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CAS No. : | 21717-29-3 | MDL No. : | MFCD00218265 |
Formula : | C7H10N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JXKAUUVMXZIJNZ-UHFFFAOYSA-N |
M.W : | 122.17 | Pubchem ID : | 89021 |
Synonyms : |
|
Num. heavy atoms : | 9 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.29 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 38.41 |
TPSA : | 38.91 Ų |
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) : | -6.09 cm/s |
Log Po/w (iLOGP) : | 1.49 |
Log Po/w (XLOGP3) : | 1.34 |
Log Po/w (WLOGP) : | 1.23 |
Log Po/w (MLOGP) : | 0.89 |
Log Po/w (SILICOS-IT) : | 1.41 |
Consensus Log Po/w : | 1.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.87 |
Solubility : | 1.65 mg/ml ; 0.0135 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.76 |
Solubility : | 2.13 mg/ml ; 0.0174 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.41 |
Solubility : | 0.474 mg/ml ; 0.00388 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.41 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydroxylamine hydrochloride; In ethanol; water; at 100℃; for 8h; | The product from Example 8a (4.93 g, 0.025 mol) was dissolved in a mixture ofEtOH (80 mL) and water (30 mL). To this was added hydroxylamine hydrochloride (8.6 g, 0.123 mol) and the resulting mixture heated to 1000C for 8 h. The reaction mixture was poured into dilute sodium hydroxide solution and the crude product isolated by extraction with CH2Cl2 and dried over MgSpsi4filtered and concentrated under vacuum giving the title compound. The material was used as isolated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 136 3-[4-(3,5-Dichloropyrid-4-ylcarboxamido)phenyl]-2-(6-ethylpyrid-2-ylamino)propanoic acid 2-Amino-6-ethylpyridine gave the title compound (2.4 mg) HPLC-MS Retention time 2.14 min; MH+ 459. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 10 - 20℃; for 2.25h; | To a mixture of <strong>[21717-29-3]6-ethylpyridin-2-amine</strong> (2.00 g, 16.3 mmol) in N,N- dimethylformamide (20 mL) at 10 °C was added N-bromosuccinimide (5.80 g, 32.6 mmol) portion wise over a period of 15 min and the reaction was stirred at room temperature for 2 h. After this time, the reaction was poured into ice-cold water (100 mL) and extracted with ethyl acetate (2 chi 50 mL). The combined organic layers were washed with water (2 x 25 mL) and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (silica, gradient, hexane to ethyl acetate) to afford 3,5-dibromo-6- ethylpyridin-2-amine as a yellow crystalline solid: 1H NMR (400 MHz, CDC13) d 7.37 (s, 1 H), 4.85 (bs, 2H), 2.76 (q, J = 7.6 Hz, 2H), 1.22 (t, J = 7.6 Hz, 3H). | |
With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 10 - 20℃; for 2h; | Preparation of 3,5-dibromo-<strong>[21717-29-3]6-ethylpyridin-2-amine</strong> To a mixture of <strong>[21717-29-3]6-ethylpyridin-2-amine</strong> (2.00 g, 16.3 mmol) in N,N-dimethylformamide (20 mL) at 10° C. was added N-bromosuccinimide (5.80 g, 32.6 mmol) portion wise over a period of 15 min and the reaction was stirred at room temperature for 2 h. After this time, the reaction was poured into ice-cold water (100 mL) and extracted with ethyl acetate (2*50 mL). The combined organic layers were washed with water (2*25 mL) and dried over anhydrous sodium sulfate. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified by chromatography (silica, gradient, hexane to ethyl acetate) to afford 3,5-dibromo-<strong>[21717-29-3]6-ethylpyridin-2-amine</strong> as a yellow crystalline solid: 1H NMR (400 MHz, CDCl3) d 7.37 (s, 1H), 4.85 (bs, 2H), 2.76 (q, J=7.6 Hz, 2H), 1.22 (t, J=7.6 Hz, 3H). | |
With N-Bromosuccinimide; In dichloromethane; at 20℃; for 0.166667h; | Step A; A mixture OF 18. 8G OF 6-ETHYL-PYRIDIN-2-YLAMINE in 400 ml CHSC IS added NBS (55. 32G) portionwise at room temperature. After addition, the resulting mixture is stirred at room temperature for 10 min before it is washed with water and brine. The resulting organic phase is dried, evaporated and purified by column chromatography (HEXANE/ETOAC=7/1) to give desired product 3, 5-dibromo-<strong>[21717-29-3]6-ethyl-pyridin-2-ylamine</strong>. m/z 281. 0 (M+H) +. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.5% | With N-Bromosuccinimide; In chloroform; at 0 - 25℃; for 0.5h; | To a solution of <strong>[21717-29-3]6-ethylpyridin-2-amine</strong> (1.8 g, 15.1 mmol) in CHC13 (50.0 mL) was added NBS (2.7 g, 15.1 mmol) at 0C. The mixture was stirred at 25C for 0.5 h. The reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography (S1O2) to give 5-bromo-<strong>[21717-29-3]6-ethylpyridin-2-amine</strong> (3 g, 14.7 mmol, 97.5% yield). M+H= 201.0 (LCMS); ?HNMR (400MHz, DMSO-d6) 5 7.43 (d, J 8.6 Hz, 1H), 6.22 (d, J 8.6 Hz, 1H), 6.03 (s, 2H), 2.62 (q, J7.6Hz, 2H), 1.15 - 1.08 (m, 3H). |
83% | With N-Bromosuccinimide; In chloroform; for 0.5h;Inert atmosphere; Cooling with ice; | Compound 9: 5-Bromo-<strong>[21717-29-3]6-ethyl-pyridin-2-ylamine</strong>. Under inert condition, to a solution <strong>[21717-29-3]6-amino-2-ethylpyridine</strong> (110 mg, 1.0 equiv.) in Chloroform (4.1 mL) cooled by an ice bath, NBS (147 mg, 1.0 equiv.) was added in 3 portions. The light yellow mixture was stirred for 30 minutes, and then concentrated. Purification by flash-chromatography (AcOEt in cyclohexane, 40%) afforded compound 9 as a yellow solid in 83% yield. 1H-NMR (400 MHz, DMSO): 1.13 (t, J 7.5 Hz, 3H, CH2-CH3); 2.63 (q, J 7.5 Hz, 2H, CH2-CH3); 6.03 (bs, 2H, NH2); 6.23 (d, J 8.7 Hz, 1H, Ar); 7.44 (d, J 8.7 Hz, 1H, Ar). M/Z (M[79Br]+H)+ = 201.0. |
83% | With N-Bromosuccinimide; In chloroform; for 0.5h; | Under inert condition, to a solution <strong>[21717-29-3]6-amino-2-ethylpyridine</strong> (11 0 mg, 1.0 equiv.) in Chloroform (4.1 ml) cooled by an ice bath, NBS (147 mg, 1.0 equiv.) was added in 3 portions. The light yellow mixture was stirred for 30 minutes, and then concentrated. Purification by flash chromatography (AcOEt in cyclohexane, 40%) afforded compound 9 as a yellow solid in 83% yield.10 1H-NMR (400 MHz, DMSO): 1.13 (t, J 7.5 Hz, 3H, CHrCH3); 2.63 (q, J 7.5 Hz, 2H, CH2-CH3); 6.03 (bs, 2H, NH2); 6.23 (d, J 8.7 Hz, 1H, Ar); 7.44 (d, J 8.7 Hz, 1H, Ar). M/Z (M[79Br]+H)+ =201.0. |
78% | With N-Bromosuccinimide; In chloroform; at 0℃; for 1h; | 2-Amino-6-ethylpyridine (3.0 g, 24.6 mmol) was dissolved in chloroform (25 mL) and cooled to 0 C. NBS (4.4 g, 24.6 mmol) was added portion-wise over 30 min and the mixture was stirred for 30 min at 0 C. The solvent was removed in vacuo and the residue was slurried with EtOAc (8 mL). The resultant solids were removed by filtration through a pad of diatomaceous earth and filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography (EtOAc/hexanes) to afford 5-bromo-<strong>[21717-29-3]6-ethylpyridin-2-amine</strong> (3.83 g, 78%) as a white solid. H NMR (400 MHz, DMSO-i: delta 7.42 (d, J= 8.6 Hz, 1 H), 6.20 (d, J= 8.7 Hz, 1 H), 6.03 (s, 2 H), 2.60 (q, J= 7.5 Hz, 2 H), 1.10 (t, J= 7.5 Hz, 3 H); MS (ESI) m/z: 201.0/203.0 (M+H+). |
78% | With N-Bromosuccinimide; In chloroform; for 1.25h; | Example A17 A 0 C. solution of <strong>[21717-29-3]2-amino-6-ethylpyridine</strong> (3.00 g, 24.56 mmol) in CHCl3 (25 mL) was treated portion-wise with NBS (4.37 g, 24.56 mmol) over 30 minutes, stirred for 45 minutes, then concentrated to dryness. The residue was treated with EtOAc, the solids removed via filtration and the filtrate concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 5-bromo-<strong>[21717-29-3]6-ethylpyridin-2-amine</strong> (3.83 g, 78%) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta 7.42 (d, J=8.6 Hz, 1H), 6.20 (d, J=8.7 Hz, 1H), 6.03 (s, 2H), 2.60 (q, J=7.5 Hz, 2H), 1.10 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 203.0 (M+H+). |
68% | With N-Bromosuccinimide; In chloroform; at 0℃; for 1.25h; | A 0 C. solution of <strong>[21717-29-3]6-ethylpyridin-2-amine</strong> (3.37 g, 27.6 mmol) in CHCl3 (30 mL) was treated portion-wise with NBS (4.91 g, 27.6 mmol) over 30 min, stirred for 45 min, then concentrated to dryness. The residue was treated with EtOAc (8 mL), filtered to remove solids and purified via silica gel chromatography (EtOAc/Hex) to afford 5-bromo-<strong>[21717-29-3]6-ethylpyridin-2-amine</strong> (3.79 g, 68%). 1H NMR (400 MHz, DMSO-d6): delta 7.43 (d, J=8.6 Hz, 1H), 6.21 (d, J=8.7 Hz, 1H), 6.03 (s, 2H), 2.61 (q, J=7.5 Hz, 2H), 1.11 (t, J=7.5 Hz, 3H); MS (ESI) m/z: 201.0 (M+H+). |
With N-Bromosuccinimide; In chloroform; at 0℃; for 0.5h; | Step A; To a solution of 2-amino-6-ethyl-pyridine (50 g) in chloroform (250 mL) is added NBS (73 g) at 0 C over 30 min. The mixture is stirred for additional 30 min and is directly purified by flash column chromatography on silica gel to give 5-bromo-<strong>[21717-29-3]6-ethyl-pyridin-2-ylamine</strong> as white solid. Rf (hexane: EtOAc = 4: 1) = 0.34. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With triethylamine; In dichloromethane; ethyl acetate; | Part 5 N-(6-Ethyl-pyridin-2-yl)-2,2-dimethyl-propionamide A solution of <strong>[21717-29-3]6-ethyl-pyridin-2-ylamine</strong> (20 g, 0.164 mol) and triethylamine (29.6 mL, 0.213 mol) in dichloromethane (200 mL, 0.8 M) is cooled to 0° C. and carefully treated with pivaloyl chloride (26.2 mL, 0.213 mol). After stirring for 2 h, the solution is quenched with aq NaHCO3, extracted with dichloromethane and concentrated. The resulting oil is filtered through a plug of silica gel using ethyl acetate. The filtrate is concentrated and triturated with heptane to give N-(6-ethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (18.3 g, 54percent) as a white crystalline solid. mp 59-62° C.; Rf 0.31 (25percent ethyl acetate in hexanes); 1H NMR (DMSO-d6, 300 MHz) delta9.56 (s, 1 H), 7.85 (d, J=8.4 Hz, 1 H), 7.63 (t, J=7.8 Hz, 1 H), 6.93 (d, J=7.5 Hz, 1 H), 2.65 (q, J=7.8 Hz, 2 H), 1.20 (s, 9 H), 1.18 (t, 7.8 Hz, 3 H); LRMS calcd for C12H18N2O: 206.2; found 206.0 (M)+. Anal. Calcd for C12H18N2O: C, 69.87; H, 8.80; N, 13.58. Found C, 69.60; H, 8.67; N, 13.42. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; methanol; dichloromethane; water; methanesulfonyl chloride; | 1.56 cm3 of methylsulfonyl chloride are poured dropwise into a solution, cooled to +5° C., of 2.50 g of <strong>[21717-29-3]2-amino-6-ethylpyridine</strong> in 2.50 cm3 of pyridine. After stirring for 20 hours at 20° C., the reaction mixture is supplemented with 8 cm3 of water and filtered. The filtrate is concentrated to dryness at 50° C. under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.040-0.063 mm, height 30 cm, diameter 4 cm), eluding under an argon pressure of 0.5 bar with 1.5 liters of dichloromethane and then with a mixture of dichloromethane and methanol (98/2 by volume) and collecting 60-cm3 fractions. Fractions 8 to 12 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 2.8 g of N-(6-ethylpyrid-2-yl)methylsulfonamide are obtained in the form of a yellow oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 6AMethod BPreparation of compound 1016Step 1 : A mixture of benzylchloride 4a12 (56 mg, 0.1 mmol), <strong>[21717-29-3]2-amino-6-ethylpyridine</strong> (18 mg, 0.15 mmol), Cs2CO3 (50 mg, 0.15 mmol), Kl (6 mg, 0.04 mmol) and MgSO4 (70 mg, 0.58 mmol) in DMF (1 rmL) is agitated on a J-Kem.(R). orbital shaker (300 rpm) at 700C overnight. The mixture is cooled to ambient temperature, filtered and washed with DMSO (0.5 ml_). Aqueous NaOH (5 N, 0.2 ml_, 1.0 mmol) is added and the mixture is agitated on a Bohdan orbital shaker (300 rpm) at RT for 2 hours. The mixture is acidified with AcOH, then purified by preparative HPLC to isolate compound 1016. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 20℃; for 8h;Cooling with ice; | (1) phenyl (6-ethylpyridin-2-yl)carbamate To a solution of <strong>[21717-29-3]6-ethylpyridin-2-amine</strong> (1 g) in tetrahydrofuran (20 mL) was added phenyl chloride carbonate (1.2 mL) under ice-cooling, and the mixture was stirred at room temperature for 8 hr. Saturated aqueous sodium hydroxide solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was washed with diisopropyl ether to give the object product (0.8 g) as a white solid. 1H NMR (300 MHz, CDCl3) delta ppm 1.28 (t, J=7.2 Hz, 3H) 2.73 (q, J=7.2 Hz, 2H) 6.89 (d, J=6.9 Hz, 1H) 7.09-7.42 (m, 5H) 7.61 (t, J=7.5 Hz, 1H) 7.76 (d, J=8.4 Hz, 1H) 7.89 (brs, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | Intermediate 40: 6-ethyl-3-nitro-2-pyridinamine To an ice-cooled solution of 6-ethyl-2-pyridinamine (5g, 40.9mmol) in concentrated sulfuric acid (97percent) (2OmL, 375mmol) was slowly added concentrated nitric acid (70percent) (1.9mL, 42.5mmol). The cooling was removed and the mixture allowed to warm to about 5O0C under a mild exotherm (some bubbling ; frothing observed). After the exotherm had subsided the mixture was stirred at ambient temperature and was allowed to stand overnight. The mixture was then poured carefully into stirred, crushed ice (about 50OmL). The resulting solution was treated with aqueous sodium hydroxide (10M) until pH 4-5 was achieved. The precipitated solid was filtered off, washed with water and dried. The product was purified by flash chromatography on silica using a gradient elution from 0 to 100percent ethyl acetate in cyclohexane to afford the title compound (1.7g, 10.2mmol, 25percent yield) (as well as 2.6g of the later-eluting isomeric by-product, 6-ethyl-5-nitro-2- pyridinamine). LCMS (Method A): Rt 0.76minutes; m/z 168 (MH+). 1 H NMR (400MHz, MeOD) delta 1.25 (t, J=7.65Hz, 3H), 2.69 (q, J=7.70Hz, 2H), 6.64 (d, J=8.53Hz, 1 H), 8.33 (d, J=8.53Hz, 1 H). (The amine functionality was not seen in this NMR spectrum due to proton exchange with the solvent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine; In dichloromethane; at 20℃; for 1h; | General Procedure: Compound 7a was prepared from 3-cyano-5-fluorobenzoic acid (900 mg, 5.45 mmol), stirred at reflux in SOCl2 (15 mL) for 2 h, followed by removal of excess thionyl chloride. The residue was taken up in CH2Cl2 (2 mL) and added to a solution of 6-methylpyridin-2-amine (6a, 638 mg, 5.9 mmol) in CH2Cl2 (9 mL), DMF (2 drops) followed by addition of TEA (1.65 mL) at 0 OC. The reaction mixture was stirred at r. t. overnight and then diluted with H2O (15 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (3 X 15 mL). The combined organic layer was dried with Na2SO4, and concentrated. The residue was purified by flash column chromatography (Hexane/ EtOAc/TEA 2:1: 0.03) to give a yellow foam (1.39 g, 100percent); The HCl salt was made by dissolving the free base in HCl ether solution and then recrystallizing from hot MeOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In 1,4-dioxane; toluene; for 16h;Inert atmosphere; Reflux; | A mixture of 6-chloro-2-aminopyridine (15.0 g, 1 16 mmol) and [1,3- bis(diphenylphosphino)propane]nickel(II) chloride (5.70 g, 10.5 mmol) in anhydrous 1,4- dioxane (450 mL) was treated with 1.1 M solution of diethylzinc in toluene (225 mL) and the reaction stirred, under a nitrogen atmosphere, at reflux for 16 h. After this time, the reaction was cooled to room temperature, treated with methanol (200 mL) and concentrated under reduced pressure. The resulting residue was diluted in brine (500 L) and extracted with a mixture of 9: 1 methylene chloride/methanol (3 x 300 mL). The combined organic layers were dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford 6-ethylpyridin-2-amine as a brown gel, which was used in the next step without further purification: NMR (400 MHz, CDC13) d 7.36 (t, J = 7.6 Hz, 1 H), 6.53 (d, J= 7.6 Hz, 1H), 6.33 (d, J= 7.6 Hz, 1H), 4.41 (bs, 2H), 2.64 (q, J= 7.6 Hz, 2H), 1.26 (t, J= 7.6 Hz, 3H). | |
With [1,3-bis(diphenylphosphino)propane]nickel(II) chloride; In 1,4-dioxane; toluene; for 16h;Inert atmosphere; Reflux; | Example 14 Preparation of 6-ethylpyridin-2-amine A mixture of 6-chloro-2-aminopyridine (15.0 g, 116 mmol) and [1,3-bis(diphenylphosphino)propane]nickel(II) chloride (5.70 g, 10.5 mmol) in anhydrous 1,4-dioxane (450 mL) was treated with 1.1 M solution of diethylzinc in toluene (225 mL) and the reaction stirred, under a nitrogen atmosphere, at reflux for 16 h. After this time, the reaction was cooled to room temperature, treated with methanol (200 mL) and concentrated under reduced pressure. The resulting residue was diluted in brine (500 L) and extracted with a mixture of 9:1 methylene chloride/methanol (3*300 mL). The combined organic layers were dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford 6-ethylpyridin-2-amine as a brown gel, which was used in the next step without further purification: 1H NMR (400 MHz, CDCl3) d 7.36 (t, J=7.6 Hz, 1H), 6.53 (d, J=7.6 Hz, 1H), 6.33 (d, J=7.6 Hz, 1H), 4.41 (bs, 2H), 2.64 (q, J=7.6 Hz, 2H), 1.26 (t, J=7.6 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In dichloromethane; at 20℃; for 1h;Inert atmosphere; | Step 2 2-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (6-ethyl-pyridin-2-yl)-amide To a stirred solution of 2-chloro-thieno[3,2-d]pyrimidine-7-carbonyl chloride (0.054 g, 0.233 mmol) and <strong>[21717-29-3]2-amino-6-ethylpyridine</strong> (0.029 g, 0.233 mmol) methylene chloride (2 mL) was added pyridine (0.057 mL, 0.7 mmol). The reaction mixture was stirred under nitrogen at room temperature for 1 h, and then was diluted with EtOAc, washed with aqueous sodium carbonate and brine, then dried (Na2SO4), filtered and concentrated in vacuo in vacuo to give crude 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (6-ethyl-pyridin-2-yl)-amide (0.060 g, 0.189 mmol, 80.8percent) as a light yellow solid which was used directly in the next step without further purification. LCMS m/z [M+H]=319. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | In acetonitrile; at 140℃; for 72h; | Step 1 6-Chloro-4-(6-ethyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid ethyl ester 4,6-Dichloro-pyridazine-3-carboxylic acid ethyl ester (500 mg, 2.26 mmol) and <strong>[21717-29-3]6-ethylpyridin-2-amine</strong> 415 mg, 3.39 mmol) were dissolved in acetonitrile (7 mL), then heated at 140° C. for 3 d. The reaction mixture was cooled and concentrated in vacuo. Purification by chromatography (silica, 5 to 50percent ethyl acetate in hexanes) gave 6-chloro-4-(6-ethyl-pyridin-2-ylamino)-pyridazine-3-carboxylic acid ethyl ester (246 mg, 35percent) as a light brown solid. 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 10.68 (br. s., 1H) 9.30 (s, 1H) 7.61 (t, J=7.8 Hz, 1H) 6.91 (d, J=7.3 Hz, 1H) 6.77 (d, J=7.8 Hz, 1H) 4.57 (q, J=7.2 Hz, 2H) 2.86 (q, J=7.6 Hz, 2H) 1.52 (t, J=7.1 Hz, 3H) 1.38 (t, J=7.5 Hz, 3H); LCMS (EI/CI) m/z: 307 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 80℃; for 3h;Inert atmosphere; | A mixture of 5-[(li?,25)-2-aminocyclohexyl]amino}-3-bromopyridine-2-carbonitrile TFA salt (62 mg, 0.15 mmol), <strong>[21717-29-3]2-amino-6-ethylpyridine</strong> (19 mg, 0.15 mmol), Xantphos (13 mg, 0.023 mmol), Pd2(dba)3 (14 mg, 0.015 mmol), and cesium carbonate (197 mg, 0.606 mmol) was evacuated and backfilled with nitrogen (3x). Dioxane (1 mL) was added, and the reaction mixture was heated to 80°C for 3 hours. The reaction mixture was allowed to cool to room temperature, filtered, and concentrated under reduced pressure to afford 5-[(li?,2S)-2- aminocyclohexyl]amino}-3-[(6-ethylpyridin-2-yl)amino]pyridine-2-carbonitrile. The material was used without further purification in the subsequent transformation. MS ESI calc'd. for C19H25N6 [M + H]+ 337, found 337. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With triethylamine; In dichloromethane;Reflux; | General procedure: A mixture of 2-amino-6-methylpyridine (6a) (0.61g, 5.6mmol) and triethylamine (4mL) in dichloromethane (DCM) (10mL) was added dropwise to freshly made 4-propoxybenzoyl chloride (7a) (1.19g, 6.0mmol) in DCM (5mL) and the reaction mixture was heated to reflux overnight. After cooling, the mixture was washed with water, brine and dried with anhydrous MgSO4. The solvent was evaporated under reduced pressure, then the crude product was further purified on a silica gel column using hexanes/ethyl acetate (3:1) to yield the pure product (1.2g, 79percent) as a colorless solid, mp 86?89°C. 1H NMR (CDCl3, 300MHz) delta 8.59 (s, 1H), 8.19 (d, J=8.1Hz, 1H), 7.89 (d, J=8.4Hz, 2H), 7.64 (dd, J=7.8Hz, 1H), 6.96 (d, J=8.4Hz, 2H), 6.91 (d, J=7.5Hz, 1H), 3.99 (t, J=6.6Hz, 2H), 2.46 (s, 3H), 1.85 (m, 2H), 1.06 (t, J=7.2Hz, 3H); 13C NMR (CDCl3, 75MHz) delta 165.2, 162.4, 156.8, 151.1, 138.7, 129.1, 126.3, 119.2, 114.4, 110.9, 69.7, 24.0, 22.5, 10.5; ESI-MS m/z 271.11 (M+H, 100); Anal. Calcd for C16H18N2O2 (270.14): C, 71.09; H, 6.71; N, 10.36. Found: C, 70.71; H, 6.78; N, 10.06. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With triethylamine; In dichloromethane;Reflux; | General procedure: A mixture of 2-amino-6-methylpyridine (6a) (0.61g, 5.6mmol) and triethylamine (4mL) in dichloromethane (DCM) (10mL) was added dropwise to freshly made 4-propoxybenzoyl chloride (7a) (1.19g, 6.0mmol) in DCM (5mL) and the reaction mixture was heated to reflux overnight. After cooling, the mixture was washed with water, brine and dried with anhydrous MgSO4. The solvent was evaporated under reduced pressure, then the crude product was further purified on a silica gel column using hexanes/ethyl acetate (3:1) to yield the pure product (1.2g, 79percent) as a colorless solid, mp 86?89°C. 1H NMR (CDCl3, 300MHz) delta 8.59 (s, 1H), 8.19 (d, J=8.1Hz, 1H), 7.89 (d, J=8.4Hz, 2H), 7.64 (dd, J=7.8Hz, 1H), 6.96 (d, J=8.4Hz, 2H), 6.91 (d, J=7.5Hz, 1H), 3.99 (t, J=6.6Hz, 2H), 2.46 (s, 3H), 1.85 (m, 2H), 1.06 (t, J=7.2Hz, 3H); 13C NMR (CDCl3, 75MHz) delta 165.2, 162.4, 156.8, 151.1, 138.7, 129.1, 126.3, 119.2, 114.4, 110.9, 69.7, 24.0, 22.5, 10.5; ESI-MS m/z 271.11 (M+H, 100); Anal. Calcd for C16H18N2O2 (270.14): C, 71.09; H, 6.71; N, 10.36. Found: C, 70.71; H, 6.78; N, 10.06. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Parallel preparation of Examples 79 through 79d: A set of 2-dram vials were each charged with an individual requisite amine (RaNH2, 0.069 mmol). To each vial was added a solution of 19-3 (26 mg, 0.058 mmol) and iPr2NEt (0.025 mL, 0.15 mmol) in CH2C12 (1 mL) followed by T3P (50percent wt in EtOAc, 0.055 mL, 0.092 mmol). The resultant mixtures were stirred at RT overnight. After that time, additional T3P (50percent wt in EtOAc, 0.055 mL, 0.092 mmol) and iPr2NEt (0.025 mL, 0.15 mmol) were added to each vial. The mixtures were stirred at RT for an additional 24 hours. To each vial was then added water (0.050 mL) and TFA (0.50 mL). The mixtures were stirred at RT for 2 hours. The mixtures were then concentrated in vacuo (max temp = 40°C). Each crude product was re-dissolved in 1 mL of DMSO and filtered. The crude products were purified by mass triggered HPLC (Waters XBridge C18 column, 5muiotaeta, 19x100 mm, gradient ranges from 10-15percent initial to 50-55percent final MeCN (0.1percent NH4OH) in water (0.1percent NH4OH) 50 mL/min, 8 min run time) to afford Examples 79 through 79d. | ||
General procedure: Parallel preparation of Examples 79 through 79d: A set of 2-dram vials were each charged with an individual requisite amine (RaNH2, 0.069 mmol). To each vial was added a solution of 19-3 (26 mg, 0.058 mmol) and iPr2NEt (0.025 mL, 0.15 mmol) in CH2Cl2 (1 mL) followed by T3P (50percent wt in EtOAc, 0.055 mL, 0.092 mmol). The resultant mixtures were stirred at RT overnight. After that time, additional T3P (50percent wt in EtOAc, 0.055 mL, 0.092 mmol) and iPr2NEt (0.025 mL, 0.15 mmol) were added to each vial. The mixtures were stirred at RT for an additional 24 hours. To each vial was then added water (0.050 mL) and TFA (0.50 mL). The mixtures were stirred at RT for 2 hours. The mixtures were then concentrated in vacuo (max temp=40° C.). Each crude product was re-dissolved in 1 mL of DMSO and filtered. The crude products were purified by mass triggered HPLC (Waters XBridge C18 column, 5 mum, 19×100 mm, gradient ranges from 10-15percent initial to 50-55percent final MeCN (0.1percent NH40H) in water (0.1percent NH40H) 50 mL/min, 8 min run time) to afford Examples 79 through 79d. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With 4-methyl-morpholine; In water; ethyl acetate; acetonitrile; | Part A 1,1-Dimethylethyl (3R)-3-(cyclopentylmethyl)-4-(5-[(6-ethyl-2-pyridinyl)amino]carbonyl}-4,5-dihydro-1H-pyrazol-1-yl)-4-oxobutanoate To a solution of 1-{(2R)-2-(cyclopentylmethyl)-4-[(1,1-dimethylethyl)oxy]-4-oxobutanoyl}-4,5-dihydro-1H-pyrazole-5-carboxylic acid (352 mg, 1.0 mmol) in acetonitrile (10 mL) at 0° C. was added 4-[4,6-bis(methyloxy)-1,3,5-triazin-2-yl]-4-methylmorpholin-4-ium (656 mg, 2.0 mmol) and N-methylmorpholine (0.28 mL, 2.5 mmol). The reaction mixture was stirred for 2 hours. After this time, 6-ethyl-2-pyridinamine (159 mg, 1.3 mmol) was added to the mixture, which was then allowed to warm to room temperature and stirred for 3 hours. The solvent was removed under reduced pressure, and water (5 mL) and DCM (15 mL) were added to the resulting residue. The phases were separated. The aqueous phase was extracted twice with DCM (15 mL), and the combined organic phases were dried over sodium sulfate and concentrated. The crude product residue was purified by Combiflash silica gel chromatography (0-100percent EtOAc in hex) to provide 1,1-dimethylethyl (3R)-3-(cyclopentylmethyl)-4-(5-[(6-ethyl-2-pyridinyl)amino]carbonyl}-4,5-dihydro-1H-pyrazol-1-yl)-4-oxobutanoate (359 mg, 0.79 mmol, 79percent yield) as a clear oil. MS: 457 ([M+H]+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 5 (3S)-2-(2R)-3-Cyclopentyl-2-[formyl(hydroxy)amino]methyl}propanoyl)-N-(6-ethyl-2-pyridinyl)-3-pyrazolidinecarboxamide <strong>[21717-29-3]2-amino-6-ethylpyridine</strong> (84 mg, 0.67 mmol). LC/MS: (M+H)+: 417.9. 1H NMR (400 MHz, METHANOL-d4) delta ppm 1.03-1.24 (m, 2H) 1.36-1.48 (m, 1H) 1.48-1.70 (m, 4H) 1.70-2.00 (m, 4H) 2.16-2.36 (m, 1H) 2.55 (ddd, J=12.13, 6.32, 2.53 Hz, 1H) 2.83-3.01 (m, 1H) 3.15-3.31 (m, 1H) 3.51 (dd, J=13.89, 4.55 Hz, 1H) 3.59-3.86 (m, 2H) 3.96 (dt, J=9.41, 4.77 Hz, 1H) 4.70 (t, J=7.83 Hz, 1H) 6.99 (d, J=7.33 Hz, 1H) 7.67 (t, J=7.83 Hz, 1H) 7.79-7.97 (m, 2H). | ||
Example 5 (3S)-2-((2R)-3-Cyclopentyl-2-[formyl(hydroxy)amino]methyl}propanoyl)-N-(6-ethyl-2-pyridinyl)-3-pyrazolidinecarboxamide <strong>[21717-29-3]2-amino-6-ethylpyridine</strong> (84 mg, 0.67 mmol). LC/MS: (M+H)+: 417.9. 1H NMR (400 MHz, METHANOL-d4) delta ppm 1.03-1.24 (m, 2H) 1.36-1.48 (m, 1H) 1.48-1.70 (m, 4H) 1.70-2.00 (m, 4H) 2.16-2.36 (m, 1H) 2.55 (ddd, J=12.13, 6.32, 2.53 Hz, 1H) 2.83-3.01 (m, 1H) 3.15-3.31 (m, 1H) 3.51 (dd, J=13.89, 4.55 Hz, 1H) 3.59-3.86 (m, 2H) 3.96 (dt, J=9.41, 4.77 Hz, 1H) 4.70 (t, J=7.83 Hz, 1H) 6.99 (d, J=7.33 Hz, 1H) 7.67 (t, J=7.83 Hz, 1H) 7.79-7.97 (m, 2H). |
Tags: 21717-29-3 synthesis path| 21717-29-3 SDS| 21717-29-3 COA| 21717-29-3 purity| 21717-29-3 application| 21717-29-3 NMR| 21717-29-3 COA| 21717-29-3 structure
[ 99132-27-1 ]
6-Ethyl-N-methylpyridin-2-amine
Similarity: 0.88
[ 99132-27-1 ]
6-Ethyl-N-methylpyridin-2-amine
Similarity: 0.88
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