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Chemical Structure| 852180-47-3 Chemical Structure| 852180-47-3

Structure of 852180-47-3

Chemical Structure| 852180-47-3

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Product Details of [ 852180-47-3 ]

CAS No. :852180-47-3
Formula : C16H25N3O2
M.W : 291.39
SMILES Code : CC(C)(C)OC(=O)N1CCN(CC1)C1=CC=C(CN)C=C1
MDL No. :MFCD03791213
InChI Key :TTXMFUXVXBAVIP-UHFFFAOYSA-N
Pubchem ID :2763841

Safety of [ 852180-47-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301
Precautionary Statements:P301+P310
Class:6.1
UN#:2811
Packing Group:

Application In Synthesis of [ 852180-47-3 ]

* 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 [ 852180-47-3 ]

[ 852180-47-3 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 852180-47-3 ]
  • [ 25084-14-4 ]
  • [ 831203-79-3 ]
  • 2
  • [ 186650-98-6 ]
  • [ 852180-47-3 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogen; In methanol; at 20℃; under 2327.23 Torr; for 4h; To a solution of G1 (1.00 g, 3.50 mmol) in MeOH (50 mL) was added Raney-Ni (0.50 g). The suspension was degassed under vacuum and purged with H2 for three times. The reaction mixture was stirred at 20 C for 4 hours under H2 atmosphere (45 psi). LCMS showed the reaction was completed. The reaction mixture was filtrated and the filtrate was concentrated under reduced pressure and purified by silica gel column (eluent: EtOAc/PE = 3/1 to EtOAc, 1% TEA as additive) to afford 1.00 g (yield: 100%) of compound G2 as a white powder.
99% With ammonia; hydrogen; In methanol; at 20℃; for 16h; Under hydrogen, N-Boc-4- (4-cyanophenyl) piperazine (1 g, 3.48 mmol), ammonia (1 mL) and Raney nickel (50 mg) were added to methanol (10 mL). The reaction system was at room temperature. Stir for 16 hours.Filtration and concentration of the filtrate to dryness gave 1-N-Boc-4- (4- (aminomethyl) phenyl) piperazine (9A, 1 g, yield: 99%) as a white solid.
With hydrogen; In methanol; To a stirred solution of 14f (1.55mmol) in methanol (10mL) was added a portion of Raney-Ni and the mixture was stirred for 4h under H2 atmosphere. The reaction mixture was filtered by cellite and the filtrate was concentrated. The crude residue was purified by flash column chromatography (methylene chloride:MeOH=20:1) to give 23.
  • 3
  • [ 852180-47-3 ]
  • [ 831203-80-6 ]
  • 4
  • [ 852180-47-3 ]
  • 4-(4-[(5-nitro-furan-2-carbonyl)-amino]-methyl}-phenyl)-piperazine-1-carboxylic acid methyl ester [ No CAS ]
  • 5
  • [ 852180-47-3 ]
  • 4-(4-[(5-nitro-furan-2-carbonyl)-amino]-methyl}-phenyl)-piperazine-1-carboxylic acid ethyl ester [ No CAS ]
  • 6
  • [ 852180-47-3 ]
  • 4-(4-[(5-nitro-furan-2-carbonyl)-amino]-methyl}-phenyl)-piperazine-1-carboxylic acid allyl ester [ No CAS ]
  • 7
  • [ 852180-47-3 ]
  • 4-(4-[(5-nitro-furan-2-carbonyl)-amino]-methyl}-phenyl)-piperazine-1-carboxylic acid isobutyl ester [ No CAS ]
  • 8
  • [ 852180-47-3 ]
  • 4-(4-[(5-nitro-furan-2-carbonyl)-amino]-methyl}-phenyl)-piperazine-1-carboxylic acid isopropylamide [ No CAS ]
  • 9
  • [ 852180-47-3 ]
  • 4-(4-[(5-nitro-furan-2-carbonyl)-amino]-methyl}-phenyl)-piperazine-1-carboxylic acid propylamide [ No CAS ]
  • 10
  • [ 852180-47-3 ]
  • 4-(4-[(5-nitro-furan-2-carbonyl)-amino]-methyl}-phenyl)-piperazine-1-carboxylic acid butyl ester [ No CAS ]
  • 13
  • [ 852180-47-3 ]
  • [ 1038388-17-8 ]
  • [ 1038388-18-9 ]
YieldReaction ConditionsOperation in experiment
Example 2CPart A:2- Thiphene-3-yl-imidazo[1 ,2-a]pyridine-3,8-dicarboxylic acid 163 (0.05 mmol) dissolved in in dichloromethane (5 ml_) and cooled to -200C. To this (1-(3- dimethylaminopropyl)-3-ethylcarbodiimide (1.2 equivalents, 0.06 mmol) was added. Followed by Diisopropyl ethyl amine (3 equivalents) was added and the solution stirred at - 200C for 15 minutes. To the activated acid was added with 0.05 mmol solution of Amine (pre dissolved in to DCM or NMP; 0.5 ml_). The solution was shaken <n="116"/>at -50C for 14 hrs. LCMS analysis showed the completion of the reaction. HPLC-LC- MS mass calculated for formula C3IH35N5O5S, 589.23; and observe m/z M++H 590.0
Example 2CPart A:2- Thiphene-3-yl-imidazo[1 ,2-a]pyridine-3,8-dicarboxylic acid 163 (0.05 mmol) dissolved in in dichloromethane (5 ml_) and cooled to -200C. To this (1-(3- dimethylaminopropyl)-3-ethylcarbodiimide (1.2 equivalents, 0.06 mmol) was added. Followed by Diisopropyl ethyl amine (3 equivalents) was added and the solution stirred at - 200C for 15 minutes. To the activated acid was added with 0.05 mmol solution of Amine (pre dissolved in to DCM or NMP; 0.5 ml_). The solution was shaken <n="116"/>at -50C for 14 hrs. LCMS analysis showed the completion of the reaction. HPLC-LC- MS mass calculated for formula C3IH35N5O5S, 589.23; and observe m/z M++H 590.0
  • 14
  • [ 852180-47-3 ]
  • [ 1149380-77-7 ]
  • [ 1149380-80-2 ]
YieldReaction ConditionsOperation in experiment
97% With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 24h; STEP 5: A solution of tert-butyl 4-[4-(aminomethyl)phenyl]piperazine-l- carboxylate (223 mg, 0.77 mmol), 6-[3-endo-([2-methyl-3-methyloxy)phenyl]- carbonyl}amino)-8-azabicyclo[3.2.1]oct-8-yl]pvridine-3-carboxylic acid (324 mg, 0.77 mmol), HATU (291 mg, 0.77 mmol), and diisopropylethylamine (302 mg, 2.34 mmol) in dimethylformamide (5 mL) was stirred at room temperature for 24 hours. The reaction mixture was diluted with ethyl acetate (50 mL), washed with saturated sodium bicarbonate (25 mL), 5% aqueous lithium chloride (2 x 25 mL), and brine (25 mL), dried over sodium sulfate, and dried to provide 1 ,1-dimethylethyl 4-(4-[({6-[3- endo-([2-methyl-3-(methyloxy)phenyl]carbonyl}amino)-8-azabicyclo[3.2.1]oct-8- yl]pyridine-3-yl}carbonyl)amino]methyl}phenyl)piperazine-l-carboxylate (498 mg, 97% yield). 1H NMR (400 MHz, CDCl3): 8.58 (d, IH), 7.90 (dd, IH), 7.28 (m, IH), <n="201"/>7.21 (t, IH), 6.92 (m, 4H), 6.53 (d, IH), 6.19 (d, I H), 6.13 (t, I H), 4.61 (br s, 2H), 4.55 (d, 2H), 4.25 (m, IH), 3.85 (s, 3H), 3.57 (m, 4H), 3.12 (m, 4H), 2.34 (m, 2H), 2.29 (s, 3H), 2.21 (m, 2H), 2.00 (m, 2H), 1.82 (d, 2H), 1.48 (s, 9H); MS (EI) for C38H48N6O5: 669 (MH+).
  • 15
  • [ 852180-47-3 ]
  • [ 1033693-56-9 ]
  • [ 1033693-69-4 ]
YieldReaction ConditionsOperation in experiment
83% With triethylamine; In tetrahydrofuran; at 20℃; for 48h; EXAMPLE E1; 1-[4-(4-ethylpiperazin-1-yl)benzyl]-3-isobutylimidazo[2,1-b]quinazoline-2,5(1H,3H)-dione hydrochloride Stage 1: tert-butyl 4-{4-[(3-isobutyl-2,5-dioxo-2,3-dihydroimidazo[2,1-b]quinazolin-1(5H)-yl)methyl]phenyl}piperazine-1-carboxylateTert-butyl 4-[4-(aminomethyl)phenyl]piperazine-1-carboxylate (930 mg) and triethylamine (0.56 mL) are added to a solution of methyl 1-(2-chloro-4-oxoquinazolin-3(4H)-yl)cyclopentane carboxylate (prepared according to Example A2; 620 mg) in THF (5 mL). The mixture is stirred for 48 hours at ambient temperature then the precipitate formed is filtered and washed with THF. The filtrate is concentrated under reduced pressure at 40 C. then purified by flash chromatography on silica gel (eluent: 100% heptane to heptane/ethyl acetate 7:3) produces the expected compound in the form of white powder (880 mg, 83% yield).MS/LC: calculated MM=531.3; m/z=532.3 (MH+)NMR (1H, 400 MHz, DMSO-d6): δ0.80 (m, 6H), 1.40 (s, 9H), 1.79 (m, 1H), 2.01 (m, 2H), 3.05 (t, 4H), 3.41 (t, 4H), 4.77 (AB, 1H), 4.82 (AB, 1H), 4.93 (t, 1H), 6.90 (AB, 2H), 7.30 (AB, 2H), 7.41 (t, 1H), 7.57 (AB, 1H), 7.77 (t, 1H), 8.08 (AB, 1H).
  • 16
  • [ 852180-47-3 ]
  • [ 1349744-81-5 ]
  • [ 1349745-15-8 ]
YieldReaction ConditionsOperation in experiment
65% With hydroquinone; In isopropyl alcohol; at 100℃; for 30h; A stirred solution of 4-(4-aminomethyl-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.531 g, 1.82 mmol), 1-chloro-4-methoxy-5-nitro-2-vinylbenzene (Example 50C) (0.3 g, 1.40 mmol) and quinol (61.8 mg, 0.562 mmol) in isopropyl alcohol (16 mL) was heated to 100C for 30 hours. The mixture was allowed to cool to room temperature and concentrated under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 2% methanol in DCM to give the title compound (0.460 g, 65%)
  • 17
  • [ 852180-47-3 ]
  • [ 1216142-18-5 ]
  • C26H32ClN5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; at 20℃; for 16h; A mixture of compound 6-chloro-2-ethylimidazo[1,2-a]pyridine-3-carboxylic acid (140 mg, 0.48 mmol), G2 (90 mg, 0.40 mmol), EDCI (234 mg, 1.20 mmol), HOBt (162 mg, 1.20 mmol) and TEA (121 mg, 2.00 mmol) in THF (10 mL) was stirred at 20 C for 16 hours. LCMS showed the reaction was finished. The reaction mixture was poured into water (30 mL), extracted with EtOAc (20 mL X 3). The combined extracts were washed with brine (10 mL), dried over anliydrous Na2SO4 and concentrated to give a residue. The residue was purified by silica gel column (eluent: PE/EtOAc = 8/1 to 4/1) to afford 120 mg (yield: 47%) of compound G3 as a white powder.
  • 18
  • [ 852180-47-3 ]
  • C21H24ClN5O*C2HF3O2 [ No CAS ]
  • 19
  • [ 852180-47-3 ]
  • [ 1403940-97-5 ]
  • 20
  • [ 852180-47-3 ]
  • 3-{(3R)-3-[(6-chloro-5-fluoro-2-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-4-yl)amino]piperidin-1-yl}-3-oxopropanenitrile [ No CAS ]
  • (R)-tert-butyl 4-(4-(((6-((1-(2-cyanoacetyl)piperidin-3-yl)amino)-5-fluoro-2-(pyrazolo[1,5-a]pyridin-3-yl)pyrimidin-4-yl)amino)methyl)phenyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% In 1-methyl-pyrrolidin-2-one; at 140℃; for 2h;Microwave irradiation; A microwave reactor was charged with 3-{(3R)-3-[(6-chloro-5-fluoro-2-pyrazolo[1 ,5-a] pyridin-3-ylpyrimidin-4-yl)amino]piperidin-1 -yl}-3-oxopropanenitrile (Preparation 6c, 0.15 g, 0.36 mmol) and tert-butyl 4-[4-(aminomethyl)phenyl]piperazine-1 -carboxylate (0.42 g, 1.45 mmol) in N-methylpyrrolidone (1.5 mL). The reaction mixture was subjected to microwave irradiation for 2 hours at 140 C then poured into water. Theprecipitate was filtered, washed with water, dried and purified by flash chromatography (dichloromethane to dichloromethane/methanol 95:5) to yield the title compound (77 mg, 32%).LRMS (mlz): 669 (M+1).
  • 21
  • [ 1194-02-1 ]
  • [ 57260-71-6 ]
  • [ 852180-47-3 ]
  • 22
  • [ 623-00-7 ]
  • [ 57260-71-6 ]
  • [ 852180-47-3 ]
  • 23
  • [ 852180-47-3 ]
  • [(2R,6R)-4-(7-cyanopyrazolo[1,5-a]pyridin-4-yl)-6-methylmorpholin-2-yl]methyl trifluoromethanesulfonate [ No CAS ]
  • tert-butyl 4-[4-[[[(2S,6R)-4-(7-cyanopyrazolo[1,5-a]pyridin-4-yl)-6-methyl-morpholin-2-yl]methylamino]methyl]phenyl]piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
52 mg With potassium carbonate; In acetonitrile; for 3h;Reflux; Step 1: preparation of tert-butyl 4-[4-[[[(2S,6R)-4-(7-cyanopyrazolo[1,5-a]pyridin-4-yl)-6-methyl-morpholin-2-yl]methylamino]methyl]phenyl]piperazine-1-carboxylate (compound 16a) To a solution of ((2R,6R)-4-(7-cyanopyrazolo[1,5-a]pyridin-4-yl)-6-methylmorpholin-2-yl)methyl trifluoromethanesulfonate (Intermediate A, 40 mg, 99 μmol) in ACN (4 mL) was added <strong>[852180-47-3]tert-butyl 4-(4-(aminomethyl)phenyl)piperazine-1-carboxylate</strong> (43 mg, 0.15 mmol) and K2CO3 (41 mg, 0.30 mmol). The reaction mixture was refluxed for 3h, then cooled to rt, diluted with ACN (10 mL), and filtered through celite, the filtrate was concentrated to give a yellow solid which was purified by column chromatography to give compound 16a (52 mg) as a yellow solid. MS: calc'd 546 (MH+), measured 546 (MH+).
  • 24
  • [ 852180-47-3 ]
  • 5-((4R,9aS)-4-methyl-8-oxooctahydro-2H-pyrido[1,2-a]pyrazin-2-yl)quinoline-8-carbonitrile [ No CAS ]
  • tert-butyl 4-(4-((((4R,9aS)-2-(8-cyanoquinolin-5-yl)-4-methyloctahydro-2H-pyrido[1,2-a]pyrazin-8-yl)amino)methyl)phenyl)piperazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
50 mg A solution of 5-((4R,9aS)-4-methyl-8-oxooctahydro-2H-pyrido[1,2-a]pyrazin-2- yl)quinoline-8-carbonitrile (Intermediate C1, 32 mg, 99.9 µmol), tert-butyl 4-(4- (aminomethyl)phenyl)piperazine-1-carboxylate (Compound 1a, CAS: 852180-47-3, Vendor: Accela ChemBio Inc, 29 mg, 99.9 µmol) in MeOH (4 mL) was stirred at room temperature for 1 hour. Then the reaction mixture was cooled at 0C and sodium cyanotrihydroborate (12 mg, 200 µmol) was added. The reaction mixture was stirred at room temperature for 12 hrs. The mixture was quenched with water (10 mL), extracted with EA twice. The combined organic layer was washed with brine, dried over Na2SO4, filtered and concentrated to afford crude tert-butyl 4-(4- ((((4R,9aS)-2-(8-cyanoquinolin-5-yl)-4-methyloctahydro-2H-pyrido[1,2-a]pyrazin-8- yl)amino)methyl)phenyl)piperazine-1-carboxylate (Compound 1b, 50 mg) which was used for next step without purification. MS: calc’d 596 (MH+), measured 596 (MH+).
  • 25
  • [ 852180-47-3 ]
  • 5-((4R,9aS)-4-methyl-8-oxooctahydro-2H-pyrido[1,2-a]pyrazin-2-yl)quinoline-8-carbonitrile [ No CAS ]
  • 5-[(4R,8R,9aS)-4-methyl-8-[(4-piperazin-1-ylphenyl)methylamino]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]quinoline-8-carbonitrile [ No CAS ]
  • 5-[(4R,8S,9aS)-4-methyl-8-[(4-piperazin-1-ylphenyl)methylamino]-1,3,4,6,7,8,9,9a-octahydropyrido[1,2-a]pyrazin-2-yl]quinoline-8-carbonitrile [ No CAS ]
 

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