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Structure of 932705-78-7

Chemical Structure| 932705-78-7

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Product Details of [ 932705-78-7 ]

CAS No. :932705-78-7
Formula : C7H6FNO2
M.W : 155.13
SMILES Code : O=C(O)C1=CN=C(C)C(F)=C1
MDL No. :MFCD16988742
InChI Key :LKTUUSBGSVWDAL-UHFFFAOYSA-N
Pubchem ID :57516329

Safety of [ 932705-78-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H312-H332
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Application In Synthesis of [ 932705-78-7 ]

* 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 [ 932705-78-7 ]

[ 932705-78-7 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 932705-78-7 ]
  • [ 6638-79-5 ]
  • [ 932705-81-2 ]
  • 2
  • di-tert-butyl [5-(tert-butoxycarbonyl)-3-fluoropyridin-2-yl]malonate [ No CAS ]
  • [ 932705-78-7 ]
  • 3
  • [ 932705-78-7 ]
  • [ 100-51-6 ]
  • [ 1253383-92-4 ]
YieldReaction ConditionsOperation in experiment
To a solution of 5-fluoro-6-methyl-nicotinic acid (0.17 g, 1.10 mmol) in toluene (10 mL) is added diphenylphosphoryl azide (0.30 mL, 1.3 mmol) followed by N,N- diisopropylethylamine (0.21 mL, 1.20 mmol). The mixture is stirred at room temperature for 1 h then benzyl alcohol (0.14 mL, 1.30 mmol) is added and the reaction mixture is heated to 110 0C for 2 h. The mixture is cooled to room temperature and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography using a 0-30% gradient of EtO Ac/heptanes to provide 0.196 g of (5-fluoro-6-methyl-pyridin-3- yl)-carbamic acid benzyl ester as a solid.
  • 4
  • [ 1253383-91-3 ]
  • [ 932705-78-7 ]
YieldReaction ConditionsOperation in experiment
800 mg With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 1h; To a solution of methyl 5-fluoro-6-methylnicotinate (D16 2.3 g) in THF (10 mL) and methanol (10 mL) was added a solution of NaOH (0.707 g) in water (5 mL) . The mixture was stirred at RT for 1 hour and then concentrated under vacuum. To the residue was added water (5 mL) . The pH of the mixture was adjusted to 3. The solid was collected and dried under vacuum to afford the title compound (800 mg) as a white solid.1H NMR (400 MHz DMSO-d6) 8.83 (s 1H) 8.00 (dd J1.2 Hz 9.6 Hz 1H) 2.57 (s 3H) . MS (ESI) C7H6FNO2requires 155 found 156 [M+H]+.
800 mg With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20℃; for 1h; To a solution of methyl 5-fluoro-6-methylnicotinate (1)18, 2.3 g) in TifF (10 mL) and methanol (10mL) was added a solution of NaOH (0.707 g) in water (5 mL). The mixture was stirred at RT for 1hour, and then concentrated under vacuum. To the residue was added water (5 mL). The pH of themixture was adjusted to 3. The solid was collected and dried under vacuum afford the titlecompound (800 mg) as white solid. ‘H NMR (400 MHz, DMSO-d6): 8.83 (s, 111), 8.00 (dd, J= 1.2 Hz, 9.6 Hz, 1H), 2.57 (s, 3H). MS (ESI): C7H6FNO2 requires 155; found 156 [M+H].
800 mg With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 1h; Description 1135-Fluoro-6-methylnicotinic acid (D113) To a solution of methyl 5-fluoro-6-methylnicotinate (Dl 12, 2.3 g) in THF (10 mL) and methanol (10 mL) was added a solution of NaOH (0.707 g) in water (5 mL). The mixture was stirred at RT for 1 hour, and then concentrated under vacuum. To the residue was added water (5 ml). The pH ofthe mixture was adjusted to 3. The solid was collected and dried under vacuum to afford the title compound (800 mg) as white solid. ‘H NMR (400 MHz, DMSO-d6): 8.83 (s, 1H), 8.00 (dd, J= 9.6, 1.2 Hz, 1H), 2.57 (s, 311). MS (ESI): C7H6FNO2 requires 155; found 156 {M+H].
800 mg With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20℃; for 1h; In the containment5-fluoro-6-methylnicotinic acid methyl ester (D16, 2.3 g)Of THF (10 mL) with methanol (10 mL)A solution of NaOH (0.707 g) in water (5 mL) was added to the solution.The mixture was stirred at room temperature for 1 hour,Then concentrated in vacuo. Add water (5 mL) to the residue.Adjust the pH of the mixture to 3.Collect solid, vacuum dry,To give the title compound (800 mg) as a white solid
To a suspension of 5-fluoro-6-methyl-nicotinic acid methyl ester (0.21 g, 1.24 mmol) in a 1:1 mixture of MeOH: water (20 mL) is added sodium hydroxide as a 10% aqueous solution (1.0 mL, 2.5 mmol). The mixture is heated to 50 0C for 1 h then cooled to room temperature and concentrated under reduced pressure to remove volatile organics. The pH of the resulting solution is adjusted to slightly acidic (approximately pH 5) by the addition of a 2N solution of HCl. The mixture is extracted with EtOAc and the combined organic phase is dried over anhydrous sodium sulfate and concentrated to provide 0.170 g of S-fluoro-β-methyl-nicotinic acid as a solid.

  • 5
  • [ 932705-78-7 ]
  • [ 124-41-4 ]
  • [ 7442-24-2 ]
YieldReaction ConditionsOperation in experiment
2.45 g In N,N-dimethyl-formamide; at 140℃; for 16h; The mixture of <strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (D17 3.5 g) and sodium methanolate (12.2 g) in DMF (50 mL) was heated to 140 for 16 hours. After cooled to RT the mixture was filtered and the solid was collected. The solid was dissolved in water (10 mL) and the pH value was adjusted to 34 using HCl solution (2 M) at 0. The precipitate was collected by filtration washed with water and dried to afford the title compound (2.45 g) as white solid. MS (ESI) C8H9NO3requires 167 found 168 [M+H]+.
2.45 g In N,N-dimethyl-formamide; at 140℃; for 16h; Take with<strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (D17, 3.5 g) with sodium methoxide (12.2 g) in DMF (50 mL)The mixture was heated to 140 C for 16 hours. After cooling to room temperature, the mixture was filtered and the solid was collected. The solid was dissolved in water (10 mL) and the pH was adjusted to 3 to 4 using HCl solution (2 M) at 0 C. The precipitate was collected by filtration, washed with water and dried to give the title compound (2.45 g) as a white solid
  • 10
  • [ 932705-78-7 ]
  • (S)-N-(5-chloro-2-methyl-3-((3-methylpiperazine-1-yl)methyl)phenyl)-5-fluoro-6-methylnicotinamide [ No CAS ]
  • 11
  • [ 932705-78-7 ]
  • N-(5-chloro-2-methyl-3-(((S)-3-methyl-4-((R)-tetrahydrofuran-2-carbonyl)piperazine-1-yl)methyl)phenyl)-5-fluoro-6-methylnicotinamide [ No CAS ]
  • 12
  • [ 932705-78-7 ]
  • N-(5-chloro-2-methyl-3-(((S)-3-methyl-4-((S)-tetrahydrofuran-2-carbonyl)piperazine-1-yl)methyl)phenyl)-5-fluoro-6-methylnicotinamide [ No CAS ]
  • 13
  • [ 932705-78-7 ]
  • N-(5-chloro-2-methyl-3-(((S)-3-methyl-4-((R)-tetrahydrofuran-3-carbonyl)piperazine-1-yl)methyl)phenyl)-5-fluoro-6-methylnicotinamide [ No CAS ]
  • N-(5-chloro-2-methyl-3-(((S)-3-methyl-4-((S)-tetrahydrofuran-3-carbonyl)piperazine-1-yl)methyl)phenyl)-5-fluoro-6-methylnicotinamide [ No CAS ]
  • 14
  • [ 932705-78-7 ]
  • (S)-4-(3-amino-5-chloro-2-methylbenzyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • (S)-4-(5-chloro-3-(5-fluoro-6-methylnicotinamide)-2-methylphenyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.2 g With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; for 18h; A solution of (S) -tert-butyl 4- (3-amino-5-chloro-2-methylbenzyl) -2-methylpiperazine-1-carboxylate (D30 913 mg) <strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (D17 400 mg) HATU (980 mg) and DIPEA (0.450 mL) in DCM (100 mL) was stirred at RT for 18 hours. The mixture was concentrated in vacuo to afford the title compound (1.2 g) as a red oil. MS (ESI) C25H32ClFN4O3requires 490 found 491 [M+H]+.
1.2 g 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 dichloromethane; at 20℃; for 18h; A solution of (5)-tert-butyl 4-(3 -amino-5-chloro-2-methylbenzyl)-2-methylpiperazine- 1- carboxylate (D41, 913 mg), <strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (D19, 400 mg), HATU (980 mg) andDIPEA (0.450 mL) in DCM (100 mL) was stirred at RT for 18 hours. The mixture was concentrated in vacuo to afford the title compound (1.2 g) as red oil. MS (ESI): C25H32C1FN403 requires 490; found 491 [M+H].
1.2 g With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; at 20℃; for 18h; Description 204(S)-tert-butyl 4-(5-chloro-3-(5-fluoro-6-methylnicotinamido)-2-methylbenzyl)-2-methylpiperazine-1-carboxylate (D204)NHF N.0A solution of (S)-tert-butyl 4-(3 -amino-5-chloro-2-methylbenzyl)-2-methylpiperazine-1 -carboxylate (D159, 913 mg), <strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (Dl 13, 400 mg), HATU (980 mg)and DIPEA (0.45 0 mL) in DCM (100 mL) was stirred at RT for 18 hours. The mixture wasconcentrated under vacuum to afford the title compound (1.2 g) as red oil which was used directlyfor next step without further purification. MS (ESI): C25H32C1FN4O3 requires 490, found 491[M+H].
1.2 g 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 dichloromethane; at 20℃; for 18h; Take with (S)-4-(3-amino-5-chloro-2-methylbenzyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester (D30,913 mg) <strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (D17, 400 mg),HATU (980 mg)With DIPEA (0.450 mL) in DCM (100 mL)The solution was mixed at room temperature for 18 hours.The mixture was concentrated in vacuo,To give the title compound (1.2 g) as a red oil

  • 15
  • [ 932705-78-7 ]
  • (S)-4-(3-amino-5-chloro-2-methylbenzyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • (S)-N-(5-chloro-2-methyl-3-((3-methylpiperazin-1-yl)methyl)phenyl)-5-fluoro-6-methylnicotinamide triflouroacetic acid [ No CAS ]
  • 16
  • [ 932705-78-7 ]
  • (S)-4-(5-chloro-3-(5-fluoro-6-methylnicotinamido)-2-methylbenzyl)-N-(cyclopropylmethyl)-2-methylpiperazine-1-carboxamide [ No CAS ]
  • 17
  • [ 932705-78-7 ]
  • C7H5ClFNO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 0℃; for 5h; To a mixture of <strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (D19, 44.2 mg) in DCM (10 mL) were added oxalyl dichloride (109 mg) and two drops of DMF. The reaction was stirred for 5 hours at 0C. Then the mixture was concentrated to dryness under reduced pressure. The residue was redissolved in DCM (10 mL), which was slowly added to a mixture of (5)-4-(3-amino-5-chloro-2-methylbenzyl)-N-(cyclopropylmethyl)-2-methylpiperazine-1 -carboxamide (D54, 100 mg) and DIPEA (5 mL) in DCM (10 mL) at 0C. The reaction mixture was allowed to warm to RT and stirred for 2 hours. The mixture was washed with water (15 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the crude product, which was purified by preparative HPLC to afford the title compound (24 mg) as white solid. ‘H NMR (400 MHz, CDC13):8.82 (s, 1H), 7.97 (s, 1H), 7.92 (dd, J 8.8 Hz, 1.2 Hz, 1H), 7.79 (s, 1H), 7.18 (d, J= 2.0 Hz, 1H),4.47 (t, J 5.2 Hz, 1H), 4.03 (brs, 1H), 3.64 (d, J= 12.0 Hz, 1H), 3.46-3.38 (m, 2H), 3.11-3.02 (m,311), 2.70 (d, J 11.2 Hz, 111), 2.63 (d, J= 3.2 Hz, 3H), 2.60-2.56 (m, 1H), 2.32 (s, 3H), 2.26-2.22(m, 1H), 2.05-2.00 (m, 1H), 1.22 (d, J 6.4 Hz, 3H), 0.98-0.95 (m, 1H), 0.50-0.47 (m, 2H), 0.19-0.17 (m, 2H). MS (ESI): C25H31C1FN5O2 requires 487; found 488 [M+H].
  • 18
  • [ 932705-78-7 ]
  • (S)-3-amino-5-((4-(2-cyclopropylacetyl)-3-methylpiperazin-1-yl)methyl)-4-methylbenzonitrile [ No CAS ]
  • [ 76-05-1 ]
  • (S)-N-(5-cyano-3-((4-(2-cyclopropylacetyl)-3-methylpiperazin-1-yl)methyl)-2-methylphenyl)-5-fluoro-6-methylnicotinamide trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
51 mg Example 146(S)-N-(5-cyano-3-((4-(2-cyclopropylacetyl)-3-methylpiperazin-1-yl)methyl)-2-methylphenyl)-5-fluoro-6-methylnicotinamide, Trifluoroacetic acid salt (E146)NHF N.0To a suspension of <strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (D113, 57.0 mg) in DCM (10 mL), oxalyl dichloride (0.048 mL) was added dropwise. The reaction mixture was stirred at RT under nitrogen for 2 hours. Solvent was removed by rotavap, then re-dissolved with DCM (1 mL), added to a solution of (S)-3-amino-5-((4-(2-cyclopropylacetyl)-3-methylpiperazin-1 -yl)methyl)-4-methylbenzonitrile (D174, 80 mg) and DIPEA (0.128 mL) in DCM (10 mL). The reaction mixture was stirred at RT overnight. Diluted with DCM (20 mL) then washed with brine (20 mL). DCM layer was separated, dried over MgSO4 and filtered. The filtrate was concentrated and purified by MADP to afford the title compound (51 mg) as white solid. ‘H NMR (400 MHz, MeOD-d4): 8.88 (s, 1H), 8.09 (dd, J= 9.7, 1.7 Hz, 1H), 7.86 (s, 1H), 7.85 (s, 1H), 4.59 (brs, 1H), 4.31 (brs, 2H),3.99 (brs, 1H), 3.71-3.32 (m, 2H), 3.23-2.68 (m, 3H), 2.61 (d,J 2.8 Hz, 3H), 2.53-2.15 (m, 5H),1.48-1.22 (m, 3H), 1.07-0.93 (m, 1H), 0.60-0.49 (m, 2H), 0.23-0.13 (m, 2H). ‘9F NMR (376 MHz,MeOD-d4): -77.4, -125.2. MS (ESI): C26H30FN502 requires 463; found 464 [M+H].TFA
  • 19
  • [ 932705-78-7 ]
  • (R)-4-(5-chloro-2-methyl-3-aminobenzyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • (S)-4-(5-chloro-3-(5-fluoro-6-methylnicotinamide)-2-methylphenyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.2 g 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 18h; Take with (S)-4-(3-amino-5-chloro-2-methylbenzyl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester (D30,913 mg) <strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (D17, 400 mg),HATU (980 mg)With DIPEA (0.450 mL) in DCM (100 mL)The solution was mixed at room temperature for 18 hours.The mixture was concentrated in vacuo,To give the title compound (1.2 g) as a red oil
  • 20
  • [ 932705-78-7 ]
  • [ 1211542-12-9 ]
  • 21
  • [ 932705-78-7 ]
  • (3-(3-amino-5-chloro-2-methylbenzyl)-3,8-diazabicyclo[3.2.1]octan-8-yl) tetrahydro-2H-pyran-4-yl methanone [ No CAS ]
  • Ν-(5-chloro-2-methyl-3-((8-(tetrahydro-2H-pyran-4-carbonyl)-3,8-diazabicyclo[3.2.1]octan-3-yl)methyl)phenyl)-5-fluoro-6-methyInicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
27.5% With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate; In dichloromethane; at 20℃; At room temperature, to the containing (3-(3-amino-5-chloro-2-methylbenzyl)-3,8-diazabicyclo[3.2.1]octan-8-yl) tetrahydro-2H-pyran-4-yl methanone (45.0 mg, 0 . 12 mmol) in dichloromethane solution, adding N, N - diisopropyl ethylamine (46.4 mg, 0 . 36 mmol) and 5 - fluoro -6 - methyl nicotinic acid (20.2 mg, 0 . 13 mmol), addition of HATU (114.0 mg, 0.3 mmol), after the adding of, for stirring at room temperature overnight the reaction. After the reaction is complete, the solvent is removed under reduced pressure, the residue by silica gel column chromatography (petroleum ether: ethyl acetate=5:1 - 1:1) and thick preparation plate purification to obtain white solid compound 17.0 mg, yield 27.5%.
  • 22
  • [ 932705-78-7 ]
  • (3-(3-amino-5-chloro-2-methylbenzyl)-3,8-diazabicyclo[3.2.1]octan-8-yl) tetrahydro-2H-pyran-4-yl methanone [ No CAS ]
  • Ν-(5-chloro-3-((8-(cyclopentanecarbonyl)-3-azabicyclo[3.2.1]octan-3-yl)methyl)-2-methylphenyl)-5-fluoro-6-methyInicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
20% 0 C lower, to containing <strong>[932705-78-7]5-fluoro-6-methylnicotinic acid</strong> (93.1 mg, 0.6 mmol) of dichloromethane solution (5 ml) in, dropping of a catalytic amount of DMF 2 drop, and containing oxalyl (152.4 mg, 1.2 mmol) of dichloromethane solution; after the completion of the dropping, the reaction temperature to room temperature 3 hours, decompressing to evaporate the solvent; 0 C lower, residue is dissolved in dichloromethane is used for, drop into the containing (3-(3-amino-5-chloro-2-methylbenzyl)-3,8-diazabicyclo[3.2.1]octan-8-yl) cyclopentyl methanone (150 mg, 0.4 mmol) and triethylamine (121.2 mg, 1.2 mmol) in dichloromethane solution (5 ml) in, dropped, temperature to room temperature overnight the reaction; the majority of the solvent is removed under reduced pressure, by silica gel column chromatography and thick preparation plate purification to obtain white solid compound 40.0 mg, yield 20.0%
  • 23
  • [ 932705-78-7 ]
  • 1-(3-(3-amino-5-chloro-2-methylbenzyl)-3,8-diazabicyclo[3.2.1]octan-8-yl)-2-cyclobutylethan-1-one [ No CAS ]
  • Ν-(5-chloro-3-((8-(2-cyclobutylacetyl)-3,8-diazabicyclo[3.2.1]octan-3-yl)methyl)-2-methylphenyl)-5-fluoro-6-methyInicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
24.3% With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate; In dichloromethane; at 20℃; At room temperature, to the containing 1-(3-(3-amino-5-chloro-2-methylbenzyl)-3,8-diazabicyclo[3.2.1]octan-8-yl)-2-cyclobutylethan-1-one (150.0 mg, 0 . 42 mmol) in dichloromethane solution, adding N, N - diisopropyl ethylamine (160.8 mg, 1 . 25 mmol) and 5-fluoro-6-methyl nicotinic acid (71.4 mg, 0 . 46 mmol), addition of HATU (399.2 mg, 1 . 05 mmol), after the adding of, for stirring the reaction overnight at room temperature. After the reaction is complete, the solvent is removed under reduced pressure, the residue by silica gel column chromatography (petroleum ether: ethyl acetate=5:1 - 1:1) and thick preparation plate purification to obtain white solid compound 51.0 mg, yield 24.3%.
  • 24
  • [ 932705-78-7 ]
  • C21H29N3O [ No CAS ]
  • N-(3-(8-(cyclopentanecarbonyl)-3,8-diazabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-inden-5-yl)-5-fluoro-6-methylnicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
56.9% 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 dichloromethane; at 20℃;Inert atmosphere; General procedure: Step 5a: The mixture of the crude compound 11a (1.0 eq) orcompound 11b (1.0 eq), HATU (1.5 eq), different acid (1.1 eq) andDIPEA (3.0 eq) in DCM was stirred at room temperature overnightunder N2 atmosphere. When the starting material wasconsumed completely, the mixture was washed with saturatedNaHCO3 solution and water, dried over anhydrous sodium sulfate,filtered and the filtrate was concentrated under reducedpressure to afford the crude product, which was purified bycolumn chromatography to afford the target compounds (2a, 2d,3a-3d,4a-4d, 5a, 5b, 5e-5h and 6a-6f). Enantiomers (S)-5c and(R)-5d were obtained by chiral HPLC separation of 5b.
  • 25
  • [ 932705-78-7 ]
  • C21H29N3O [ No CAS ]
  • N-(1-(8-(cyclopentanecarbonyl)-3,8-diazabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-inden-4-yl)-5-fluoro-6-methylnicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
46.5% 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 dichloromethane; at 20℃;Inert atmosphere; General procedure: Step 5a: The mixture of the crude compound 11a (1.0 eq) orcompound 11b (1.0 eq), HATU (1.5 eq), different acid (1.1 eq) andDIPEA (3.0 eq) in DCM was stirred at room temperature overnightunder N2 atmosphere. When the starting material wasconsumed completely, the mixture was washed with saturatedNaHCO3 solution and water, dried over anhydrous sodium sulfate,filtered and the filtrate was concentrated under reducedpressure to afford the crude product, which was purified bycolumn chromatography to afford the target compounds (2a, 2d,3a-3d,4a-4d, 5a, 5b, 5e-5h and 6a-6f). Enantiomers (S)-5c and(R)-5d were obtained by chiral HPLC separation of 5b.
 

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2-(Difluoromethyl)-3-fluoropyridine-5-carboxylic acid

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Chemical Structure| 402-66-4

A212213 [402-66-4]

5-Fluoronicotinic acid

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Related Parent Nucleus of
[ 932705-78-7 ]

Pyridines

Chemical Structure| 1253383-91-3

A463136 [1253383-91-3]

Methyl 5-Fluoro-6-methylnicotinate

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Chemical Structure| 1211534-44-9

A149725 [1211534-44-9]

5-Fluoro-2-methylnicotinic acid

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Chemical Structure| 917835-70-2

A683528 [917835-70-2]

5-Fluoro-6-methylnicotinaldehyde

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A856007 [1060806-01-0]

4-Fluoro-6-methylnicotinic acid

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Chemical Structure| 1806756-68-2

A836687 [1806756-68-2]

2-(Difluoromethyl)-3-fluoropyridine-5-carboxylic acid

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