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Chemical Structure| 80567-00-6 Chemical Structure| 80567-00-6

Structure of 80567-00-6

Chemical Structure| 80567-00-6

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Product Details of [ 80567-00-6 ]

CAS No. :80567-00-6
Formula : C6H14ClNO
M.W : 151.63
SMILES Code : CC1OC(C)CNC1.[H]Cl
MDL No. :MFCD28099212
InChI Key :SFEUYYPUMLXCLF-UHFFFAOYSA-N
Pubchem ID :19374754

Safety of [ 80567-00-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 80567-00-6 ]

* 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 [ 80567-00-6 ]

[ 80567-00-6 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 941-98-0 ]
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • 3-(2,6-dimethyl-morpholin-4-yl)-1-naphthalen-1-yl-propan-1-one [ No CAS ]
  • 2
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 133914-37-1 ]
  • [ 24223-60-7 ]
  • 3
  • [ 50-00-0 ]
  • [ 99-91-2 ]
  • [ 80567-00-6 ]
  • 1-(4-chloro-phenyl)-3-(2,6-dimethyl-morpholin-4-yl)-propan-1-one [ No CAS ]
  • 4
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 98-86-2 ]
  • 3-(2,6-dimethyl-morpholin-4-yl)-1-phenyl-propan-1-one [ No CAS ]
  • 5
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 122-00-9 ]
  • 3-(2,6-dimethyl-morpholin-4-yl)-1-<i>p</i>-tolyl-propan-1-one [ No CAS ]
  • 6
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 93-55-0 ]
  • [ 82418-91-5 ]
  • 7
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 100-19-6 ]
  • 3-(2,6-dimethyl-morpholin-4-yl)-1-(4-nitro-phenyl)-propan-1-one [ No CAS ]
  • 8
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 67-64-1 ]
  • [ 97382-78-0 ]
  • 9
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 122-57-6 ]
  • 5-(2,6-dimethyl-morpholin-4-yl)-1-phenyl-pent-1-en-3-one [ No CAS ]
  • 10
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 100-06-1 ]
  • 3-(2,6-dimethyl-morpholin-4-yl)-1-(4-methoxy-phenyl)-propan-1-one [ No CAS ]
  • 11
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 121-89-1 ]
  • 3-(2,6-dimethyl-morpholin-4-yl)-1-(3-nitro-phenyl)-propan-1-one [ No CAS ]
  • 12
  • [ 80567-00-6 ]
  • diacetyl<<7,8-difluoro-9,1-<(methylimino)methano>-5-oxo-5H-thiazolo<3,2-a>quinolin-4-yl>carbonyl>borane [ No CAS ]
  • 5-(2,6-Dimethyl-morpholin-4-yl)-6-fluoro-4-methyl-8-oxo-3,4-dihydro-8H-1-thia-4,9b-diaza-cyclopenta[cd]phenalene-9-carboxylic acid [ No CAS ]
  • 13
  • [ 80567-00-6 ]
  • [ 72036-33-0 ]
  • 4-(2,6-dimethylmorpholin-4-yl)-1-oxaspiro[4.5]dec-3-en-2-one [ No CAS ]
  • 14
  • sodium cyanoboron hydride [ No CAS ]
  • [ 147118-22-7 ]
  • [ 325477-93-8 ]
  • [ 80567-00-6 ]
  • 4-[3-(3-benzoylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In methanol; EXAMPLE 1 Synthesis of 4-[3-(3-benzoylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine (Compound No.1). 0.7 g of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong>, a mixture of cis-trans isomers, are dissolved in 8 cc of methanol. 0.069 g of potassium hydroxide and 1 g of 3-(3-benzoylphenyl)-2-methylpropanal are added. After 15 minutes a solution of 0.084 g of sodium cyanoboron hydride in 1 cc of methanol are added dropwise and after a further 30 minutes 0.27 g of potassium hydrate in powder form are added. The mixture is filtered on celite and the solvent evaporated at reduced pressure. The raw product is purified by silica gel chromatography, with hexane/ethyl acetate=9/1 as eluant, to obtain 0.8 g of compound 1, cis isomer.
  • 15
  • [ 80567-00-6 ]
  • [ 1078-19-9 ]
  • 6-methoxy-2-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalen-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With paraformaldehyde;hydrogenchloride; In ethanol; EXAMPLE 1 This Example illustrates the preparation of 6-methoxy-2-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalene (compound No. 11 of Table 1). 6-Methoxy-1,2,3,4-tetrahydronaphthalen-1-one (17.6 g, 0.1 mol), <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> (15.1 g, 0.1 mol), and paraformaldehyde (6.0 g, 0.2 mol) were refluxed together in ethanol (50 ml) with concentrated hydrochloric acid (0.25 ml) as a catalyst for 3 hours. The reaction was cooled and poured into water containing concentrated hydrochloric acid (5 ml) and extracted with ether (200 ml). The aqueous solution was cooled in ice and neutralised with sodium hydroxide solution (10%) then extracted with ether (2*200 ml) dried over magnesium sulphate and evaporated under reduced pressure to give a residue which was recrystallized from petrol (60-80) to give 6-methoxy-2-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalen-1-one a white crystalline solid (10 g, 33% yield) melting at 110 C.
  • 16
  • [ 51015-37-3 ]
  • [ 80567-00-6 ]
  • 6-tert-butyl-2-cis-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalen-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
39% With paraformaldehyde;hydrogenchloride; In ethanol; water; EXAMPLE 3 This Example illustrates the preparation of 7-tert-butyl-3-cis-(2,6-dimethylmorpholinomethyl)-1,2-dihydronaphthalene (Compound No. 2 in Table I). 2,6-Dimethylmorpholine hydrochloride (12.1 g, 0.08 mol), 6-tert-butyl-1,2,3,4-tetrahydronaphthalen-1-one (8.1 g, 0.04 mol) and paraformaldehyde (2.4 g, 0.08 mol) were refluxed together in ethanol (150 ml) with concentrated hydrochloric acid (1 ml) as a catalyst for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water then extracted with diethyl ether. The resulting aqueous solution was neutralised with sodium bicarbonate and extracted with diethyl ether (2*200 ml); the ethereal extracts were dried over anhydrous magnesium sulphate and concentrated under reduced pressure to give an orange oil. This oil was purified by hplc (silica eluted with ethyl acetate/petroleum ether 1:1) to give 6-tert-butyl-2-cis-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalen-1-one (5.1 g, 39%).
39% With paraformaldehyde;hydrogenchloride; In ethanol; water; EXAMPLE 2 This Example illustrates the preparation of 6-tert-butyl-2-cis-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalene (Compound No. 21 in Table I). 2,6-Dimethylmorpholine hydrochloride (12.1 g, 0.08 mol), 6-tert-butyl-1,2,3,4-tetrahydronaphthalen-1-one (8.1 g, 0.04 mol), and paraformaldehyde (2.4 g, 0.08 mol) were refluxed together in ethanol (150 ml) with concentrated hydrochloric acid (1 ml) as a catalyst for 16 hours. The reaction mixture was concentrated under reduced pressure and the residue dissolved in water then extracted with diethyl ether. The resulting aqueous solution was neutralised with sodium bicarbonate and extracted with diethyl ether (2*200 ml); the ethereal extracts were dried over anhydrous magnesium sulphate and concentrated under reduced pressure to give an orange oil. This oil was purified by hplc (silica eluted with ethyl acetate/petroleum ether 1:1) to give 6-tert-butyl-2-cis-(2,6-dimethylmorpholinomethyl)-1,2,3,4-tetrahydronaphthalen-1-one (5.1 g, 39%).
  • 17
  • [ 147118-22-7 ]
  • [ 25895-60-7 ]
  • [ 80567-00-6 ]
  • 4-[3-(3-benzoylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium hydroxide; In methanol; EXAMPLE 2 Synthesis of 4-[3-(3-benzoylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine (Compound No. 1). 0.7 g of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong>, a mixture of cis-trans isomers, are dissolved in 8 ml of methanol, whereafter 0.069 g of potassium hydroxide and 1 g of 3-(3-benzoylphenyl)-2-methylpropanal are added. After 15 minutes a solution of 0.084 g of sodium cyano borohydride in 1 ml of methanol is added dropwise and after a further 30 minutes 0.27 g of potassium hydroxide in powder form are added. The mixture is filtered on celite and the solvent evaporated at reduced pressure. The crude product is purified by silica gel chromatography, with hexane/ethyl acetate = 9/1 as eluent, to obtain 0.8 g of compound 1, cis isomer.
  • 18
  • [ 914935-69-6 ]
  • [ 80567-00-6 ]
  • 5-bromo-2-(2,6-dimethyl-morpholin-4-yl)-3,4-difluoro-benzaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; for 24h;Heating / reflux;Product distribution / selectivity; Step 3: 5-Bromo-2-(2,6-dimethyl-morpholin-4-yl)-3,4-difluoro-benzaldehyde. To a solution of 5-bromo-2,3,4-trifluoro-benzaldehyde (11.5g, 48mmol) in dry acetonitrile (18OmL) was added Et3N (16.7mL, 120mmol) and 2,6-dimethylmorpholine, HCI Salt(8.3g, 53mmol). The reaction mixture was refluxed for 24 h. The solution was allowed to cool to room temperature and then poured into a saturated solution of NaHCO,,. The phases were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO . and concentrated to give an orange oil (15 g). Slurry of the crude in heptane yielded 11.92g of a yellow solid. 1 H-NMR (500 MHz, CDCI3) d 10.36 (s, 1H), 7.82 (dd, 1 H), 4.19 (m, 2H), 3.3 (d, 2H), 2.97 (dd,2H),1.30 (d, 6H).
  • 19
  • [ 61636-30-4 ]
  • [ 80567-00-6 ]
YieldReaction ConditionsOperation in experiment
Step 2: 2,6-DimethyI-morpholine, HCI Salt. 4-Benzyl-2R,6R-(trans)-dimethyl- morpholine (15g, 73 mmol) was charged to an autoclave and MeOH (800 mL) added. Pd/C (3.5 g) was added and the mixture was stirred at room temperature overnight under 3.5 bars of pressure of H2. The mixture was then filtered through celite followed by the addition of HCI 2M in Et2O (47 mL,1.3 eq, 95 mmol). This filtrate was then concentrated to give the 8.3 g of the moφholine salt. 1 H-NMR (500 MHz, CDCI3) d 4.26 (m, 2H), 3.25(m, 2H), 2.94 (m, 2H), 1.39 (m, 6H).
  • 20
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 115665-92-4 ]
  • 5-(2,6-dimethylmorpholinyl)-1-(4-trifluoromethylphenyl)-1-penten-3-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
33.16% 0.165g (1.1mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.3g (10mmol) of paraformaldehyde were dissolved in anhydrous ethanol (5ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 1hr. After the solid was dissolved, 0.214g (1.0mmol) of 4-(4-trifluoromethylphenyl)-3-buten-2-one (prepared as described in preparation 16) was added to the above reaction mixture. The solution was further refluxed and stirred for 12hr. After cooling with ice-water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol and dried to give 0.125g of white crystals, yield: 33.16 %, mp: 203-205C . 1HNMRδppm (DMSO-d6): 1.09(d, 6H, J=6.6Hz, 2CH3-CH), 2.47-2.68(m, 6H, 3NCH2), 3.33-3.43(m, 2H, COCH2), 3.85(q, 2H, J=6.6Hz, 2CH3-CH), 7.04(d, 1H, J=16.2Hz, =CHCO), 7.759(d, 1H, J=16.2Hz, CH=), 7.819(d, 2H, J=8.4Hz, ArHAA'), 7.955(d, 2H, J=8.4Hz, ArHBB')o FAB-MS (m/z): 342.2(M++1 ), 274.2(M+-F3C+1), 128.4(M+-213).
  • 21
  • [ 50-00-0 ]
  • [ 22292-71-3 ]
  • [ 80567-00-6 ]
  • 5-(2,6-dimethylmorpholinyl)-1-(3-ethoxy-4-hydroxyphenyl)-1-penten-3-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
25.3% 0.5g (3.3mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.9g (30mmol) of paraformaldehyde were dissolved in anhydrous ethanol (15ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 1hr. After the solid was dissolved, 0.619g (3.0mmol) of 4-(3-ethoxy-4-hydroxyphenyl)-3-buten-2-one (prepared as described in preparation 5) was added to the above reaction mixture. The solution was further refluxed and stirred for 9hr. After cooling with cold water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol - methanol and dried to give 0.281g of white crystals, yield 25.3 %, mp: 198-201C. 1HNMRδppm (DMSO-d6): 1.10(d, 6H, J=6.6Hz, 2xCHCH3), 1.29-1.33 (t, 3H, J=7.2Hz, OCH2CH3), 2.47-2.61(m, 6H, 2NCH2), 2.62-2.69 (t, 2H, COCH2), 3.25-3.46(q, 2H, J=7.2Hz, OCH2CH3), 3.87(q, 1H, OH, D2O exchange), 3.95(q, 2H, J=6.6Hz, 2xCHCH3), 6.73(d, 1H, J=16.2Hz, =CHCO), 6.84(d, 1H, J=8.1Hz, ArH), 7.15(q, 1H, J=8.1Hz, J=1.5Hz, ArH), 7.29(s, 1H, ArH), 7.59(d, 1H, J=16.2Hz, CH=). FAB-MS (m/z): 334.3(M++1).
  • 22
  • [ 50-00-0 ]
  • [ 943596-70-1 ]
  • [ 80567-00-6 ]
  • 5-(2,6-dimethylmorpholinyl)-1-(3-methoxy-4-ethoxyphenyl)-1-penten-3-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
19.5% 0.303g (2.0mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.6g (20mmol) of paraformaldehyde were dissolved in anhydrous ethanol (5ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 1hr. After the solid was dissolved, 0.44g (2.0mmol) of 4-(3-methoxy-4-ethoxyphenyl)-3-buten-2-one (prepared as described in preparation 6) was added to the above reaction mixture. The solution was further refluxed and stirred for 11hr. TLC showed the reaction was completed. After cooling with cold water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol - methanol and dried to give 0.15g of white crystals, yield: 19.5 %, mp: 191-194C. 1HNMRδppm (DMSO-d6): 1.06-1.12(d, 6H, J=6.6Hz, 2xCHCH3), 1.29-1.34(t, 3H, J=7.2Hz, OCH2CH3), 2.02-3.20(m, 6H, 3NCH2), 3.24-3.46(q, 2H, J=7.2Hz, OCH2CH3), 3.79(s, 3H, OCH3), 4.05(q, 2H, J=6.6Hz, 2xCHCH3), 6.61(d, 1H, J=16.2Hz, =CHCO), 6.98(d, 1H, J=8.4Hz, ArH), 7.25(d, 1H, J=8.4Hz, ArH), 7.32(d, 1H, J=8.4Hz, ArH), 7.64(d, 1H, J=16.2Hz, CH=). MS (m/z): 347(M+, 42), 232(M+-115, 94), 190((M+-115-14, 10).
  • 23
  • [ 50-00-0 ]
  • (E)-4-(3-hydroxy-4-methoxyphenyl)but-3-en-2-one [ No CAS ]
  • [ 80567-00-6 ]
  • 5-(2,6-dimethylmorpholinyl)-1-(3-hydroxy-4-methoxyphenyl)-1-penten-3-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
36.6% 0.303g (2.0mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.4g (13mmol) of paraformaldehyde were dissolved in anhydrous ethanol (5ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 2.0hr. After the solid was dissolved, 0.384g (2.0mmol) of 4-(3-hydroxy-4-methoxyphenyl)-3-buten-2-one (preparedas described in preparation 20) was added to the above reaction mixture. The solution was further refluxed and stirred for 15hr. TLC showed the reaction was completed. After cooling with cold water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol and dried to give 0.26g of white crystals, yield: 36.6 %, mp: 194-196C. 1HNMRδppm (DMSO-d6): 1.09(d, 6H, J =6.6Hz, 2xCHCH3), 2.47-2.68 (m, 6H, 3NCH2), 3.24-3.46(t, 2H, COCH2), 3.95(q, 2H, J=6.6Hz, 2xCHCH3), 6.61(d, 1H, J=16.2Hz, =CHCO), 6.98(d, 1H, J=8.4Hz, ArH), 7.14(d, 2H, J=8.4Hz, ArH), 7.57(d, 1H, J=16.2Hz, CH=). MS (m/z): 319(M+, 40), 204(M+-115, 35), 190(M+-115-14, 10).
  • 24
  • [ 50-00-0 ]
  • [ 30626-03-0 ]
  • [ 80567-00-6 ]
  • 5-(2,6-dimethylmorpholinyl)-1-(4-chlorophenyl)-1-penten-3-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
53.8% 0.303g (2.0mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.4g (13mmol) of paraformaldehyde were dissolved in anhydrous ethanol (5ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 2hr. After the solid was dissolved, 0.36g (2.0mmol) of 4-(4-chlorophenyl)-3-buten-2-one (prepared as described in preparation 1) was added to the above reaction mixture. The solution was further refluxed and stirred for 13hr. TLC showed the reaction was completed. After cooling with ice-water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol and dried to give 0.37g of white crystals, yield: 53.8 % , mp: 218-220C. 1HNMRδppm (DMSO-d6): 1.09(d, 6H, J=6.6Hz, 2 x CHCH3), 2.47-2.68 (m, 6H, 3NCH2), 3.24-3.46(t, 2H, COCH2), 3.95(q, 2H, J=6.6Hz, 2 x CHCH3), 6.92(d, 1H, J=16.2Hz, =CHCO), 7.49(d, 2H, J=8.4Hz, ArHAA'), 7.69(d, 1H, J=16.2Hz, CH=), 7.79(d, 2H, J=8.4Hz, ArHBB'). MS (m/z): 307(M+, 20), 192(M+-114-H, 24), 165(M+-142, 60).
  • 25
  • [ 50-00-0 ]
  • [ 80567-00-6 ]
  • [ 22214-31-9 ]
  • 5-(2,6-dimethylmorpholinyl)-1-(3,4-methylenedioxyphenyl)-1-penten-3-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
65.2% 0.30g (2.0mmol) of <strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> and 0.15g (5mmol) of paraformaldehyde were dissolved in anhydrous ethanol (10ml). The pH value of the solution was adjusted to pH =1.5-2.0 with concentrated hydrochloric acid and the reaction mixture was refluxed and stirred for 2hr. After the solid was dissolved, 0.38g (2.0mmol) of 4-(3,4-methylenedioxyphenyl)-3-buten-2-one (prepared as described in preparation 15) was added to the above reaction mixture. The solution was further refluxed and stirred for 11hr. After cooling with cold water bath, the precipitated pale yellow solid was collected by filtration and then recrystallized from anhydrous ethanol - methanol and dried to give 0.46g of white crystals, yield: 65.2 %, mp: 178-181C. 1HNMRδppm (DMSO-d6): 1.11(d, 6H, J=6.6Hz, 2 x CHCH3), 2.47-2.68 (m, 6H, 3NCH2), 3.26-3.46(t, 2H, COCH2), 3.89(q, 2H, J=6.6Hz, 2 x CHCH3), 6.08(s, 2H, OCH2O), 6.77(d, 1H, J=16.2Hz, =CHCO), 6.98(d, 1H, J=8.4Hz,ArH), 7.20(dd, 1H, J=8.4Hz, J=1.5Hz, ArH), 7.39(d, 1H, J=1.5Hz, ArH), 7.61(d, 1H, J=16.2Hz, CH=). MS (m/z): 317(M+, 45), 302(M+-15, 3), 272(M+-45, 5), 202(M+-115, 90). Anal. Cald. for C22H31N2O5Cl: C:61.10%, H:6.78%, N: 3.96%; Found: C: 61.23%, H:6.59%, N:3.98%.
  • 26
  • 1-(6-[4-ethyl-5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]amino}pyrimidin-4-yl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid [ No CAS ]
  • [ 80567-00-6 ]
  • (±)-[syn-2,6-dimethylmorpholin-4-yl][1-(6-[4-ethyl-5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]amino}pyrimidin-4-yl)-3,5-dimethyl-1H-pyrazol-4-yl]methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% 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; at 20.0℃; A mixture of 1-(6-[4-ethyl-5-(4-fluorophenyl)-1-methyl-1H-pyrazol-3-yl]amino}pyrimidin-4-yl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid (72.6 mg, 167 μιηο), cis-<strong>[80567-00-6]2,6-dimethylmorpholine hydrochloride</strong> (1 : 1) (50.6 mg, 333 μιηο), (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate) (139 mg, 367 μιηο) and N,N-Diisopropylethylamine (120 μ, 700 μηιο) was stirred overnight at room temperature. The mixture was directly purified by preparative HPLC (method: column: Reprosil C18; 10 μηι; 125x30 mm / flow: 50 ml/min / eluent: A = water (0.01% formic acid), B = acetonitrile / gradient: 0.00-5.00 min = 10% B, 6.50 min = 20% B, 17.0-19.75 min = 100% B, 19.75-23.00 min = 90% B) to yield 49.8 mg (56% yield) of the desired product. LC-MS (method 10): Rt = 1.99 min; MS (ESIpos): m/z = 533 [M+H]+1H-NMR (400 MHz, DMSO-d6) δ [ppm]: -0.008 (4.17), 0.008 (2.94), 0.146 (0.41), 0.871 (3.38), 0.890 (7.62), 0.909 (3.51), 1.073 (3.40), 1.091 (5.53), 1.108 (3.43), 2.165 (5.64), 2.286 (0.76), 2.304 (2.17), 2.323 (2.61), 2.366 (0.41), 2.523 (2.02), 2.670 (0.70), 2.710 (0.49), 3.357 (0.82), 3.375 (2.25), 3.392 (2.26), 3.410 (0.95), 3.478 (0.89), 3.651 (16.00), 7.359 (2.06), 7.381 (6.32), 7.403 (2.69), 7.499 (2.50), 7.512 (2.88), 7.520 (2.17), 7.534 (1.85), 8.477 (3.59), 9.433 (2.07).
 

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Related Parent Nucleus of
[ 80567-00-6 ]

Morpholines

Chemical Structure| 168038-14-0

A339625 [168038-14-0]

(R)-2-Methylmorpholine hydrochloride

Similarity: 1.00

Chemical Structure| 276252-76-7

A267107 [276252-76-7]

(2S,6S)-2,6-Dimethylmorpholine hydrochloride

Similarity: 1.00

Chemical Structure| N/A

A729984 [N/A]

(2R,6R)-2,6-Dimethylmorpholine hydrochloride

Similarity: 1.00

Chemical Structure| 1147108-99-3

A502948 [1147108-99-3]

(S)-2-Methylmorpholine hydrochloride

Similarity: 1.00

Chemical Structure| 1147108-99-3

A502948 [1147108-99-3]

(S)-2-Methylmorpholine hydrochloride

Similarity: 1.00