Structure of 2632-65-7
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CAS No. : | 2632-65-7 |
Formula : | C10H14N2 |
M.W : | 162.23 |
SMILES Code : | NC1=CC=C(N2CCCC2)C=C1 |
MDL No. : | MFCD00156245 |
InChI Key : | URAARCWOADCWLA-UHFFFAOYSA-N |
Pubchem ID : | 808841 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H332-H335 |
Precautionary Statements: | P280-P305+P351+P338-P310 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.4 |
Num. rotatable bonds | 1 |
Num. H-bond acceptors | 0.0 |
Num. H-bond donors | 1.0 |
Molar Refractivity | 55.49 |
TPSA ? Topological Polar Surface Area: Calculated from |
29.26 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.8 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
2.88 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.5 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.71 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.63 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.9 |
Log S (ESOL):? ESOL: Topological method implemented from |
-2.96 |
Solubility | 0.176 mg/ml ; 0.00109 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.15 |
Solubility | 0.114 mg/ml ; 0.000701 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.47 |
Solubility | 0.546 mg/ml ; 0.00337 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
Yes |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.24 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
2.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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 |
---|---|---|
85% | With palladium 10% on activated carbon; hydrogen; In ethanol; at 20℃; for 9h;Inert atmosphere; Schlenk technique; | General procedure: The nitrophenyl analogue 7a-7e (7.5 mmol) was dissolved in ethanol (50 mL), and to this solution was added 10% Pd/C (0.2 g). The reaction mixture was stirred at room temperature under an atmosphere of H2 for 9 h. After completion of the reaction, the resulting mixture was filtered through Celite. The filtrate was concentrated under high vacuum to afford the desired aniline derivatives 8a-8e. |
80% | With ammonium hydroxide; sodium dithionite; In water; for 0.25h;Reflux; | General procedure: To a solution of 1-(substituted) 4-nitrobenzene IVa,b,e,f(0.01 mol) in NH4OH (20 mL, 30%), a solution of sodium dithionite(7 g, 0.04 mol) in water (30 mL) was quickly added, the reactionmixture was refluxed for 15 min. After cooling, the crude productwas filtered, washed and crystallized from methylene chloride toyield target compounds Va,b,e,f. 4-(Pyrrolidin-1-yl) aniline Vb Yield 80% as yellow oil, (as reported) [66] . |
59.28% | With iron; ammonium chloride; In ethanol; water; at 90℃; | To a stirred solution of 580 1-(4-nitrophenyl)pyrrolidine (0.60 g, 3.121 mmol, 1.0 eq) in 6 EtOH (20 mL) was added Fe(0) (1.395 g, 24.971 mmol, 8.0 eq) and a solution of 67 NH4Cl (1.67 g, 31.210 mmol, 10.0 eq) at rt. The resulting mixture was heated at 90 C. for 60 min. The progress of reaction was monitored by LCMS. The reaction mixture was filtered through celite the residue was washed with EtOH (50 mL) the filtrate was concentrated and the residue was dissolved in 19 EtOAc (50 mL), washed with water (2×50 mL), dried over Na2SO4, and concentrated to afford 583 4-(pyrrolidin-1-yl)aniline (0.30 g, 59.28%) as brown viscous. (0608) LCMS: 163.3 [M+1]+ |
55% | With sodium hydroxide;Pd on carbon; In ethanol; acetic acid; ethyl acetate; | 2) 4-(Pyrrolidin-1-yl)-phenylamine (8). To a solution of 7 in ethanol (20 mL) was added 10 wt % Pd on carbon (Degussa) (25 mg, 23 mol). Glacial acetic acid (2-3 drops) was added to the reaction. The reaction was placed under a H2 atmosphere and stirred for 16 hours, after which the reaction mixture was filtered through a pad of celite. The filtrate was evaporated, and the residue then dissolved in ethyl acetate (20 mL) and washed with 2N HCl (aq. 15 mL). The aqueous phase was isolated and then basified by the addition of 2N NaOH (aq. 20 mL). The aqueous layer was extracted with ethyl acetate (20 mL*2). The ethyl acetate extracts were dried over anhydrous magnesium sulfate, filtered, and evaporated to give crude 8 as a yellow oil (642 mg, 55% for 2 steps). |
With hydrogen; In ethyl acetate; at 50℃; under 7500.75 Torr; | l-(4-nitrophenyl)pyrrolidine was dissolved in ethyl acetate (0.05 M) and reduced with H-cube at 50C, 10 bar. Reduction was completed in 2 cycles. The solvent was evaporated off in vacuo, and the crude purified using column chromatography to afford the product. 1H NMR (400 MHz, DMSO-d6) 6 (ppm): 6.49 (d, J=8.4 Hz, 2H), 6.34 (d, J-8.4 Hz), 4.24 (s, 2H), 3.07 (m, 4H), 1.87 (m, 4H). LC-MS: m/z 163 (M+H). | |
With palladium 10% on activated carbon; hydrogen; In methanol; at 20℃; | General procedure: A suspension of 1.01 g (5 mmol) 1-bromo-4-nitrobenzene, 1.5 g K2CO3, 0.59 mL (6 mmol) piperidine in 10 mL of DMF was heated to reflux overnight. Upon cooling, the reaction mixture was dilute with water, extracted with EA, and the organic layer was washed with water, followed by saturated NaCl aqueous solution, dried over anhydrous Na2SO4 and purified by flash chromatography (PE : EA = 50:1, 30:1) to afford 902 mg (87%) yellow solid. The solid was dissolved in methanol, 90 mg Pd-C (10%) was added and stirred under hydrogen overnight at room temperature and then filtered through Celite and concentratedin vacuo. The crude product was purified by flash chromatography (PEEA = 5:1) to afford 4l? 0.706 g 99%. | |
With 5%-palladium/activated carbon; hydrogen; In ethanol; water; at 20℃; | General procedure: The substituted nitro compound 11 (1 equiv in a mixture of EtOH-H2O, 95:5, 20mL) was treated with 10% Pd-carbon (5% w/w). The reaction was subjected to hydrogenation under hydrogen gas at room temperature and the reaction was monitored by TLC. After completion of the reaction, the mixture was filtered through a Celite bed and concentrated in a vacuum to afford product 12. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | General procedure: To a flame-dried 25 mL round bottom flask was charged activated Mg (7.5 mmol, 1.5 eq.) and 5 mL anhydrous THF. To this suspension was added 2 drops of 1,2-dibromoethane. After 5 min, a solution of Aryl bromide (5 mmol, 1.0 eq.) in 5 mL anhydrous THF was slowly added to the suspension of Mg at room temperature. The reaction was mildly exothermic. The Grignard reagent was titrated and 1 mmol of this reagent was added to a flame-dried reaction vial. The solution was diluted with 3 mL anhydrous toluene and after cooling to the target temperature T, a solution of oxaziridine (1.2 mmol, 1.2 eq.) in 1 mL anhydrous toluene was added. The reaction was maintained at the targeted temperature T for time t before being quenched with saturated aqueous NH4Cl. (The actual temperature/reaction time is listed for each substrate.) | |
The following 4-substituted anilines were prepared: 4-azocan-1-ylphenylamine N-cyclohexyl-N-methylbenzene-1,4-diamine 4-pyrrolidin-1-ylphenylamine 4-(2,5-dimethylpyrrolidin-1-yl)phenylamine 4-(3,6-dihydro-2H-pyridin-1-yl)phenylamine ... | ||
Representative examples of suitable p-phenylenediamine compounds are: 4-N,N-dimethylamino aniline, 4-N,N-diethylamino aniline, 4-(N-ethyl,N-hydroxyethyl)amino aniline, ... 2,6-dimethyl,4-(N,N-dihydroxyethyl)amino aniline, 2,3,5,6-tetramethyl-4-N,N-diethylamino aniline, 4-piperidino aniline, 4-morpholino aniline, 4-pyrrolidyl aniline, 4-imidazolo aniline. |
Representative examples of suitable p-phenylenediamine compounds are: ... 2,6-dimethyl,4-(N,N-dihydroxyethyl)amino aniline, 2,3,5,6-tetramethyl-4-N,N-diethylamino aniline, 4-piperidino aniline, 4-morpholino aniline, 4-pyrrolidyl aniline, 4-imidazolo aniline. | ||
With hydroxylamine hydrochloride; sodium hydroxide; In water; at 20 - 100℃; for 5h; | General procedure: To a stirred solution of the corresponding 3-phenyl-3-oxopropanenitrile (1 equiv.) in water (0.7M) was added aqueous sodium hydroxide (2 equiv.) solution and hydroxylamine hydrochloride (1.1 equiv.) at room temperature. The resulting reaction mixture was stirred at 100 C for 5 h. After completion of starting material, the reaction mixture was cooled to room temperature and precipitated solid was collected by filtration and dried to give the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | With triethylamine; In N,N-dimethyl-formamide; acetonitrile; at 120℃; for 1h;Microwave irradiation; | Example 16; 2-felambdaf-ButyI-5-phenyl-4-[(4-pyrrolidin-l-ylphenyl)amino]isothiazoI-3(2H)-one 1,1-dioxide; A mixture of 2-t°rt-butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.150g, 0.500mmol), (4-pyrrolidin-l-ylrhohenyl)amine (0.08 Ig, 0.500mmol) and TEA (0.070ml, 0.500mmol) in MeCN (2ml) and DMF (ImI) was heated in a microwave reactor at 120C for 45mins. TEA (0.070ml, 0.500mmol) was added and the mixture was heated at 120C for 5 15mins. The precipitate from the reaction mixture was isolated by filtration and washed with MeCN. The crude product was dissolved in MeOH and purified by silica gel column chromatography using 15-100% EtOAc in petroleum ether 40-60C as eluent, to give the title compound (0.146g, 69%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 20℃; for 1h; | a. (4-Pyrrolidin-1-yl-phenyl)-carbamic acid 4-nitro-phenyl ester hydrochloride To a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin-1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THF. After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2*10 mL) and then with anhydrous DCM (3*10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, 1H), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 3.86-3.68 (bs, 4H), 2.35-2.24 (bs, 4H). LC/MS (ESI): 328 (MH)+. | |
In tetrahydrofuran; at 20℃; for 1h; | To a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin-1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THF. After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2*10 mL) and then with anhydrous DCM (3*10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, 1H), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 3.86-3.68 (bs, 4H), 2.35-2.24 (bs, 4H). LC/MS (ESI): 328 (MH)+. | |
To a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin-1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THF. After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2*10 mL) and then with anhydrous DCM (3*10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, 1H), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 3.86-3.68 (bs, 4H), 2.35-2.24 (bs, 4H). LC/MS (ESI): 328 (MH)+. |
In tetrahydrofuran; at 20℃; for 1h; | a. (4-Pyrrolidin-1-yl-phenyl)-carbamic acid 4-nitro-phenyl ester hydrochloride To a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin-1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THF. After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2*10 mL) and then with anhydrous DCM (3*10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, 1H), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 3.86-3.68 (bs, 4H), 2.35-2.24 (bs, 4H). LC/MS (ESI): 328 (MH)-. | |
In tetrahydrofuran; at 20℃; for 1h; | To a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin-1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THF. After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2*10 mL) and then with anhydrous DCM (3*10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, 1H), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 3.86-3.68 (bs, 4H), 2.35-2.24 (bs, 4H). LC/MS (ESI): 328 (MH)+. | |
In tetrahydrofuran; at 20℃; for 1h; | To a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin-1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THF. After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2*10 mL) and then with anhydrous DCM (3*10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, 1H), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 3.86-3.68 (bs, 4H), 2.35-2.24 (bs, 4H). LC/MS (ESI): 328 (MH)+. | |
In tetrahydrofuran; at 20℃; for 1h; | EXAMPLE 74; 4-{7-[2-(2-Oxo-pyrrolidin-1-yl)-ethoxy]-quinazolin-4-yl}-piperidine-1-carboxylic acid (4-pyrrolidin-1-yl-phenyl)-amide; a). (4-Pyrrolidin-1-yl-phenyl)-carbamic acid 4-nitro-phenyl ester hydrochloride; To a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin-1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THF. After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2×10 mL) and then with anhydrous DCM (3×10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, 1H), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 3.86-3.68 (bs, 4H), 2.35-2.24 (bs, 4H). LC/MS (ESI): 328 (MH)+. | |
In tetrahydrofuran; at 20℃; for 1h; | EXAMPLE NO. 49; 1-[1-(6,7-Dimethoxy-quinazolin-4-yl)-pyrrolidin-3-yl]-3-(4-pyrrolidin-1-yl-phenyl)-urea (Compound No. 49); a. (4-Pyrrolidin-1-yl-phenyl)-carbamic acid 4-nitro-phenyl ester hydrochloride; To a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin-1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THF. After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2×10 mL) and then with anhydrous DCM (3×10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, 1H), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 (d, 2H), 7.48 (d, 2H), 3.86-3.68 (bs, 4H), 2.35-2.24 (bs, 4H). LC/MS (ESI): 328 (MH)-. | |
In tetrahydrofuran; at 20℃; for 1h; | Example 18; 4-[6-Amino-5-(methoxyimmo-methyl)-pyrimidin-4-yl]-piperazine-l-carboxylic acid (4-pyrrolidin- 1 -yl-phenyl)-amide; a. (4-Pyrrolidin- 1 -yl-phenyl)-carbamic acid 4-nitro-phenyl ester hydrochlorideTo a stirred solution of 4.9 g (30.4 mmol) of 4-pyrrolidin- 1-yl-phenylamine in 70 mL of anhydrous THF at room temperature, was added dropwise a solution of 6.4 g (32 mmol) of 4-nitrophenyl chloroformate in 16 mL of anhydrous THE After the addition was complete, the mixture was stirred for 1 h and then filtered. The precipitate was washed first with anhydrous THF (2 x 10 mL) and then with anhydrous DCM (3 x 10 mL) and dried in vacuo to yield 10 g of an off-white solid. 1H-NMR (300 MHz, CD3OD): 10.39 (s, IH), 8.32 (d, 2H), 7.73 (d, 2H), 7.60 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 18 5-Chloro-N-({(5S)-2-oxo-3-[4-(1-pyrrolidinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide The compound 5-chloro-N-({(5S)-2-oxo-3-[4-(1-pyrrolidinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide is obtained from 4-pyrrolidin-1-ylaniline (Reppe et al., Justus Liebigs Ann. Chem.; 596; 1955; 151) in analogy to Example 17. IC50=40 nM; M.p.: 216 C.; Rf (SiO2, toluene/ethyl acetate 1:1)=0.31 [precursor: 0.0]. | ||
Example 18 5-Chloro-N-({(5S)-2-oxo-3-[4-(1-pyrrolidinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide The compound 5-chloro-N-({(5S)-2-oxo-3-[4-(1-pyrrolidinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide is obtained from 4-pyrrolidin-1-ylaniline (Reppe et al., Justus Liebigs Ann. Chem.; 596; 1955; 151) in analogy to Example 17. IC50=40 nM; M.p.: 216 C.; Rf (SiO2, toluene/ethyl acetate 1:1)=0.31 [precursor: =0.0]. | ||
Example 18 5-Chloro-N-({(5S)-2-oxo-3-[4-(1-pyrrolidinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide Analogously to Example 17, starting from <strong>[2632-65-7]4-pyrrolidin-1-yl-aniline</strong> (Reppe et al., Justus Liebigs Ann. Chem.; 596; 1955; 151) the compound 5-chloro-N-({(5S)-2-oxo-3-[4-(1-pyrrolidinyl)phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide is obtained. IC50=40 nM; m.p.: 216 C.; Rf value (SiO2, toluene/ethyl acetate 1:1)=0.31 [starting material:=0.0]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In 2-methoxy-ethanol; at 180℃; for 0.666667h;Microwave irradiation; | 7-(3-Chloro-phenyl)-2-methanesulfmyl-pyrrolo[2,l-f][l,2,4]triazine (125.0 mg, 0.0004284 mol), N,N-Diisopropylethylamine (0.112 mL, 0.000643 mol) and 4-Pyrrolidin-l-yl- phenylamine (139 mg, 0.000857 mol) were dissolved in 2-Methoxyethanol (3.01 mL) and The reaction was microwaved on 300 watts , 1800C for 40 minutes or until HPLC showed consumption of starting material. The reaction mixture was then reduced en vacuo and the product was isolated and purified by Gilson prep HPLC to afford 26.91 mg of [7-(3- Chloro-phenyl)-pyrrolo[2, 1 -fj [ 1 ,2,4]triazin-2-yl]-(4-pyrrolidin- 1 -yl-phenyl)-amine as a lyophilized powder. (M+H)=390.09. 1H NMR (400 MHz, CDCl3) delta 9.63 (s, IH), 8.63 (s, IH), 8.32 (s, IH), 7.84 (m, IH), 7.76 (d, 2H, J = 8.93 Hz), 7.48 (m, 2H), 7.34 (d, 2H, J = 8.93 Hz), 7.21 (m, IH), 7.18 (m, IH), 3.66 (m, 4H), 2.25 (m, 4H). |
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Bis(4-dimethylaminophenyl)amine
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