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[ CAS No. 20426-80-6 ] {[proInfo.proName]}

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Product Details of [ 20426-80-6 ]

CAS No. :20426-80-6 MDL No. :MFCD11848749
Formula : C10H10O3 Boiling Point : -
Linear Structure Formula :- InChI Key :RGWHTTALQBHDGZ-UHFFFAOYSA-N
M.W : 178.18 Pubchem ID :188669
Synonyms :

Safety of [ 20426-80-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501 UN#:N/A
Hazard Statements:H302-H312-H332 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 20426-80-6 ]

* 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 [ 20426-80-6 ]

[ 20426-80-6 ] Synthesis Path-Downstream   1~54

  • 1
  • [ 20426-80-6 ]
  • [ 64-17-5 ]
  • [ 112605-35-3 ]
  • 2
  • [ 491-37-2 ]
  • [ 7677-24-9 ]
  • [ 20426-80-6 ]
  • 3
  • [ 113967-29-6 ]
  • [ 20426-80-6 ]
YieldReaction ConditionsOperation in experiment
93.4% With lithium hydroxide; d) (R,S)-Chroman-4-carboxylic acid (80d) Compound 80c (1.21 g, 6.3 mmol) was hydrolyzed with lithium hydroxide (1.35 g, 32 mmol) to give the title acid (1.05 g, 93.4%). 1H NMR (300 MHz, CDCl3) δ: 12.66 (s, 1H), 7.20-7.13 (m, 2H), 6.87-6.78 (m, 2H), 4.18 (m, 2H), 3.75 (t, 1H), 2.16-2.03 (m, 2H).
  • 4
  • [ 74187-63-6 ]
  • [ 20426-80-6 ]
YieldReaction ConditionsOperation in experiment
87% With hydrogenchloride; water; acetic acid; tin(ll) chloride; at 140℃; for 20h; 4-(Trimethylsilyloxy)chroman-4-carbonitrile (7.2 g, 0.029 moles) and tin (II) chloride (23.6 g, 0.125 moles) were dissolved in glacial AcOH (30 mL) and con. HCl (30 mL). The resultant mixture was heated at 140 0C for 20 hours and then cooled to room temp. Diluted the mixture with water (150 mL), extracted with CH2Cl2 (3 x 150 mL), washed the combined extracts with brine and dried (MgSO4). The dried extract was filtered and concentrated under vacuo to afford the title compound as off-white solid (4.45 g. 87% yield). 1H NMR (400 MHz, CDCl3) 7.26 (IH, m), 7.16 (IH, m), 6.84 (IH, m), 4.25 (2H, m), 3.81 (IH, m), 2.32 (IH, m), 2.13 (IH, m).
37% With hydrogenchloride; tin(II) chloride dihdyrate; acetic acid; In water; at 115℃; for 72h;Inert atmosphere; Into a 100-mL round-bottom flask, was placed 4-[(trimethylsilyl)oxy]-3,4-dihydro-2H-l- benzopyran-4-carbonitrile (1.5 g, 6.06 mmol, 1.00 equiv), SnCl2.2H20 (5.5 g, 24.37 mmol, 4.00 equiv), AcOH (10 mL), con. HC1 (10 mL). The resulting solution was stirred for 3 days at 115 C. The resulting solution was cooled to 18 C and diluted with water (50 mL). The resulting solution was extracted with ethyl acetate (100 mL x 2). The organic layers combined, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1/2). The collected fraction was concentrated to give 400 mg (37%) of chroman-4- carboxylic acid as a yellow solid. MS (ES, m/z) [M+H]+: 179.
3.18 g With hydrogenchloride; acetic acid; tin(ll) chloride; for 40h;Reflux; A mixture of Example 29A (4.75 g, 19.2 mmol) and SnCh (10.92 g, 57.6 mmol) in HC1 (37%), 20 mL) and AcOH (20 mL) was heated at reflux for 40 h. The residue was concentrated to remove AcOH and then partitioned between CH2C12 and brine. The organic layer was further washed with brine, dried (Na2S04) and concentrated. Chromatography (Si02, 0 - 40% ethyl acetate in hexane) gave the target compound (3.18 g, 93%) as a white solid.
1.2 g With hydrogenchloride; tin(II) chloride dihdyrate; acetic acid; In water; at 80℃; for 24h; B. To a solution of 4-((trimethylsilyl)oxy)chroman-4-carbonitrile (1.9 g, 7.68 mmol) in HCl (5.0 mL) and AcOH (5.0 mL) was added SnCl2.(H2O)2 (4.32 g, 19.2 mmol). The reaction was stirred at 80 C for 24 h. water (40 mL) was added to the reaction vessel the org/aq phase was extracted with DCM (3 x 150 mL) . The combined organics were dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The resulting oil was purified by flash column chromatography with isocratic evolution of EtOAc (40%) and hex (60%) to provide chroman-4-carboxylic acid (1.2 g, 6.7 mmol) as a yellow oil.

  • 5
  • [ 20426-80-6 ]
  • [ 33313-82-5 ]
  • 6
  • [ 20426-80-6 ]
  • [ 107616-56-8 ]
  • 7
  • [ 20426-80-6 ]
  • (1S,2S)-2-(2-Chroman-4-yl-acetyl)-cyclopropanecarboxylic acid [ No CAS ]
  • 8
  • [ 20426-80-6 ]
  • (1R,2R)-2-(2-Chroman-4-yl-acetyl)-cyclopropanecarboxylic acid ethyl ester [ No CAS ]
  • 9
  • [ 20426-80-6 ]
  • (1R,2R)-2-(1-Amino-1-carboxy-2-chroman-4-yl-ethyl)-cyclopropanecarboxylic acid [ No CAS ]
  • 10
  • [ 20426-80-6 ]
  • (1R,2R)-2-(4-Chroman-4-ylmethyl-2,5-dioxo-imidazolidin-4-yl)-cyclopropanecarboxylic acid [ No CAS ]
  • 11
  • [ 491-37-2 ]
  • [ 20426-80-6 ]
YieldReaction ConditionsOperation in experiment
Preparation Example 7 By the reaction and treatment in the same manner as in Preparation Example 5 using 4-chromanone (5.1 g) as a starting material, chroman-4-carboxylic acid (4.1 g) was obtained. melting point: 94.3ØC
  • 12
  • [ 20426-80-6 ]
  • (R)-1-azabicyclo<2.2.2>oct-3-yl (R,S)-chromane-4-carboxylate [ No CAS ]
  • 13
  • [ 6786-30-7 ]
  • [ 20426-80-6 ]
  • 14
  • [ 20426-78-2 ]
  • [ 20426-80-6 ]
  • 15
  • [ 113967-32-1 ]
  • [ 20426-80-6 ]
  • 16
  • [ 20426-80-6 ]
  • [ 400858-39-1 ]
  • N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)chroman-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 13 By the reaction and treatment in the same manner as in Example 1 using <strong>[20426-80-6]chroman-4-carboxylic acid</strong> (0.5 g) and [(4-dimethylaminophenyl)methyl](4-isopropylphenyl)amine (0.63 g) as starting materials, N-[(4-dimethylaminophenyl)methyl]-N-(4-isopropylphenyl)chroman-4-carboxamide (0.25 g) was obtained. melting point: 110-112ØC
  • 17
  • [ 20426-80-6 ]
  • [ 6638-79-5 ]
  • [ 945390-18-1 ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 4.08333h; Example 72; rac-2-Chroman-4-ylmethyl- lH-imidazole; a) rac-Chroman-4-carboxylic acid methoxy-methyl-amide; To a solution of 500 mg (2.8 mmol) <strong>[20426-80-6]chroman-4-carboxylic acid</strong> in 10 ml dichloromethane were added 330 mg (3.2 mmol) N,O-dimethylhydroxylamine hydrochloride and 993 mg (3.2 mmol) N-(3-dimethylaminopropyl)-N'-ethyl- carbodiimide hydrochloride and the mixture stirred at ambient temperature for 5 min. Then 710 mg (0.98 ml, 10 mmol) triethylamine were added drop- wise and the resulting mixture stirred at ambient temperature for 4 hours. For workup 2M HCl solution was added, the organic solvent evaporated and the residue extracted with tert-butyl methyl ether, the combined organic phase was washed with brine, dried over Na2SO4, filtered and evaporated: 503 mg rac-<strong>[20426-80-6]chroman-4-carboxylic acid</strong> methoxy-methyl-amide as light brown oil; MS (EI): 221.2 (M+ ), 133.1 (((M - C(=O)N(CH3)OCH3)+ ), 100%).
  • 18
  • [ 20426-80-6 ]
  • diethyl (E)-chroman-4-ylidene((Z)-3-phenylallyloxy)methylphosphonate [ No CAS ]
  • 19
  • [ 20426-80-6 ]
  • [ 1401466-95-2 ]
  • 20
  • [ 20426-80-6 ]
  • C14H19O5P [ No CAS ]
  • 21
  • [ 20426-80-6 ]
  • [ 1343394-83-1 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 0.75h; To a stirred solution of (rac)-<strong>[20426-80-6]chromane-4-carboxylic acid</strong> (182 mg, 0.97 mmol) in CH2CI2 (10 mL) under N2-atmosphere was added oxalyl chloride (172 pL, 1.94 mmol), followed by DMF (4 pL, 0.0516 mmol). The reaction was left to stir at rt for 45 min. The reaction mixture was concentrated in vacuo to give (rac)-<strong>[20426-80-6]chromane-4-carboxylic acid</strong> chloride which used directly in the next step.
  • 22
  • [ 20426-80-6 ]
  • [ 21627-58-7 ]
  • [ 1392493-59-2 ]
  • 23
  • [ 20426-80-6 ]
  • 2,2-dimethyl-7-methoxy-2,3-dihydrobenzofuran-5-amine [ No CAS ]
  • N-(2,2-dimethyl-7-methoxy-2,3-dihydrobenzofuran-5-yl)benzopyran-4-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
33.3% With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃; for 1h; 0.59 g of compound 1,0.66 g of compound 22, 20 mL of dichloromethane, 0.67 g of DCC, 0.09 g of DMAP, stirred at room temperature1.0h, TLC monitoring reaction is complete; suction filter, spin dry, anhydrous ethanol to obtain 0.40 g of white solid 11, the yield of 33.3%
  • 24
  • C13H15BrO3 [ No CAS ]
  • [ 20426-80-6 ]
YieldReaction ConditionsOperation in experiment
11.2 g 16.90 g of compound 1A, 23.10 g of 1,2-propanediol,1.50 g p-toluenesulfonic acid,100mL toluene, reflux stirring 8.0h, TLC tracking ketalization reaction is completed, to be compound 1B,When the ketalization reaction solution is cooled to 80 to 90 C,1.60 g of zinc oxide, and the temperature of the bottle was increased to 126 to 130 C. The temperature was increased to 126 to 130 C. The TLC was followed by the TLC tracking and the reaction was carried out. The residue was filtered and the toluene was removed by distillation under reduced pressure to give a pale red oily substance. Then, 60 mL of a 30% aqueous solution of sodium hydroxide and 80 mL of methanol were added and the reaction was refluxed for 4.0 h. The reaction was complete with TLC. The reaction solution was charged with 100 mL of cold water The filtrate was washed with 50 mL of dichloromethane and the aqueous layer was extracted with dilute hydrochloric acid at pH 2, 100 mL of ethyl acetate, dried over anhydrous sodium sulfate, Dried to give 11.2 g of solid chroman-4-carboxylic acid in 83%
  • 25
  • [ 20426-80-6 ]
  • [ 95-54-5 ]
  • C16H16N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With 4-methyl-morpholine; HATU; In N,N-dimethyl-formamide; at 0 - 20℃; for 5h; To a solution of Example 29B (1.96 g, 11 mmol), o-phenylene diamine (3.57 g, 33 mmol) and N-methylmorpholine (3.34 g, 33 mmol) in DMF (20 mL) at 0 C was added HATU (5.02 g, 13.2 mmol). The cooling bath was removed and the reaction stirred at RT for 5 h. Water was added to the reaction and a precipitate formed. The precipitate was collected by filtration, rinsed with water and dried in vacuo at 70 C overnight to give the target compound (2.58 g, 87%) as a light yellow solid. LCMS MH+ calculated, 269.1, found 269.3.
  • 26
  • [ 20426-80-6 ]
  • [ 95-54-5 ]
  • C16H18N2O [ No CAS ]
  • 27
  • [ 20426-80-6 ]
  • [ 3652-17-3 ]
  • (5-amino-3-(pyridin-4-yl)-1H-1,2,4-triazol-1-yl)(chroman-4-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
7% Into a 50 mL of round bottom flask, was placed dihydro-2H-l-benzopyran-4-carboxylic acid (133 mg, 0.72 mmol, 3.00 equiv), N,N-dimethylformamide (5 mL), DMTMM (206 mg, 0.74 mmol, 3.00 equiv). The mixture was stirred for 30 min at room temperature. Then 3-(pyridin- 4-yl)-lH-l,2,4-triazol-5-amine (40 mg, 0.25 mmol, 1.00 equiv) was added. The resulting solution was stirred overnight at 35 C. The reaction was then quenched by the addition of water (30 mL). The resulting solution was extracted with ethyl acetate (30 mL x 3) and the organic layers combined. The resulting mixture was washed with brine (50 mL x 3). The mixture was dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was washed with 10 mL of PE/EA (30: 1) to give 5.4 mg (7%) of (5-amino-3-(pyridin-4-yl)-lH-l,2,4-triazol-l-yl)(chroman-4- yl)methanone (25) as a light yellow solid. MS (ES, m/z) [M+H]+: 322; HNMR (DMSO-d6, 400MHz, ppm): δ 8.73(d, J=4.4, 2H), 7.92(d, J=5.6, 2H), 7.88-7.84(m, 2H), 7.20-7.15(m, 2H), 6.86-6.82(m, 2H), 5.08-5.05(m, 1H), 4.26-4.19(m, 2H), 2.41-2.30(m, 2H).
  • 28
  • [ 20426-80-6 ]
  • [ 3413-28-3 ]
  • 1-chroman-4-yl(4-(4-fluorophenoxy)pipendin-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 2h; C. To a solution of chroman-4-carboxylic acid (100 mg, 0.56 mmol) and 4-(4- fluorophenoxy)piperidine (110 mg, 0.56 mmol) in DCM (10.0 mL) was added 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.11 g, 0.56 mmol), N- Hydroxybenzotrizole (0.08 g, 0.56 mmol) and triethylamine (0.11 g, 1.12 mmol). The reaction was stirred at ambient temperature for 2 h. Water (20 mL) was added and then extracted with DCM (3 X 30 mL). The combined organics were washed with brine, dried over Na2SO4. After filtered and concentrated, the residue was purified by silica column chromatography (EtOAc: hexanes = 1.5: 1) to give the desired product (100 mg, 0.28 mmol) as colorless oil.
  • 29
  • [ 20426-80-6 ]
  • 1-(chroman-4-ylmethyl)-4-(4-fluorophenoxy)piperidine hydrochloride [ No CAS ]
  • 30
  • [ 20426-80-6 ]
  • 1-(chroman-4-ylmethyl)-4-(4-fluorophenoxy)piperidine [ No CAS ]
  • 31
  • [ 20426-80-6 ]
  • [ 81151-35-1 ]
  • 1-(chroman-4-ylmethyl)-4-((4-fluorobenzyl)oxy)piperidine [ No CAS ]
  • 32
  • [ 20426-80-6 ]
  • [ 81151-35-1 ]
  • 1-chroman-4-yl(4-((4-fluorobenzyl)oxy)piperidin-1-yl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.16 g With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 20℃; for 3h; A. To a solution of <strong>[20426-80-6]chroman-4-carboxylic acid</strong> (100 mg, 0.56 mmol) in DCM (10 mL) was added 4-((4-fluorobenzyl)oxy)piperidine (0.13 g, 0.62 mmol), triethylamine (0.11 g, 1.12 mmol), HOBT (0.03 g, 1.12 mmol) and EDCI (0.2 g, 1.12 mmol). The reaction was stirred at ambient temperature for 3 h. Saturated aqueous NaHCO3 (20 mL) and DCM (100 mL) were added to the reaction vessel and the resulting biphasic mixture was transferred to a separatory funnel. The layers were separated and the organic phase was washed with saturated aqueous NaCl (2 x 20 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to provide chroman-4-yl(4-((4-fluorobenzyl)oxy)piperidin-1-yl)methanone (0.16 g, 0.43 mmol) as a yellow oil.
  • 33
  • [ 20426-80-6 ]
  • [ 606-25-7 ]
  • N-(naphthalene-1-sulfonyl)-3,4-dihydro-2H-1-benzopyran-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
A mixture of chroman-4-carboxylic acid (30 mg, 0.168 mmol) [20426-80-6], N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (64.6 mg, 0.337 mmol) and N,N-dimethylpyridin-4-amine (22.63 mg, 0.185 mmol) in dichloromethane (5 mL) was stirred at ambient temperature for 30 minutes, and <strong>[606-25-7]naphthalene-1-sulfonamide</strong> (34.9 mg, 0.168 mmol) was added. The mixture was stirred for another 4 hours, and dichloromethane (20 mL) was added. The mixture was washed with saturated aqueous NaHCO3 and brine, and concentrated. Purification via HPLC on a Phenomenex Luna C8(2) 5 um 100 Å AXIA column (30 mm*75 mm), with a gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/minute (0-1.0 minute 5% A, 1.0-8.5 minute linear gradient 5-100% A, 8.5-11.5 minute 100% A, 11.5-12.0 minute linear gradient 95-5% A) provided the title compound. 1H NMR (500 MHz, Chloroform-d) δ ppm 8.52 (dd, J=7.4, 1.3 Hz, 1H), 8.40 (s, 1H), 8.33-8.28 (m, 1H), 8.18-8.13 (m, 1H), 8.02-7.97 (m, 1H), 7.68-7.60 (m, 3H), 7.25 (dddd, J=8.2, 7.1, 1.8, 0.5 Hz, 1H), 6.91-6.80 (m, 3H), 4.01 (dddd, J=11.5, 4.7, 3.6, 1.1 Hz, 1H), 3.68 (ddd, J=11.4, 10.5, 2.7 Hz, 1H), 3.57 (t, J=5.2 Hz, 1H), 2.17 (dtd, J=14.1, 4.6, 2.7 Hz, 1H), 2.07-2.00 (m, 1H). MS (ESI+) m/z 368 (M+H)+.
  • 34
  • [ 493-08-3 ]
  • [ 124-38-9 ]
  • [ 20426-80-6 ]
  • 35
  • [ 20426-80-6 ]
  • 5-(2-fluoro-4-nitrophenyl)-1,3-oxazole [ No CAS ]
  • N-(3-fluoro-4-(oxazol-5-yl)phenyl)chromane-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
35% 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 16h; To a stirred solution of 3-chloro-4- (oxazol-5-yl) aniline(200 mg, 1.03 mmol) and 6-methoxy-3, 4-dihydro-2H-l- benzopyran-3-carboxylic acid (278.76 mg, 1.34 mmol) in DMF (2 mL) were added DIPEA (0.52 mL) and HATU (784mg, 2.06 mmol) at room temperature and the reaction was stirred for 16 h at rt . After completion of the reaction, the reaction mixture was purified by preparative HPLC to yield N-( 3- chloro-4- (oxazol-5-yl) phenyl) -6-methoxychromane-3- carboxamide (143 mg, 36%) . Analytical HPLC Method A. Rt: 1.73 min; MS: 385.2 (M+H) .
35% 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 16h; To a stirred solution of 3-fluoro-4-(1,3-oxazol-5- yl)aniline (150 mg, 0.84 mmol) and 3,4-dihydro-2H-1- benzopyran-4-carboxylic acid (195.21 mg, 1.09 mmol) in DMF (2 mL) were added DIPEA (0.44 mL) and HATU (640 mg, 1.68 mmol) at room temperature and the reaction was stirred for 16 h at room temperature. After completion of the reaction, the reaction mixture was purified by preparative HPLC to yield N-(3-fluoro-4-(oxazol-5- yl)phenyl)chromane-4-carboxamide (102 mg, 35%). Analytical HPLC Method A. Rt: 1.50 min; MS: 339.2(M+H).
  • 36
  • [ 20426-80-6 ]
  • [ 198821-76-0 ]
  • N-(3-chloro-4-(oxazol-5-yl)phenyl)chromane-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% 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 16h; To a stirred solution of 3-chloro-4- (oxazol-5-yl) aniline (100 mg, 0.51 mmol) and 3, 4-dihydro-2H-l-benzopyran-4- carboxylic acid (119.4 mg, 0.67 mmol) in DMF (1 mL) were added DIPEA (0.26 mL) and HATU (392 mg, 1.03 mmol) at room temperature and the reaction was stirred for 16 h at rt. After completion of the reaction, the reaction mixture was purified by preparative HPLC to yield AT- (3-chloro-4- (oxazol- 5-yl) phenyl) chromane-4-carboxamide (56 mg, 30%). Analytical HPLC Method A. Rt: 1.55 min; MS: 355.2 (M+H) .
  • 37
  • [ 20426-80-6 ]
  • [ 198821-79-3 ]
  • N-(3-methoxy-4-(oxazol-5-yl)phenyl)chromane-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44% 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 12h; To a stirred solution of 3-methoxy-4- (oxazol-5-yl) aniline (75 mg, 0.395 mmol) and 3, 4-dihydro-2H-l-benzopyran-4- carboxylic acid (105.3 mg, 0.592 mmol) in DMF (3 mL) were added DIPEA (0.15 mL) and HATU (226 mg, 0.592 mmol) at room temperature and the reaction was stirred for 12 h at rt. After completion of the reaction, the reaction mixture was purified by preparative HPLC to yield N-(3-methoxy-4- (oxazol-5-yl) phenyl) chromane-4-carboxamide (60.07 mg, 44%). Analytical HPLC Method A. Rt: 1.42 min; MS: 351.2 (M+H) .
44% 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 16h; To a stirred solution of 3-methoxy-4-(oxazol-5-yl)aniline (75 mg, 0.395 mmol) and 3,4-dihydro-2H-1-benzopyran-4- carboxylic acid (105.3 mg, 0.592 mmol) in DMF (3 mL) were added DIPEA (0.15 mL) and HATU (226 mg, 0.592 mmol) at room temperature and the reaction was stirred for 12 h at room temperature. After completion of the reaction, the reaction mixture was purified by preparative HPLC to yield N-(3-methoxy-4-(oxazol-5-yl)phenyl)chromane-4-carboxamide (60.07 mg, 44%). Analytical HPLC Method A. Rt: 1.42 min; MS: 351.2 (M+H).
  • 38
  • [ 20426-80-6 ]
  • N-[8-(3,5-dichlorophenyl)-4-(dimethylamino)-3-quinolyl]chromane-4-carboxamide [ No CAS ]
  • 39
  • [ 20426-80-6 ]
  • (4R)-N-[8-(3,5-dichlorophenyl)-4-(dimethylamino)-3-quinolyl]chromane-4-carboxamide [ No CAS ]
  • (4S)-N-[8-(3,5-dichlorophenyl)-4-(dimethylamino)-3-quinolyl]chromane-4-carboxamide [ No CAS ]
  • 40
  • [ 20426-80-6 ]
  • 8-(2,3-dichlorophenyl)-4-morpholinoquinolin-3-amine [ No CAS ]
  • (S)-N-(8-(2,3-dichlorophenyl)-4-morpholinoquinolin-3-yl)chromane-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; 8-(2,3-Dichlorophenyl)-4-morpholinoquinolin-3-amine (60 mg, 0.16 mmol), chromane-4- carboxylic acid (29 mg, 0.16 mmol), EDC (46 mg, 0.24 mmol) and DMAP (10 mg, 0.08 mmol) were placed in a vial, DMF (1 ml) was added and the mixture stirred at ambient temperature overnight. The mixture was diluted with a mixture of acetonitrile and water (1:1) and purified by preparative HPLC (Waters XBridge, eluting with a gradient of acetonitrile containing 10% THF and water containing 0.1% formic acid) yielding 30 mg of a solid (34% yield). MS (ESI) m/z: 532.1 [M+H]+.
  • 41
  • [ 20426-80-6 ]
  • 8-(2,3-dichlorophenyl)-7-fluoro-N<SUP>4</SUP>,N<SUP>4</SUP>-dimethylquinoline-3,4-diamine [ No CAS ]
  • N-(8-(2,3-dichlorophenyl)-4-(dimethylamino)-7-fluoroquinolin-3-yl)chroman-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.8 mg With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In toluene; at 20℃; for 6h; To a solution of 8-(2,3-dichlorophenyl)-7-fluoro-/V‘,/V‘-dimethylquinoline-3, 4-diamine (100 mg, 0.29 mmol) in toluene (10 mL) was added <strong>[20426-80-6]chromane-4-carboxylic acid</strong> (76 mg, 0.43 mmol), N,N- diisopropylethylamine (369 mg, 2.9 mmol) and T3P (363 mg, 1.1 mmol). The resulting mixture was stirred for 6 hours at room temperature. Upon completion of reaction, the solvent was removed in vacuum. The residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1:2), and further purified by Prep- HPLC (Mobile Phase A: water (10 mmol/L NH4HCO3), Mobile Phase B: ACN; Gradient: 68% B to 77% B in 7 min; Rt = 6.27 min) to give 83.8 mg (99% purity, 57% yield) of the product as an off- white solid. (0792) -NMR (400 MHz, DMSO-£ tf): d ppm = 2.20-2.24 (m, 2H), 3.03 (s, 6H), 4.03-4.06 (m, 1H), 4.17- 4.21 (m, 1H), 4.35-4.38 (m, 1H), 6.80-6.83 (m, 1H), 6.87-6.92 (m, 1H), 7.13-7.18 (m, 1H), 7.24-7.27 (m, 1H), 7.37-7.40 (m, 1H), 7.45-7.50 (m, 1H), 7.60-7.64 (m, 1H), 7.73-7.76 (m, 1H), 8.23-8.28 (m, 1H) , 8.52 (s, 1H), 9.97 (s, 1H). (0793) LC-MS (Analytical Method A, 0-2.00 min 5-95% B): R = 1.81 min; MS (ESIpos): m/z = 510 [M+H]+.
  • 42
  • [ 20426-80-6 ]
  • N<SUP>4</SUP>,N<SUP>4</SUP>-dimethyl-8-(2,3,5-trifluorophenyl)quinoline-3,4-diamine [ No CAS ]
  • N-(4-(dimethylamino)-8-(2,3,5-trifluorophenyl)quinolin-3-yl)chroman-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
44.6 mg With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; toluene; at 100℃; for 1h; To a solution of N4, A4-dimethyl-8-(2, 3, 5-trifluorophenyl)quinoline-3 ,4-diamine (200 mg, 0.40 mmol) in toluene (20 mL) were added <strong>[20426-80-6]chroman-4-carboxylic acid</strong> (144 mg, 0.81 mmol), T3P (50% in EA, 480 mg, 0.81 mmol) and DIEA (490 mg, 4.0 mmol). The resulting mixture was stirred at 100 C for 1 hour. After cooled to room temperature, the solvent was removed in vacuum. The residue was purified by Prep- TLC (petroleum ether: ethyl acetate = 1: 1), then further purified by /Ytyi-HPLC (Mobile Phase A: Water (10 mmol/L NH4HCO3), Mobile Phase B: ACN; Gradient: 50% B to 90% B in 8 min; Rt = 6.80 min) to give 44.6 mg (97% purity, 22% yield) of the product as a light yellow solid. (0637) -NMR (400 MHz, DMSO-£ tf): d [ppm = 2.19-2.23 (m, 2H), 3.02 (s, 6H), 4.06 (t, 1H), 4.17-4.22 (m, 1H), 4.34-4.39 (m, 1H), 6.82 (d, 1H), 6.90 (t, 1H), 7.14-7.18 (m, 1H), 7.20-7.23 (m, 1H), 7.26-7.28 (m, (0638) 1H), 7.56-7.61 (m, 1H), 7.64-7.72 (m, 2H), 8.20-8.23 (m, 1H), 8.60 (s, 1H), 9.99 (s, 1H). (0639) LC-MS (Analytical Method A, 0.01-2.00 min 5% to 95%B, 2.00-2.60 min 95%B): Rt = 1.78 min; MS (ESIpos): m/z = 478 [M+H]+.
  • 43
  • [ 20426-80-6 ]
  • 4-morpholino-8-(2,3,5-trifluorophenyl)quinolin-3-amine [ No CAS ]
  • N-(4-morpholino-8-(2,3,5-trifluorophenyl)quinolin-3-yl)chroman-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.6 mg With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; toluene; at 100℃; for 1h; To a solution of 4-morpholino-8-(2,3,5-trifluorophenyl)quinolin-3-amine (200 mg, 0.39 mmol) in toluene (30 mL) were added <strong>[20426-80-6]chroman-4-carboxylic acid</strong> (139 mg, 0.78 mmol), T3P (50% in EA, 496 mg, 0.78 mmol) and DIEA (503 mg, 3.9 mmol). The resulting mixture was stirred at 100 C for 1 hour. After cooled to room temperature, the solvent was removed in vacuum. The residue was purified by Prep- TLC (petroleum ether: ethyl acetate = 1: 1), then further purified by Prep- HPLC (Mobile Phase A: Water (10 mmol/L NH4HCO3), Mobile Phase B: ACN; Gradient: 45% B to 80% B in 7 min; Rt: 6.72 min) to give 65.6 mg (99% purity, 32% yield) of the product as an off-white solid. (0655) -NMR (400 MHz, DMSO-£ tf): d [ppm] = 2.23-2.25 (m, 2H), 3.29-3.30 (m, 4H), 3.81-3.83 (m, 4H), 4.05 (t, 1H), 4.20 (t, 1H), 4.38 (t, 1H), 6.82 (d, 1H), 6.92 (d, 1H), 7.10-7.16 (m, 2H), 7.29 (d, 1H), 7.68- 7.70 (m, 1H), 7.72-7.76 (m, 2H), 8.26-8.28 (m, 1H), 8.58 (s, 1H), 10.06 (s, 1H). (0656) LC-MS (Analytical Method A, 0.01-2.00 min 5% to 95%B, 2.00-2.60 min 95%B): R = 1.90 min; MS (ESIpos): m/z = 520 [M+H]+.
  • 44
  • [ 20426-80-6 ]
  • 4-ethyl-8-(2,3,5-trifluorophenyl)quinolin-3-amine [ No CAS ]
  • N-(4-ethyl-8-(2,3,5-trifluorophenyl)quinolin-3-yl)chromane-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
174.4 mg With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; toluene; at 100℃; for 1h; To a solution of 4-ethyl-8-(2,3,5-trifluorophenyl)quinolin-3-amine (230 mg, 73% purity, 0.56 mmol) in toluene (15 mL) were added 1, 2, 3, 4-tetrahydronaphthalene-l -carboxylic acid (149 mg, 0.83 mmol), T3P (50% in EA, 844 mg, 2.2 mmol) and triethylamine (562 mg, 5.6 mmol). The resulting mixture was stirred at 100 C for 1 hour. After cooled to room temperature, the solvent was removed and ethyl acetate was added. The resulting mixture was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum. The residue was purified by Prep- HPLC (Mobile Phase A: Water (10 mmol/L NH4HCO3), Mobile Phase B: ACN; Gradient: 50% B to 87% B in 7 min; Rt = 6.72 min) to afford 174.4 mg (99% purity, 67% yield) of the product as a light yellow solid. -NMR (400 MHz, DMSO-ritf): d ppm = 1.22 (t, 3H), 2.21-2.25 (m, 2H), 3.12-3.16 (m, 2H), 4.06- 4.10 (m, 1H), 4.18-4.22 (m, 1H), 4.38-4.43 (m, 1H), 6.81-6.84 (m, 1H), 6.89-6.95 (m, 1H), 7.14-7.19 (m, 1H), 7.23-7.33 (m, 2H), 7.60-7.63 (m, 1H), 7.74-7.81 (m, 2H), 8.30-8.33 (m, 1H), 8.74 (s, 1H), 10.19 (s, 1H). (0672) LC-MS (Analytical Method A, 0.01-2.00 min 5-95% B, 2.00-2.60 min 95% B): Rt = 1.97 min; MS (ESIpos): m/z = 463 [M+H]+.
  • 45
  • [ 20426-80-6 ]
  • 4-(tetrahydro-2H-pyran-4-yl)-8-(2,3,5-trifluorophenyl)quinolin-3-amine [ No CAS ]
  • N-(4-(tetrahydro-2H-pyran-4-yl)-8-(2,3,5-trifluorophenyl)quinolin-3-yl)chroman-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84.8 mg With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; at 100℃; for 1h; To a solution of 4-(tctrahydro-2 /-pyran -4-yl)-8-(2.3.5-trifluorophcnyl)quinol in-3 -amine (175 mg, 0.44 mmol) in toluene (20 mL) were added <strong>[20426-80-6]chroman-4-carboxylic acid</strong> (156 mg, 0.9 mmol), T3P (50% in EA, 560 mg, 0.88 mmol) and DIEA (568 mg, 4.4 mmol). The resulting mixture was stirred at 100 C for 1 hour. After cooled to room temperature, the solvent was removed in vacuum. The residue was purified by Prep-TLC (petroleum ether: ethyl acetate = 1:1), and further purified by Prep- HPLC (Mobile Phase A: Water (10 mmol/L NH4HCO3), Mobile Phase B: ACN; Gradient: 45% B to 85% B in 7 min; Rt = 6.52 min) to give 84.8 mg (97% purity, 36% yield) of the product as an off-white solid. (0683) -NMR (400 MHz, DMSO-£/tf): d [ppm] = 1.62-1.63 (m, 2H), 2.23-2.26 (m, 2H), 2.41-2.50 (m, 2H), 3.38-3.40 (m, 1H), 3.48-3.50 (m, 1H), 3.66-3.67 (m, 1H), 4.00-4.08 (m, 3H), 4.20-4.23 (m, 1H), 4.41- 4.44 (m, 1H), 6.83 (d, 1H), 6.92 (t, 1H), 7.15-7.19 (m, 1H), 7.23-7.25 (m, 1H), 7.38 (d, 1H), 7.59-7.62 (m, 1H), 7.74-7.80 (m, 2H), 8.56-8.58 (m, 1H), 8.63 (s, 1H), 10.29 (s, 1H). (0684) LC-MS (Analytical Method A, 0.01-2.00 min 5% to 95%B, 2.00-2.60 min 95%B): R = 1.88 min; MS (ESIpos): m/z = 519 [M+H]+.
  • 46
  • [ 20426-80-6 ]
  • 7-fluoro-4-(tetrahydro-2H-pyran-4-yl)-8-(2,3,5-trifluorophenyl)quinolin-3-amine [ No CAS ]
  • N-(7-fluoro-4-(tetrahydro-2H-pyran-4-yl)-8-(2,3,5-trifluorophenyl)quinolin-3-yl)chroman-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; toluene; at 100℃; for 1h; To a solution of 7-fluoro-4-(tctrahydro-2//-pyran-4-yl)-8-(2.3.5-trifluorophcnyl)quinolinc3-aminc (251 mg, 0.58 mmol) in toluene (20 mL) were added <strong>[20426-80-6]chroman-4-carboxylic acid</strong> (207 mg, 1.2 mmol), T3P (50% in EA, 849 mg, 1.2 mmol) and DIEA (861 mg, 5.8 mmol). The resulting mixture was stirred at 100 C for 1 hour. After cooled to room temperature, the solvent was removed in vacuum. The residue was purified by Prep-TLC (petroleum ether: ethyl acetate = 1:1), then further purified by Prep- HPLC (Mobile Phase A: Water (0.05% NH3H2O), Mobile Phase B: ACN; Gradient: 53% B to 63% B in 7 min; Rt = 6.08 min) to give 46.6 mg (94% purity, 14% yield) of the product as an off-white solid. (0699) -NMR (400 MHz, DMSO-dtf): d [ppm] = 2.55-2.65 (m, 2H), 2.15-2.20 (m, 2H), 2.38-2.40 (m, 2H), 3.32-3.38 (m, 1H), 3.44-3.50 (m, 1H), 3.66-3.67 (m, 1H), 4.00-4.07 (m, 3H), 4.18-4.23 (m, 1H), 4.40- 4.45 (m, 1H), 6.82 (d, 1H), 6.92 (t, 1H), 7.17 (t, 1H), 7.31-7.38 (m, 2H), 7.64-7.69 (m, 1H), 7.70-7.78 (m, 1H), 8.67 (t, 2H), 10.28 (s, 1H). (0700) LC-MS (Analytical Method A, 0.01-2.00 min 5% to 95%B, 2.00-2.60 min 95%B): Rt = 1.88 min; MS (ESIpos): m/z = 537 [M+H]+.
  • 47
  • [ 20426-80-6 ]
  • 7-fluoro-N<SUP>4</SUP>,N<SUP>4</SUP>-dimethyl-8-(2,3,5-trifluorophenyl)quinoline-3,4-diamine [ No CAS ]
  • N-(4-(dimethylamino)-7-fluoro-8-(2,3,5-trifluorophenyl)quinolin-3-yl)chroman-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In toluene; at 100℃; for 2h; To a solution of 7-fluoro-/V ,/V -dimethyl-8-(2, 3, 5-trifluorophenyl)quinoline-3 ,4-diamine (140 mg, 0.42 mmol) in toluene (25 mL) was added <strong>[20426-80-6]chromane-4-carboxylic acid</strong> (111 mg, 0.62 mmol), N,N- diisopropylethylamine (538 mg, 4.2 mmol) and T3P (530 mg, 1.7 mmol). The resulting mixture was stirred for 2 hours at 100 C. After cooled to room temperature, the solvent was removed in vacuum. The residue was purified by silica gel chromatography (ethyl acetate: petroleum ether = 1:2), and further purified by Prep- HPLC (Mobile Phase A: Water (10 mmol/L NH4HCO3), Mobile Phase B: ACN; Gradient: 55% B to 75% B in 7 min; Rt = 6.72 min) to give 95.9 mg (99% purity, 46% yield) of the product as an off-white solid. -NMR (300 MHz, DMSO-£ tf): d ppm = 2.08-2.32 (m, 2H), 3.02 (s, 6H), 4.02-4.07 (m, 1H), 4.15- 4.22 (m, 1H), 4.33-4.41 (m, 1H), 6.79-6.83 (m, 1H), 6.86-6.92 (m, 1H), 7.12-7.18 (m, 1H), 7.24-7.30 (m, 2H), 7.60-7.71 (m, 2H), 8.25-8.31 (m, 1H), 8.57 (s, 1H), 10.00 (s, 1H). (0716) LC-MS (Analytical Method A, 0-2.00 min 5-95% B): R = 1.88 min; MS (ESIpos): m/z = 496 [M+H]+.
  • 48
  • [ 20426-80-6 ]
  • 4-ethyl-7-fluoro-8-(2,3,5-trifluorophenyl)quinolin-3-amine [ No CAS ]
  • N-(4-ethyl-7-fluoro-8-(2,3,5-trifluorophenyl)quinolin-3-yl)chromane-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
22% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; toluene; at 100℃; for 1h; To a solution of 4-ethyl-7-fluoro-8-(2,3,5-trifluorophenyl)quinolin-3-amine (190 mg, 0.85 mmol) in toluene (5 mL) was added 1,2,3,4-tetrahydronaphthalene-l-carboxylic acid (227 mg, 1.3 mmol), T3P (50% in ethyl acetate, 755 mg, 3.4 mmol ) and triethylamine (858 mg, 8.5 mmol). The resulting mixture was stirred at 100 C for 1 hour. After cooled to room temperature, the solvent was removed and then ethyl acetate was added. The resulting mixture was washed with water, brine, dried over anhydrous sodium sulfate, fdtered and concentrated under vacuum. The residue was purified by Prep- HPLC (Mobile Phase A: Water (10MMOL/L NH4HCO3), Mobile Phase B: ACN; Gradient: 55% B to 65% B in 8 min; RT = 7.72 min) to give 93.2 mg (98% purity, 22% yield) of the product as an off-white solid. -NMR (400 MHz, DMSO-£/tf): d ppm = 1.19-1.23 (m, 3H), 2.23 (d, 2H), 3.13-3.18 (m, 2H), 4.06- 4.09 (m, 1H), 4.18-4.22 (m, 1H), 4.39-4.42 (m, 1H), 6.81 (d, 1H), 6.90 (d, 1H), 6.93 (d, 1H), 7.16-7.18 (m, 2H), 7.31 (d, 1H), 7.68-7.70 (m, 1H), 7.75-7.79 (m, 1H), 8.41-8.45 (m, 1H), 10.21 (s, 1H). (0733) LC-MS (Analytical Method A, 0.01-2.00 min 5-95% B, 2.00-2.60 min 95% B): R = 1.94 min; MS (ESIpos): m/z = 481 (M+H)+.
  • 49
  • [ 20426-80-6 ]
  • 8-(3,5-dichlorophenyl)-7-fluoro-4-morpholinoquinolin-3-amine [ No CAS ]
  • N-(8-(3,5-dichlorophenyl)-7-fluoro-4-morpholinoquinolin-3-yl)chromane-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
38.8% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; toluene; at 100℃; for 2h; To a solution of 8-(3,5-dichlorophenyl)-7-fluoro-4-morpholinoquinolin-3-amine (150 mg, 0.38 mmol) in toluene (10 mL) was added <strong>[20426-80-6]chromane-4-carboxylic acid</strong> (136 mg, 0.76 mmol), T3P (50% in ethyl acetate, 486 mg, 1.5 mmol) and A'A'-diisopropylcthylaminc (554 mg, 3.8 mmol). The resulting mixture was stirred at 100 C for 2 hours. After cooled to room temperature, the reaction mixture was concentrated under vacuum. The residue was purified by silica gel chromatography (petroleum ether: ethyl acetate = 3:2), then further purified by Prep- HPLC [Mobile Phase A: Water (10 mmol/L NH4HCO3), Mobile Phase B: ACN; Gradient: 48% B to 88% B in 8 min; Rt = 7.90 min] to give 82.9 mg (38.8% yield) of the product as a white solid. -NMR (300 MHz, DMSO-£ tf): d ppm = 2.25-2.26 (m, 2H), 3.32 (t, 4H), 3.83 (t, 4H), 4.06 (t, 1H), 4.25 (t, 1H), 4.44 (t, 1H), 6.82 (d, 1H), 6.85 (d, 1H), 6.92 (t, 1H), 7.18 (t, 1H), 7.54 (s, 2H), 7.66-7.71 (m, 2H), 8.28 (d, 1H), 8.60 (s, 1H), 10.1 (s, 1H). (0760) LC-MS (Analytical Method A, 0-3.00 min 5-95% B): R = 2.12 min; MS (ESIpos): m/z = 552 [M+H]+.
  • 50
  • [ 20426-80-6 ]
  • 8-(3,5-dichlorophenyl)-4-ethyl-7-fluoroquinolin-3-amine [ No CAS ]
  • N-(8-(3,5-dichlorophenyl)-4-ethyl-7-fluoroquinolin-3-yl)chromane-4-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27.5% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In ethyl acetate; toluene; at 100℃; for 2h; To a solution of 8-(3,5-dichlorophenyl)-4-ethyl-7-fluoroquinolin-3-amine (130 mg, 0.4 mmol ) in toluene (7.0 mL) was added <strong>[20426-80-6]chromane-4-carboxylic acid</strong> (138 mg, 0.78 mmol), T3P (50% in ethyl acetate, 987 mg, 1.6 mmol) and A'A'-diisopropylethylamine (500 mg, 3.9 mmol). The resulting mixture was stirred for 2 hours at 100 C. After cooled to room temperature, the mixture was concentrated under vacuum. The residue was purified by silica gel chromatography (petroleum ether: ethyl acetate = 3: 2) and further purified by Prep- HPLC [Mobile Phase A:Water(10 mmol/L NH4HCO3), Mobile Phase B:ACN; Gradient:72 B to 82 B in 7 min; Rt:5.13 min] to give 53.1 mg (27.5% yield) of the product as a white solid. -NMR (400 MHz, DMSO-£/tf): d [ppm = 1.12 (t, 3H), 2.22-2.23 (q, 2H), 3.10-3.15 (m, 2H), 4.07 (t, 1H), 4.19-4.20 (m, 1H), 4.40 (t, 1H), 6.81 (d, 1H), 6.90 (t, 1H), 7.14 (t, 1H), 7.30 (d, 1H), 7.55 (s, 2H), 7.69-7.73 (m, 2H), 8.32-8.36 (m, 1H), 8.75 (s, 1H), 10.18 (s, 1H). (0775) LC-MS (Analytical Method A, 0-3.00 min 5-95% B): R = 2.14 min; MS (ESIpos): m/z = 495 [M+H]+.
  • 51
  • [ 20426-80-6 ]
  • tert-butyl 2-(2-(2-isopropylphenyl)-6-oxopiperazin-1-yl)-7-azaspiro[3.5]nonane-7-carboxylate [ No CAS ]
  • tert-butyl 2-(4-(chroman-4-carbonyl)-2-(2-isopropylphenyl)-6-oxopiperazin-1-yl)-7-azaspiro[3.5]nonane-7-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.1 g With N-ethyl-N,N-diisopropylamine; HATU; at 20℃; for 3h; To a solution of <strong>[20426-80-6]chroman-4-carboxylic acid</strong> (646 mg, 3.62 mmol) in DMF (20 mL) was added DIEA (585 mg, 4.53 mmol) , HATU (1.03 g, 2.72 mmol) and tert-butyl 2- (2- (2-isopropylphenyl) -6-oxopiperazin-1-yl) -7-azaspiro [3.5] nonane-7-carboxylate (1.0 g, 2.26 mmol) was added at 20 for 3 hrs. The reaction mixture was poured into water (50 mL) , extracted with EtOAc (50 mL × 3) . The combined organic phases were washed with brine, dried with anhydrous Na2SO4, filtered and concentrated in vacuum. The residue was purified by column chromatography (silica gel, eluent: PE/EA (v/v) = 100/1 to 1/1) to give tert-butyl 2- (4- (chroman-4-carbonyl) -2- (2-isopropylphenyl) -6-oxopiperazin-1-yl) -7-azaspiro [3.5] nonane-7-carboxylate (1.1 g, 1.83 mmol, yield: 82%) as a white solid.1H NMR (400 MHz, DMSO-d6) δ ppm: 7.50-7.39 (m, 1H) , 7.37-7.19 (m, 2H) , 7.17 (s, 1H) , 7.04-6.90 (m, 1H) , 6.89-6.69 (m, 2H) , 6.68-6.54 (m, 1H) , 5.41-5.27 (m, 1H) , 4.82-4.45 (m, 2H) , 4.37-4.15 (m, 1H) , 4.13-3.94 (m, 2H) , 3.92-3.70 (m, 1H) , 3.60-3.38 (m, 2H) , 3.20 (br s, 2H) , 3.09 (br s, 2H) , 2.17-1.73 (m, 4H) , 1.68-1.52 (m, 2H) , 1.49-1.39 (m, 2H) , 1.35 (s, 9H) , 1.30-1.15 (m, 8H) , 0.91-0.56 (m, 1H) .
  • 52
  • chroman-4-carbonitrile [ No CAS ]
  • [ 20426-80-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In methanol; water; at 100℃; for 12h; To a mixture of chroman-4-carbonitrile (1.6 g, 10.06 mmol) in MeOH (30 mL) and H2O (5 mL) was added NaOH (2.0 g, 50.26 mmol) at 20 . The mixture was stirred at 100 for 12 hrs. The reaction solution was added HCl (1 M) to pH = 1, extracted with EtOAc (50 mL × 3) . The combined organic phases were washed with brine (20 mL) , dried with anhydrous Na2SO4, filtered and concentrated in vacuum to give chroman-4-carboxylic acid (850 mg, crude) as a yellow oil.1H NMR (400 MHz, DMSO-d6) δ ppm: 12.77-12.47 (m, 1H) , 7.20 (d, J= 7.6 Hz, 1H) , 7.16-7.09 (m, 1H) , 6.85 (m, 1H) , 6.79-6.74 (m, 1H) , 4.20-4.09 (m, 2H) , 3.75 (m, 1H) , 2.21-2.01 (m, 2H) .
  • 53
  • [ 20426-80-6 ]
  • tert-butyl 2-(4-(chroman-4-ylmethyl)-2-(2-isopropylphenyl)piperazin-1-yl)-7-azaspiro[3.5]nonane-7-carboxylate [ No CAS ]
  • 54
  • [ 20426-80-6 ]
  • 2-(4-(chroman-4-ylmethyl)-2-(2-isopropylphenyl)piperazin-1-yl)-7-azaspiro[3.5]nonane [ No CAS ]
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Chemical Structure| 860265-69-6

[ 860265-69-6 ]

(1R,1aR,7bS)-1,1a,2,7b-Tetrahydrocyclopropa[c]chromene-1-carboxylic acid

Similarity: 0.93

Chemical Structure| 1000414-37-8

[ 1000414-37-8 ]

2-(6-Hydroxy-2,3-dihydrobenzofuran-3-yl)acetic acid

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Chemical Structure| 1221498-01-6

[ 1221498-01-6 ]

2-(6-Methyl-2,3-dihydrobenzofuran-3-yl)acetic acid

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Related Parent Nucleus of
[ 20426-80-6 ]

Other Aromatic Heterocycles

Chemical Structure| 102540-00-1

[ 102540-00-1 ]

2-Oxochroman-4-carboxylic acid

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Chemical Structure| 860265-69-6

[ 860265-69-6 ]

(1R,1aR,7bS)-1,1a,2,7b-Tetrahydrocyclopropa[c]chromene-1-carboxylic acid

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Chemical Structure| 1225503-10-5

[ 1225503-10-5 ]

2,2-Dimethylchroman-4-carboxylic acid

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Chemical Structure| 944899-30-3

[ 944899-30-3 ]

6-Methylchroman-3-carboxylic acid

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Chemical Structure| 1260606-65-2

[ 1260606-65-2 ]

(S)-6-Methylchroman-3-carboxylic acid

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