% EtOAc/cyclohexane) to furnish the title compound (28.5 g, 84%). UPLC-MS (Method 2): Rt = 0.98 min MS (ESI+): m/z = 308 (M+H)+
  • 64
  • [ 30992-29-1 ]
  • [ 153936-26-6 ]
  • (2-(8-methylimidazolo[1,5-a]pyridin-3-yl)prop-2-yl)carbamic acid tert-butyl ester [ No CAS ]
  • 65
  • [ 153936-26-6 ]
  • C21H30N4O4 [ No CAS ]
  • 66
  • [ 153936-26-6 ]
  • C22H32N4O4 [ No CAS ]
  • 67
  • [ 153936-26-6 ]
  • C22H32N4O4 [ No CAS ]
  • C22H32N4O4 [ No CAS ]
  • 68
  • [ 153936-26-6 ]
  • C22H32N4O4 [ No CAS ]
  • 69
  • [ 153936-26-6 ]
  • C22H32N4O4 [ No CAS ]
  • 70
  • [ 153936-26-6 ]
  • C16H22N4O2 [ No CAS ]
  • 71
  • [ 153936-26-6 ]
  • [ 5977-87-7 ]
  • 8-methyl-3-(p-tolyl)imidazo[1,5-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% General procedure: To a solution of dithioester (1.0 eq, 1.0 mmol) inTHF (2 mL) was added amine or hydrazine (1.1 eq, 1.1 mmol) at room temperature, the resulting mixture was stirred for 45 min. monitored the dithioester could no longer be detected. To the above mixture was added I2 (2.0 equiv. The mixture was stirred at room temperature for 1.5 h and progress was monitored by TLC. The reaction mixture was diluted with EtOAc neutralized with saturated sodium bicarbonate solution, separated organic layer; the aqueous layer was extracted with EtOAc (25 mL X 3). The combined organic layers were washed with water, dried over anhydrous Na2SO4. The solvent was removed under reduced pressure; the residue was purified by silicagel chromatography.
  • 72
  • [ 5969-47-1 ]
  • [ 153936-26-6 ]
  • 3-(4-fluorophenyl)-8-methylimidazo[1,5-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% General procedure: To a solution of dithioester (1.0 eq, 1.0 mmol) inTHF (2 mL) was added amine or hydrazine (1.1 eq, 1.1 mmol) at room temperature, the resulting mixture was stirred for 45 min. monitored the dithioester could no longer be detected. To the above mixture was added I2 (2.0 equiv. The mixture was stirred at room temperature for 1.5 h and progress was monitored by TLC. The reaction mixture was diluted with EtOAc neutralized with saturated sodium bicarbonate solution, separated organic layer; the aqueous layer was extracted with EtOAc (25 mL X 3). The combined organic layers were washed with water, dried over anhydrous Na2SO4. The solvent was removed under reduced pressure; the residue was purified by silicagel chromatography.
  • 73
  • [ 5874-02-2 ]
  • [ 153936-26-6 ]
  • C11H14N2 [ No CAS ]
  • 74
  • 3-amino-5-(4-(methoxymethyl)oxazol-2-yl)-6-methylpyrazine-2-carboxylic acid [ No CAS ]
  • [ 153936-26-6 ]
  • 3-amino-5-(4-(methoxymethyl)oxazol-2-yl)-6-methyl-N-((3-methylpyridin-2-yl)methyl)pyrazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; Step D: 3-Amino-5-(4-(methoxymethyl)oxazol-2-yl)-6-m ethyl -N-((3-methylpyridin-2- yl)methyl)pyrazine-2-carboxamide (Ex-374)[0162] Example compound Ex-374 was prepared from intermediate I-ES-12-A and 2- methylamino-3 -methyl -piperi dine using the proceedures of Schemes ES-1 through ES-5.Ex-374 was characterized by LC/MS and proton NMR. LC/MS = 369[M+1]. 1H MR (MeOD- d4, 400 MHz) d δ: 8.45-8.30 (d, 1H), 8.26-8.23(d, 1H), 8.00(s, 1H), 7.74-7.70 (m, 1H), 4.77 (s, 2H), 4.39 (s, 2H), 3.22-3.20 (m, 5H), 2.72 (s, 3H), 2.50 (s, 3H).
  • 75
  • 3-amino-6-methyl-5-(oxazol-2-yl)pyrazine-2-carboxylic acid [ No CAS ]
  • [ 153936-26-6 ]
  • [ 76-05-1 ]
  • 3-amino-6-methyl-N-((3-methylpyridin-2-yl)methyl)-5-(oxazol-2-yl)pyrazine-2-carboxamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
[0118] Accordingly, to a mixture of <strong>[153936-26-6](3-methylpyridin-2-yl)methanamine</strong> (17 mg, 0.14 mmol) and 3-amino-6-methyl-5-(oxazol-2-yl)pyrazine-2-carboxylic acid (30 mg, 0.14 mmol), DMF (0.55 mL) was added, followed by Hunig's Base (24 μ, 0.14 mmol) and HATU (52 mg, 0.14 mmol) at room temperature. The mixture was allowed to stir at room temperature for overnight, and then directly chromatographed on the prep Gilson HPLC, eluting with gradientacetonitrile/water (containing 0.05% TFA) to afford the TFA salt of 3-amino-6-methyl-N-((3- methylpyridin-2-yl)methyl)-5-(oxazol-2-yl)pyrazine-2-carboxamide as a solid (Ex-3). Ex-3 was characterized by LC/MS. LC/MS = 325 [M+l].
  • 76
  • 3-amino-6-methyl-5-(4-methyl-1H-pyrazol-1-yl)pyrazine-2-carboxylic acid [ No CAS ]
  • [ 153936-26-6 ]
  • 3-amino-6-methyl-5-(4-methyl-1H-pyrazol-1-yl)-N-((3-methylpyridin-2-yl)methyl)pyrazine-2-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 3h; [0125] Hunig's base (0.20 ml, 1.16 mmol) was added to a stirred mixture of 3-amino-6-methyl- 5-(4-methyl-lH-pyrazol-l-yl)pyrazine-2-carboxylic acid (0.090 g, 0.39 mmol), 3-methyl-2- aminomethyl-pyridine (0.052 g, 0.42 mmol) and HATU (0.161 g, 0.42 mmol) in DMF (2 ml) and the mixture was stirred at RT for 3h. The solution was purified by HPLC Gilson with acetonitrile/water with 0.01% TFA as eluants to give the title compound as a solid. LC/MS = 338 [M+l].
  • 77
  • [ 2168-78-7 ]
  • [ 153936-26-6 ]
  • 7-Methyl-3-phenyl-imidazo[1,5-a]pyridine [ No CAS ]
  • 78
  • [ 5874-09-9 ]
  • [ 153936-26-6 ]
  • 3-(4-methoxyphenyl)-8-methylimidazo[1,5-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% General procedure: To a solution of dithioester (1.0 eq, 1.0 mmol) inTHF (2 mL) was added amine or hydrazine (1.1 eq, 1.1 mmol) at room temperature, the resulting mixture was stirred for 45 min. monitored the dithioester could no longer be detected. To the above mixture was added I2 (2.0 equiv. The mixture was stirred at room temperature for 1.5 h and progress was monitored by TLC. The reaction mixture was diluted with EtOAc neutralized with saturated sodium bicarbonate solution, separated organic layer; the aqueous layer was extracted with EtOAc (25 mL X 3). The combined organic layers were washed with water, dried over anhydrous Na2SO4. The solvent was removed under reduced pressure; the residue was purified by silicagel chromatography.
  • 79
  • [ 2168-83-4 ]
  • [ 153936-26-6 ]
  • 8-methyl-3-(thiophen-2-yl)imidazo[1,5-a]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% General procedure: To a solution of dithioester (1.0 eq, 1.0 mmol) inTHF (2 mL) was added amine or hydrazine (1.1 eq, 1.1 mmol) at room temperature, the resulting mixture was stirred for 45 min. monitored the dithioester could no longer be detected. To the above mixture was added I2 (2.0 equiv. The mixture was stirred at room temperature for 1.5 h and progress was monitored by TLC. The reaction mixture was diluted with EtOAc neutralized with saturated sodium bicarbonate solution, separated organic layer; the aqueous layer was extracted with EtOAc (25 mL X 3). The combined organic layers were washed with water, dried over anhydrous Na2SO4. The solvent was removed under reduced pressure; the residue was purified by silicagel chromatography.
  • 80
  • [ 1000071-27-1 ]
  • [ 153936-26-6 ]
  • 5-(3-methylpyridin-2-yl)phenanthridin-6(5H)-one [ No CAS ]
  • 81
  • [ 153936-26-6 ]
  • 3-bromo-8-methylimidazo[1,5-a]pyridine [ No CAS ]
  • 82
  • [ 153936-26-6 ]
  • 3-(2-chloropyrimidin-4-yl)-8-methylimidazo[1,5-a]pyridine [ No CAS ]
  • 83
  • [ 153936-26-6 ]
  • N-(4-fluoro-2-methoxy-5-nitrophenyl)-4-{8-methylimidazo[1,5-a]pyridin-3-yl}pyrimidin-2-amine [ No CAS ]
  • 84
  • [ 153936-26-6 ]
  • N-(4-(N,N,N'-trimethyl-1,2-ethanediamine-1-yl)-2-methoxy-5-nitrophenyl)-4-{8-methylimidazo[1,5-a]pyridin-3-yl}pyrimidin-2-amine [ No CAS ]
  • 85
  • [ 153936-26-6 ]
  • N-(4-(N,N,N'-trimethyl-1,2-ethanediamine-1-yl)-2-methoxy-5-aminophenyl)-4-{8-methylimidazo[1,5-a]pyridin-3-yl}pyrimidin-2-amine [ No CAS ]
  • 86
  • [ 153936-26-6 ]
  • N-(4-(N,N,N'-trimethyl-1,2-ethanediamine)-2-methoxy-5-acrylamidophenyl)-4-{8-methylimidazo[1,5-a]pyridin-3-yl}pyrimidin-2-amine [ No CAS ]
  • 87
  • [ 153936-26-6 ]
  • [ 1070791-30-8 ]
  • 88
  • [ 153936-26-6 ]
  • [ 1070791-01-3 ]
  • 89
  • 4-amino-2-(2-furyl)-6-methoxypyrimidine-5-carboxylic acid [ No CAS ]
  • [ 153936-26-6 ]
  • 4-amino-2-(2-furyl)-6-methoxy-N-[(3-methyl-2-pyridyl)methyl]pyrimidine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 17h; (3-Methyl-2-pyridyl)methanamine (45 mI_, 0.38 mmol), HATU (190 mg, 0.5 mmol) and then DIPEA (218 mI_, 1.25mmol) were added in quick succession to a solution of 4- amino-2-(2-furyl)-6-methoxy-pyrimidine-5-carboxylic acid (step 3)(59 mg, 0.25 mmol) in DMF (3 ml_) and the mixture stirred at room temperature for 17 hours. The resulting mixture was diluted with EtOAc (25 ml_) and washed with 50% brine (4 x 25 ml_). The organic portion was dried over MgSCL and concentrated in vacuo to afford a grey residue. Purification by column chromatography on silica eluting with a gradient of 50 to 100% EtOAc in petrol afforded a cream solid. The material was triturated with (1466) Et20/EtOAc to afford the titled compound as a pale cream solid. (1467) LC-MS (Method 8B): Rt 4.54 mins; MS m/z 340.1 = [M+H]+ (1468) 1 H NMR (500 MHz, Chloroform-d) d 9.72 - 9.65 (m, 1 H), 9.40 (br s, 1 H), 8.48 - 8.43 (m, 1 H), 7.61 (dd, J = 1.8, 0.9 Hz, 1 H), 7.57 (br d, J = 7.5 Hz, 1 H), 7.31 (d, J = 3.4 Hz, 1 H), 7.23 (br t, J = 6.3 Hz, 1 H), 6.55 (dd, J = 3.4, 1.7 Hz, 1 H), 5.73 (br s, 1 H), 4.69 (d, J = 4.1 Hz, 2H), 4.24 (s, 3H), 2.40 (s, 3H).
  • 90
  • 5-amino-3-(2-furyl)-1,2,4-triazine-6-carboxylic acid [ No CAS ]
  • [ 153936-26-6 ]
  • 5-amino-3-(2-furyl)-N-[(3-methyl-2-pyridyl)methyl]-1,2,4-triazine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h; To a solution of 5-amino-3-(2-furyl)-1 ,2,4-triazine-6-carboxylic acid (step 1 ) (28 mg, 0.14 mmol) in DMF (1 ml_) was added <strong>[153936-26-6](3-methyl-2-pyridyl)methanamine</strong> (24 pL, 0.2 mmol), HATU (103 mg, 0.27 mmol) and DIPEA (118 mI_, 0.68 mmol). The mixture was stirred at room temperature for 1 h and the resulting mixture partitioned between EtOAc (10 ml_) and hhO (10 ml_). The organic portion was separated and the aqueous further extracted with EtOAc (2 x 10 ml_). The combined organic extracts were washed with hhO (3 x 10 ml_), brine, dried over MgS04 and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 70% EtOAc in petrol afforded the titled compound as a cream solid. (1187) LC-MS (Method 8B): 3.63 mins; MS 311.1 = [M+H]+ (1188) 1 H NMR (500 MHz, Chloroform-d) d 9.65 (br t, J = 4.4 Hz, 1 H), 8.79 (br s, 1 H), 8.44 (dd, J = 4.9, 1.7 Hz, 1 H), 7.69 (dd, J = 1.8, 0.8 Hz, 1 H), 7.54 (dd, J = 3.5, 0.8 (1189) Hz, 1 H), 7.52 - 7.49 (m, 1 H), 7.17 (dd, J = 7.6, 4.9 Hz, 1 H), 6.63 (dd, J = 3.5, 1.8 (1190) Hz, 1 H), 5.84 (br s, 1 H), 4.71 (d, J = 4.4 Hz, 2H), 2.35 (s, 3H).
  • 91
  • 4-amino-2-(2-furyl)pyrimidine-5-carboxylic acid [ No CAS ]
  • [ 153936-26-6 ]
  • 4-amino-2-(2-furyl)-N-[(3-methyl-2-pyridyl)methyl]pyrimidine-5-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 0.25h; To a suspension of 4-amino-2-(2-furyl)pyrimidine-5-carboxylic acid (step 2) (88 mg, 0.43 mmol) in DMF (3 ml_) was added <strong>[153936-26-6](3-methyl-2-pyridyl)methanamine</strong> (77 pL, 0.65 mmol), HATU (326 mg, 0.86 mmol) and DIPEA (374 mI_, 2.15mmol) in quick succession and the mixture stirred at room temperature for 15 mins. The resulting mixture was diluted with EtOAc (25 ml_), washed with 50% brine (4 x 25 ml_), dried over MgS04 and the solvent removed in vacuo. Purification by column chromatography on silica eluting with a gradient of 0.5 to 4% MeOH in DCM afforded a solid which was triturated with CHCl3/Et20/Et0Ac to afford the titled compound as an off-white solid. (1206) LC-MS (Method 8B): Rt 3.31 mins; MS m/z 310.2 = [M+H]+ (1207) 1 H NMR (500 MHz, Chloroform-d) d 8.78 (s, 1 H), 8.51 - 8.45 (m, 1 H), 8.40 (dd, J = 4.9, 1 .5 Hz, 1 H), 7.62 (dd, J = 1 .7, 0.9 Hz, 1 H), 7.53 (ddd, J = 7.6, 1 .7, 0.9 Hz, (1208) 1 H), 7.32 (dd, J = 3.5, 0.9 Hz, 1 H), 7.19 (dd, J = 7.6, 4.8 Hz, 1 H), 7.03 (br s, 2H), 6.57 (dd, J = 3.5, 1 .7 Hz, 1 H), 4.63 (d, J = 3.8 Hz, 2H), 2.34 (s, 3H).
  • 92
  • 5-amino-3-(3-fluorophenyl)-1,2,4-triazine-6-carboxylic acid [ No CAS ]
  • [ 153936-26-6 ]
  • 5-amino-3-(3-fluorophenyl)-N-[(3-methyl-2-pyridyl)methyl]-1,2,4-triazine-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 1h; To a solution of 5-amino-3-(3-fluorophenyl)-1 ,2,4-triazine-6-carboxylic acid (step 1 )(18 g, 0.08 mmol) in DMF (1 ml_) was added commercially available (3-methyl-2- pyridyl)methanamine (14 mI_, 0.12 mmol), HATU (58 mg, 0.15mmol) and DIPEA (67 mI_, 0.38 mmol) and the mixture was stirred at room temperature for 1 hour. The mixture was partitioned between EtOAc (10 ml_) and H20 (10 ml_), the organic separated and the aqueous further extracted with EtOAc (2 x 10 ml_). The combined organic extracts were washed with brine, dried over MgS04 and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 20% EtOAc in hexane afforded a yellow solid. The material was suspended in Et20 and filtered to afford the titled compound as a yellow solid. (1306) LC-MS (Method 8B): Rt 4.53 mins; MS m/z 339.2 = [M+H]+ (1307) 1 H NMR (500 MHz, Chloroform-d) d 9.69 (br t, J = 4.4 Hz, 1 H), 8.74 (br s, 1 H), 8.46 (dd, J = 4.8, 1.0 Hz, 1 H), 8.34 - 8.27 (m, 1 H), 8.19 (ddd, J = 10.2, 2.7, 1.5 Hz, 1 H), 7.53 - 7.44 (1308) (m, 2H), 7.24 (tdd, J = 8.3, 2.7, 1.0 Hz, 1 H), 7.17 (dd, J = 7.6, 4.8 Hz, 1 H), 5.70 (br s, 1 H), (1309) 4.72 (d, J = 4.4 Hz, 2H), 2.36 (s, 3H).
  • 93
  • [ 917878-65-0 ]
  • [ 153936-26-6 ]
  • 3-(1-methyl-1H-pyrazol-4-yl)-7-[(3-methylpyridin-2-yl)methyl]amino}-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one [ No CAS ]
Same Skeleton Products
Historical Records

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