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[ CAS No. 1151665-15-4 ] {[proInfo.proName]}

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Chemical Structure| 1151665-15-4
Chemical Structure| 1151665-15-4
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Product Details of [ 1151665-15-4 ]

CAS No. :1151665-15-4 MDL No. :MFCD10565958
Formula : C13H17ClN2O2 Boiling Point : No data available
Linear Structure Formula :- InChI Key :-
M.W : 268.74 Pubchem ID :-
Synonyms :

Safety of [ 1151665-15-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1151665-15-4 ]

* 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 [ 1151665-15-4 ]

[ 1151665-15-4 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 766545-20-4 ]
  • [ 24424-99-5 ]
  • [ 1151665-15-4 ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 2h; To a slurry of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (106.1 g, 517 mmol, commercially available from D-L Chiral Chemicals, ST-0143) and N,N-diisopropylethylamine (80 g, 108 mL, 621 mmol, 1.2 eq) in DCM (1 L) was added a solution of di-tert-butyl dicarbonate (119 g, 543 mmol, 1.05 eq) in DCM (100 mL) via an addition funnel within 1 hr. The reaction mixture became a clean solution and the solution thus obtained was stirred at room temperature for an additional hour and monitored using LCMS. Upon completion, the reaction mixture was concentrated. The residue was dissolved in EtOAc (1 L) and washed with water (3*300 mL), washed with brine (300 mL) and dried over Mg504. The solvent was evaporated under vacuum to give the title compound as an off-white solid (139 g, yield: 100%). 1H NMR (400 MHz, CDCl3) delta ppm 1.49 (9H, s), 2.97 (2H, t, J=5.9 Hz), 3.73 (2H, t, J=6.0 Hz), 4.57 (2H, s), 7.17 (1H, d, J=8.0 Hz), 7.38 (1H, d, J=8.0 Hz) ppm; LCMS m/z: 269 (M+1).
95.41% With triethylamine; In dichloromethane; at 15℃; for 12h;Inert atmosphere; 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine hydrochloride (2.00 g, 9.75 mmol, 1.00 eq) was dissolved in DCM (20.00 mL) and triethylamine (2.47 g, 24.38 mmol, 2.50 eq) and di-tert-butyl dicarbonate (3.19 g, 14.63 mmol, 1.50 eq) were added at 15 C under the nitrogen gas atmosphere. The mixture was stirred at 15 C for 12 hours. The mixture was poured into water (30 mL) and the aqueous phase was extracted with dichloromethane (100 mL * 4). The combined organic phases were washed with saturated brine (100 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to deliver tert-butyl 2-chloro-7,8-dihydro-5H-1,6-naphthyridine-6-carboxylate (2.50 g, 9.30 mmol, 95.41% yield) as a white solid. LCMS (ESI) m / z: 269 (M + 1).
92% To a solution of compound 36 (5 g, 24.4 mmol, 1 eq) in DCM (40 mL) was added DIEA (9.45 g, 73.1 mmol, 3 eq) and stirred for 20 mins, B0C2O (6.5 g, 29.3 mmol, 1.2 eq) in DCM (30 mL) was added drop wise and then stirred for lh. After LCMS and TLC indicated completion, the mixture was concentrated and the residue was dissolved in EA (200 mL), washed with water (100 mL X 3) and brine (100 mL), dried over sodium sulfate, concentrated and purified by silica column to give the desired product as white solid (6 g, 92%). *H NMR (300 MHz, CDCb-de): delta 7.39 (d, J= 8.1 Hz, 1 H), 7.18 (d, J= 8.1 Hz, 1 H), 4.57 (s, 2 H), 3.74 (t, J= 6.0 Hz, 2 H), 2.98 (t, J= 5.4 Hz 2 H), 1.53 (s, 9 H). LCMS: (M+H)+: 268.9.
89% With triethylamine;dmap; In dichloromethane; at 0 - 20℃; Di-tert-butyl dicarbonate (2.40 g, 11 mmol) was added to a solution of 2-chloro-5,6,7,8- tetrahydro-l,6-naphthyridine hydrochloride (available from Activate Scientific) (2.05 g, 10 mmol) and Et3N (3.33 g, 4.59 mL, 33 mmol) in DCM at 00C. DMAP (0.12 g, 1.00 mmol) was added and the reaction was stirred at RT for 3 days. The reaction was diluted with DCM and washed successively with 10% w/v citric acid (aq.), saturated NaHCO3 (aq.), water, dried (Na2SO4), filtered and concentrated at reduced pressure. The residue (2.8g) was purified by FCC (SiO2, eluting with 9:1 to 3:1 heptane / EtOAc) to give the title compound (2.63 g, 89%). LCMS data: Calculated MH+ (269); Found 100% (MH+) m/z 269, Rt = 1.33 min. 1H NMR (250 MHz, CHLOROFORM-J) delta ppm 1.49 (8 H, s) 2.97 (2 H, t, J=5.86 Hz) 3.73 (2 H, t, J=5.94 Hz) 4.57 (2 H, s) 7.17 (1 H, d, J=8.07 Hz) 7.38 (1 H, d, J=8.07 Hz).
With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere; To a solution of 2-chloro-5,6,7,8-tetrahydro-[l,6]naphthyridine hydrochloride (1.54 g, 7.5 mmol) in DCM (25 mL) was added EtsN (2 mL, 15 mmol). After the addition and stirring - 139 -at room temperature for 5 min, the solution was cooled to 0 C, followed by the addition of (Boc)20 (1.88 g, 8.63 mmol). The resulting reaction mixture was then allowed to stir at room temperature for 2 hours. It was then washed with H20 and brine. The organic layer was dried over anhy. Na2S04, filtered and concentrated in vacuo to give the title compound (1.87 g, 93%) as a white solid. MS: 269.1 (M+H+). It was used directly in the next step without further purification.

  • 2
  • [ 869224-62-4 ]
  • [ 1151665-15-4 ]
  • [ 1190440-42-6 ]
YieldReaction ConditionsOperation in experiment
55% With potassium tert-butylate; In 1,4-dioxane; at 115℃; for 0.666667h;Inert atmosphere; Microwave irradiation; A mixture of tert-butyl 2-chloro-7,8-dihydro-l,6-naphthyridine-6(5H)-carboxylate ( 0.59 g, 2.20 mmol), l-cyclobutylpiperidin-4-ol (0.52 g, 3.30 mmol) and potassium tert-butoxide (0.62 g, 5.50 mmol) in dioxane (20 volumes) was heated at 115C for 40 min in a CEM microwave reactor (150W) under N2 (g) atmosphere. The reaction mixture was diluted with EtOAc, <n="80"/>washed with brine, dried (Na2SO4), filtered and concentrated at reduced pressure. The residue (0.9 g) was purified by FCC (SiO2, eluting with DCM/MeOH/NH3, 90:10:1) to give the title compound (0.47 g, 55%).LCMS data: Calculated MH+ (387); Found 100% (M+) m/z 387, Rt = 5.78 min. 1H NMR (250 MHz, CHLOROFORM-J) delta ppm 1.38 - 2.15 (21 H, m) 2.47 - 2.81 (5 H, m) 3.63 (2 H, t, J=5.86 Hz) 4.40 (2 H, s) 4.97 (1 H, br. s.) 6.47 (1 H, d, J=8.38 Hz) 7.06 (1 H, d, J=8.38 Hz).
  • 3
  • [ 55552-70-0 ]
  • [ 1151665-15-4 ]
  • [ 1151665-16-5 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.333333h;Inert atmosphere; Microwave irradiation; (step 2) To a mixed solution of the compound (0.300 g) obtained in step 1, 3-furylboronic acid (0.187 g) and potassium carbonate (0.154 g) in DME/water (6 mL)/0.6 mL) was added under an argon atmosphere tetrakis(triphenylphosphine)palladium (0) (Pd(PPh3)4) (0.129 g), and the reaction vessel was irradiated in a microwave reaction apparatus at 150C for 20 min. To the reaction solution was added water, and the resulting product was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (solvent gradient: 0?30% ethyl acetate/hexane) to give tert-butyl 2-(3-furyl)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (0.310 g, 92%) as an oil. 1H-NMR(CDCl3):delta1.50(9H,s), 2.95-3.05(2H,m), 3.73-3.77(2H,m), 4.58(2H,s), 6.87(1H,dd,J=1.7Hz,0.7Hz), 7.29(1H,d,J=8.2Hz), 7.39(1H,d,J=8.2Hz), 7.47(1H,dd,J=1.7Hz,1.7Hz), 7.99(1H,s)
  • 4
  • [ 210539-04-1 ]
  • [ 24424-99-5 ]
  • [ 1151665-15-4 ]
YieldReaction ConditionsOperation in experiment
75% Example 26 2-(3-Furyl)-5,6,7,8-tetrahydro-1,6-naphthyridine dihydrochloride (step 1) To a solution of the compound (2.00 g) obtained in Example 6, step 2 in dichloroethane (30 mL) was added 1-chloroethyl chloroformate (0.917 mL), and the mixture was stirred at 90C for 2 hr. The reaction mixture was cooled to room temperature, and concentrated. To the obtained residue was added methanol (20 mL), and the mixture was stirred under reflux for 1 hr. To the reaction mixture was added diisopropyl ether (30 mL), and the precipitate was collected by filtration. A mixed solution of the obtained solid (1.55 g) and (Boc)2O (1.69 g) in THF/1N aqueous sodium hydroxide solution (23 mL/23 mL) was stirred at room temperature for 16 hr. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give tert-butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate (1.56 g, 75%) as a white powder. 1H-NMR(CDCl3):delta1.49(9H,s), 2.97(2H,t,J=6.0Hz), 3.73(2H,d,J=6.0Hz), 4.56(2H,s), 7.17(1H,d,J=8.2Hz), 7.38(1H,d,J=8.2Hz)
  • 5
  • [ 1013-88-3 ]
  • [ 1151665-15-4 ]
  • [ 1346673-94-6 ]
YieldReaction ConditionsOperation in experiment
33% 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 110℃; for 3.08333h;Inert atmosphere; Nitrogen was bubbled into a solution of compound 37 (1.0 g, 3.7 mmol, 1.0 eq), compound 38 (742 mg, 4.1 mmol, 1.1 eq), Pd2(dba)3 (340 mg, 0.37 mmol, 0.1 eq), Xantphos (454 mg, 0.78 mmol, 0.21 eq) and CS2CO3 (2.4 g, 7.4 mmol, 2 eq) in dioxane (20 mL) for 5 mins. The mixture was stirred at 110 C for 3 h. After completion, the mixture was cooled down to RT, diluted with DCM (50 mL) and filtered through a pad of Celite, rinsed with DCM (20 mL). The filtrate was dried over sodium sulfate, concentrated and purified by silica column to give the desired product as a yellow solid (0.5 g, 33%). NMR (300 MHz, CDCb): delta 7.36-7.25 (m, 10 H), 7.17 (d, J= 8.1 Hz, 1 H), 6.35 (d, J= 8.4 Hz, 1 H), 4.48 (s, 2 H), 3.70 (t, J= 6.0 Hz, 2 H), 2.92 (s, J= 6.0 Hz, 2 H), 1.50 (s, 9 H). LCMS: (M+H)+:413.9.
With caesium carbonate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 110℃; for 48h; To a round-bottomed flask equipped with a stirring bar, tert-butyl 2-chloro-7,8- dihydro-l,6-naphthyridine-6(5H)-carboxylate (1.09 g, 4.05 mmol), diphenyl-methanimine 26 (2.20 g, 12.14 mmol), Pd(OAc)2 (181.6 mg, 0.809 mmol), BINAP (503.8 mg, 0.809 mmol), CS2CO3 (6.59 g, 20.23 mmol) and toluene (16 mL) were added. The reaction mixture was heated at 110 C for 2 days. The reaction mixture was filtered and removed solvent in vacuo. The residue 158a was directly used in the next step.
With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; Intermediate W-1 was synthesized through the reaction of <strong>[1151665-15-4]tert-butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate</strong> with benzophenone imine and tert-butoxysodium in the presence of a Pd catalyst and deprotection.
  • 7
  • [ 1151665-15-4 ]
  • [ 1346673-95-7 ]
  • 8
  • [ 1151665-15-4 ]
  • [ 1346673-96-8 ]
  • 9
  • [ 1151665-15-4 ]
  • [ 1346670-07-2 ]
  • 10
  • 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine [ No CAS ]
  • [ 24424-99-5 ]
  • [ 1151665-15-4 ]
YieldReaction ConditionsOperation in experiment
97% With triethylamine; In dichloromethane; at 20℃; for 1h;Cooling with ice; 1) In a 250mL single-mouth bottle,will2-chloro-5,6,7,8-tetrahydronaphthyridine 20.0g and 14.0gTriethylamine was dissolved in 50 mL of dichloromethane.The solution was stirred and cooled in an ice salt bath.27.2g Boc2O was added dropwise,After the addition was completed, the reaction was carried out at room temperature for 1 h.Dilute with 50 mL of dichloromethane.Wash twice with 1 mol/L of dilute hydrochloric acid,Wash once with saturated sodium bicarbonate and once with saturated brine.The organic phase was dried over anhydrous magnesium sulfate.filter,The filtrate was spun dry to give 30.9 g of a pale yellow color.which is2-chloro-6-tert-butoxycarbonyl-5,7,8-trihydro-1,6-naphthyridine, yield 97%,
89.75% With sodium hydrogencarbonate; In dichloromethane; water; at 15℃; for 2h; 2-Chloro-5,6,7,8-tetrahydro-1,6-naphthyridine (850.00 mg, 4.14 mmol, 1.00 eq) and Di-tert-butyl dicarbonate (1.36 g, 6.22 mmol, 1.50 eq) were dissolved in a mixed solution of dichloromethane (15.00 mL) and water (15.00 mL), sodium bicarbonate (1.04 g, 12.43 mmol, 3.00 eq) was added at 15 C. The mixture was stirred at 15 C for 2 hours. The mixture was poured into water (30 mL) and the aqueous phase was extracted with ethyl acetate (50 mL * 3). The combined organic phases were washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (petroleum ether / ethyl acetate = 50/1, 30/1) to deliver tert-butyl-2-chloro-7,8-dihydro-1,6-naphthyridin-6(5H)-carboxylate (1.00 g, 3.72 mmol, 89.75% yield) as a white solid.
87% Example 22-Oxo-3-(5,6,7,8-tetrahydro-1,6-naphthyridin-2-yl)indoline-5-carbonitrile2.1 tert-Butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylateTo a solution of 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine (500 mg, 2.97 mmol) in dioxane (7.4 mL) and water (7.4 mL) was added sodium bicarbonate in as a solid in one portion (498 mg, 5.93 mmol). After stirring the resulting suspension for 10 min at RT Boc2O (777 mg, 3.56 mmol) was added and the mixture was stirred for 16 h. The mixture was diluted with ethyl acetate and the organic layer was washed with water and brine. The organic phase was dried over sodium sulfate, filtered, and evaporated to dryness. Amount 693 mg. Yield 87%.1H-NMR (CDCl3, 400 MHz) delta 1.52 (s, 9H), 2.99 (t, 2H), 3.75 (t, 2H), 4.58 (s, 2H), 7.17 (d, 1H), 7.39 (d, 1H)MS (ES-API) m/z 369.1 (M+H+, 100%).
85.44% With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 3.16667h; In a 100mL one-neck flask, 2-chloro-5,6,7,8-tetrahydro-1,6-naphthyridine (170mg, 1.0mmol) (25mL) was dissolved in tetrahydrofuran,At 0 was added triethylamine (0.35mL, 2.5mmol), (Boc) 2O (240mg, 1.1mmol), stirred for 10min, then the reaction mixture was slowly raised toRoom temperature for 3h.The solvent was distilled off under reduced pressure, to the residue was added methylene chloride (100 mL) and water (100 mL), the organic layer was washed with saturated brineWash (80mL × 3), the organic layer was dried over anhydrous sodium sulfate and concentrated.The crude product was purified by column chromatography (petroleum ether / ethyl acetate(V / V) = 5/1), a pale yellow solid (229mg, 85.44%).

  • 11
  • [ 1151665-15-4 ]
  • [ 1401034-54-5 ]
  • 12
  • [ 1151665-15-4 ]
  • [ 1401034-02-3 ]
  • 13
  • [ 1151665-15-4 ]
  • [ 1401034-03-4 ]
  • 14
  • [ 1169698-48-9 ]
  • [ 1151665-15-4 ]
  • [ 1401034-58-9 ]
YieldReaction ConditionsOperation in experiment
72% With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 150℃; for 1h;Microwave radiation; To a solution of 9-cyclopentyl-9H-pyrido[4',3':4,5]pyrrolo[2,3-d]pyrimidin-2-amine (prepared as described in WO 2009/085185) (152 mg, 0.6 mmol) in dioxane (6 mL) were added <strong>[1151665-15-4]tert-butyl 2-chloro-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate</strong> (177 mg, 0.66 mmol), tris(dibenzylideneacetone)dipalladium (0) (28 mg, 0.030 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (52 mg, 0.090 mmol), and sodium t-butoxide (86 mg, 0.9 mmol). The reaction mixture thus obtained was heated at 150 C. under microwave irradiation for 1 hour. The reaction mixture was diluted with DCM, washed with brine, and then dried. The solvent was evaporated and the residue was purified by flash chromatography on silica gel eluting with 10% to 50% solvent A (DCM/MeOH/NH4OH, 100:10:1) in DCM to give the title compound as a light yellow solid (211 mg, 72% yield). 1H NMR (500 MHz, CDCl3) delta 1.52 (9H, s), 1.88-1.90 (2H, m), 2.14-2.21 (4H, m), 2.45-2.47 (2H, m), 2.92-2.94 (2H, m), 3.76-3.79 (2H, m), 4.59 (2H, m), 5.37 (1H, m), 7.49 (1H, d, J=10.0 Hz), 7.85 (1H, d, J=5.0 Hz), 8.14 (1H, br. s), 8.37 (1H, d, J=10.0 Hz), 8.52 (1H, d, J=5.0 Hz), 8.92 (1H, s), 9.11 (1H, s) ppm; LCMS m/z: 486 (M+1).
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