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[ CAS No. 89242-09-1 ] {[proInfo.proName]}

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Chemical Structure| 89242-09-1
Chemical Structure| 89242-09-1
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Product Details of [ 89242-09-1 ]

CAS No. :89242-09-1 MDL No. :MFCD17169230
Formula : C16H10ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JBRVJPXJLHEUND-UHFFFAOYSA-N
M.W : 283.71 Pubchem ID :11000554
Synonyms :

Safety of [ 89242-09-1 ]

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

Application In Synthesis of [ 89242-09-1 ]

* 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 [ 89242-09-1 ]

[ 89242-09-1 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 89242-09-1 ]
  • [ 109960-06-7 ]
YieldReaction ConditionsOperation in experiment
With sulfuryl dichloride for 3h; Heating;
With thionyl chloride; N,N-dimethyl-formamide In dichloromethane for 0.0833333h;
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 25℃; for 2h;
  • 2
  • [ 124-09-4 ]
  • [ 89242-09-1 ]
  • [ 419535-36-7 ]
YieldReaction ConditionsOperation in experiment
65% With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 20℃; for 7h;
  • 4
  • [ 439614-61-6 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; silver nitrate In ethanol
  • 6
  • [ 849770-52-1 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
35% With aluminum (III) chloride In 1,1,2,2-tetrachloroethane at 60℃; for 1.5h; 4 A solution of 22 (12 mmol) in tetrachloroethane was added to the suspension Of AlCl3 (36 mmol) in tetrachloroethane (50 ml). The resulting mixture was heated to 60 0C for 1.5 lirs.The reaction mixture was quenched by addition of 1 M HCl (50 ml). Then, the mixture was basified by addition of NaOH (IM aqueous solution), the resulted layers were separated, and the aqueous layer was acidified by HCl (aqueous solution). This aqueous phase was extracted with CH2Cl2, dried over MgSO4 and finally the solvents were removed under reduced pressure, to give 35% yield of the desired product.1H NMR (300 MHz, CDCl3) δ (ppm): 8.71 (s, IH), 8.11 (d, J=8.1Hz, IH), 7.83 (t, J=6.6Hz,IH), 7.77-7.64 (m, 2H), 7.59 (d, J=7.5Hz, IH), 7.53-7.44 (m, 3H). 13C NMR (75 MHz, CDCl3) δ (ppm): 164.8, 157.9, 138.6, 136.7, 133.3, 131.7, 131.2, 130.6, 130.2, 130.0, 129.0,128.8, 127.8, 126.9, 122.7.MS: m/z calcd for Ci6Hi0ClNO2: 283.71; found M+: 284.
  • 7
  • [ 33966-50-6 ]
  • [ 89242-09-1 ]
  • [ 124236-61-9 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 50℃; Stage #2: SEC-BUTYLAMINE In dichloromethane Further stages.;
  • 8
  • [ 92853-34-4 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: selenium oxide / 1,2-dichloro-benzene 2: AgNO3; aq. NaOH / ethanol
Multi-step reaction with 2 steps 1: 97 percent / SeO2 / 1,2-dichloro-benzene / 6 h / 180 °C 2: 82 percent / AgNO3; NaOH / aq. ethanol / 48 h
Multi-step reaction with 3 steps 1.1: 88 percent / 2-chloroperoxybenzoic acid / CH2Cl2 2.1: (CF3CO)2O / 1,2-dichloro-benzene / 2 h / 180 °C 2.2: 68 percent / aq. NaOH / ethanol / 0.5 h 3.1: AgNO3; NaOH / aq. ethanol
Multi-step reaction with 3 steps 1: NBS; BPO / CCl4 / 5 h / Irradiation 2: AgNO3 / H2O; tetrahydrofuran / 1 h / Heating 3: AgNO3; NaOH / ethanol; H2O / 2 h / 20 °C
Multi-step reaction with 3 steps 1: 2,2'-azobis(isobutyronitrile); N-Bromosuccinimide / tetrachloromethane / 20 h / Inert atmosphere; Reflux 2: sodium periodate / N,N-dimethyl-formamide / 19 h / Inert atmosphere; Reflux 3: silver nitrate; sodium hydroxide / ethanol; water / 2 h / 20 °C / Inert atmosphere

  • 9
  • [ 53631-70-2 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aq. NaOH / CH2Cl2 2: P2O5 / 1,2-dichloro-benzene 3: selenium oxide / 1,2-dichloro-benzene 4: AgNO3; aq. NaOH / ethanol
Multi-step reaction with 5 steps 1: 90 percent / NaOH / CH2Cl2 2: 80 percent / P2O5 / 1,2-dichloro-benzene / Heating 3: NBS; BPO / CCl4 / 5 h / Irradiation 4: AgNO3 / H2O; tetrahydrofuran / 1 h / Heating 5: AgNO3; NaOH / ethanol; H2O / 2 h / 20 °C
  • 10
  • [ 609-65-4 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: aq. NaOH / CH2Cl2 2: P2O5 / 1,2-dichloro-benzene 3: selenium oxide / 1,2-dichloro-benzene 4: AgNO3; aq. NaOH / ethanol
Multi-step reaction with 5 steps 1: 90 percent / NaOH / CH2Cl2 2: 80 percent / P2O5 / 1,2-dichloro-benzene / Heating 3: NBS; BPO / CCl4 / 5 h / Irradiation 4: AgNO3 / H2O; tetrahydrofuran / 1 h / Heating 5: AgNO3; NaOH / ethanol; H2O / 2 h / 20 °C
  • 11
  • [ 89242-09-1 ]
  • [ 124236-61-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2; DMF / CH2Cl2 / 0.08 h 2: CH2Cl2
Multi-step reaction with 2 steps 1: SO2Cl2 / 3 h / Heating 2: tetrahydrofuran / 1 h / 0 °C
  • 12
  • [ 89242-09-1 ]
  • N-(1-methylethyl)-1-(2-chlorophenyl)isoquinoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2; DMF / CH2Cl2 / 0.08 h 2: CH2Cl2
Multi-step reaction with 2 steps 1: (COCl)2 / dimethylformamide; CH2Cl2 / 2 h / 25 °C 2: pyridine / tetrahydrofuran / 2 h / 25 °C
  • 13
  • [ 89242-09-1 ]
  • 1-(2-chloro-phenyl)-isoquinoline-3-carboxylic acid methylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2; DMF / CH2Cl2 / 0.08 h 2: CH2Cl2
  • 14
  • [ 89242-09-1 ]
  • 1-(2-chloro-phenyl)-isoquinoline-3-carboxylic acid ethylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2; DMF / CH2Cl2 / 0.08 h 2: CH2Cl2
  • 15
  • [ 89242-09-1 ]
  • 1-(2-chloro-phenyl)-isoquinoline-3-carboxylic acid propylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2; DMF / CH2Cl2 / 0.08 h 2: CH2Cl2
  • 16
  • [ 89242-09-1 ]
  • 1-(2-chloro-phenyl)-isoquinoline-3-carboxylic acid <i>tert</i>-butylamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2; DMF / CH2Cl2 / 0.08 h 2: CH2Cl2
  • 17
  • [ 89242-09-1 ]
  • 1-(2-chloro-phenyl)-isoquinoline-3-carboxylic acid butyl-methyl-amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2; DMF / CH2Cl2 / 0.08 h 2: CH2Cl2
  • 18
  • [ 419535-34-5 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: P2O5 / 1,2-dichloro-benzene 2: selenium oxide / 1,2-dichloro-benzene 3: AgNO3; aq. NaOH / ethanol
Multi-step reaction with 4 steps 1: 80 percent / P2O5 / 1,2-dichloro-benzene / Heating 2: NBS; BPO / CCl4 / 5 h / Irradiation 3: AgNO3 / H2O; tetrahydrofuran / 1 h / Heating 4: AgNO3; NaOH / ethanol; H2O / 2 h / 20 °C
  • 19
  • [ 89242-09-1 ]
  • N-phenyl-1-(2-chlorophenyl)isoquinoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (COCl)2 / dimethylformamide; CH2Cl2 / 2 h / 25 °C 2: pyridine / tetrahydrofuran / 2 h / 25 °C
  • 20
  • [ 89242-09-1 ]
  • N,N-dipropyl-1-(2-chlorophenyl)isoquinoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (COCl)2 / dimethylformamide; CH2Cl2 / 2 h / 25 °C 2: pyridine / tetrahydrofuran / 2 h / 25 °C
  • 21
  • [ 89242-09-1 ]
  • N,N-diallyl-1-(2-chlorophenyl)isoquinoline-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (COCl)2 / dimethylformamide; CH2Cl2 / 2 h / 25 °C 2: pyridine / tetrahydrofuran / 2 h / 25 °C
  • 22
  • [ 92874-45-8 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 65 percent / S8 / decahydronaphthalene / 8 h / Heating 2: 97 percent / SeO2 / 1,2-dichloro-benzene / 6 h / 180 °C 3: 82 percent / AgNO3; NaOH / aq. ethanol / 48 h
Multi-step reaction with 4 steps 1.1: 65 percent / S8 / decahydronaphthalene / 8 h / Heating 2.1: 88 percent / 2-chloroperoxybenzoic acid / CH2Cl2 3.1: (CF3CO)2O / 1,2-dichloro-benzene / 2 h / 180 °C 3.2: 68 percent / aq. NaOH / ethanol / 0.5 h 4.1: AgNO3; NaOH / aq. ethanol
  • 23
  • [ 69454-42-8 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 82 percent / POBr3; K2CO3 / acetonitrile / 1.5 h / Heating 2: 90 percent / K2PO4 / Pd(PPh3)4 / dimethylformamide / 5 h / 80 °C 3: 95 percent / NaOH / aq. ethanol / 1 h / Heating
  • 24
  • [ 93010-73-2 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: POCl3 / acetonitrile / 3 h / Heating 2: 65 percent / S8 / decahydronaphthalene / 8 h / Heating 3: 97 percent / SeO2 / 1,2-dichloro-benzene / 6 h / 180 °C 4: 82 percent / AgNO3; NaOH / aq. ethanol / 48 h
Multi-step reaction with 5 steps 1.1: POCl3 / acetonitrile / 3 h / Heating 2.1: 65 percent / S8 / decahydronaphthalene / 8 h / Heating 3.1: 88 percent / 2-chloroperoxybenzoic acid / CH2Cl2 4.1: (CF3CO)2O / 1,2-dichloro-benzene / 2 h / 180 °C 4.2: 68 percent / aq. NaOH / ethanol / 0.5 h 5.1: AgNO3; NaOH / aq. ethanol
  • 25
  • [ 609-65-4 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine / acetonitrile / 2 h 2: POCl3 / acetonitrile / 3 h / Heating 3: 65 percent / S8 / decahydronaphthalene / 8 h / Heating 4: 97 percent / SeO2 / 1,2-dichloro-benzene / 6 h / 180 °C 5: 82 percent / AgNO3; NaOH / aq. ethanol / 48 h
Multi-step reaction with 6 steps 1.1: triethylamine / acetonitrile / 2 h 2.1: POCl3 / acetonitrile / 3 h / Heating 3.1: 65 percent / S8 / decahydronaphthalene / 8 h / Heating 4.1: 88 percent / 2-chloroperoxybenzoic acid / CH2Cl2 5.1: (CF3CO)2O / 1,2-dichloro-benzene / 2 h / 180 °C 5.2: 68 percent / aq. NaOH / ethanol / 0.5 h 6.1: AgNO3; NaOH / aq. ethanol
  • 26
  • [ 63586-82-3 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 93 percent / H2SO4 / 8 h / Heating 2: 72 percent / 10percent Pd/C / diphenyl ether / Heating 3: 82 percent / POBr3; K2CO3 / acetonitrile / 1.5 h / Heating 4: 90 percent / K2PO4 / Pd(PPh3)4 / dimethylformamide / 5 h / 80 °C 5: 95 percent / NaOH / aq. ethanol / 1 h / Heating
  • 27
  • [ 23364-15-0 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 72 percent / 10percent Pd/C / diphenyl ether / Heating 2: 82 percent / POBr3; K2CO3 / acetonitrile / 1.5 h / Heating 3: 90 percent / K2PO4 / Pd(PPh3)4 / dimethylformamide / 5 h / 80 °C 4: 95 percent / NaOH / aq. ethanol / 1 h / Heating
  • 28
  • 2-amino-1-phenylpropane [ No CAS ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: triethylamine / acetonitrile / 2 h 2: POCl3 / acetonitrile / 3 h / Heating 3: 65 percent / S8 / decahydronaphthalene / 8 h / Heating 4: 97 percent / SeO2 / 1,2-dichloro-benzene / 6 h / 180 °C 5: 82 percent / AgNO3; NaOH / aq. ethanol / 48 h
Multi-step reaction with 6 steps 1.1: triethylamine / acetonitrile / 2 h 2.1: POCl3 / acetonitrile / 3 h / Heating 3.1: 65 percent / S8 / decahydronaphthalene / 8 h / Heating 4.1: 88 percent / 2-chloroperoxybenzoic acid / CH2Cl2 5.1: (CF3CO)2O / 1,2-dichloro-benzene / 2 h / 180 °C 5.2: 68 percent / aq. NaOH / ethanol / 0.5 h 6.1: AgNO3; NaOH / aq. ethanol
  • 29
  • [ 439614-62-7 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / K2PO4 / Pd(PPh3)4 / dimethylformamide / 5 h / 80 °C 2: 95 percent / NaOH / aq. ethanol / 1 h / Heating
  • 30
  • [ 439614-64-9 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: (CF3CO)2O / 1,2-dichloro-benzene / 2 h / 180 °C 1.2: 68 percent / aq. NaOH / ethanol / 0.5 h 2.1: AgNO3; NaOH / aq. ethanol
  • 31
  • [ 89242-09-1 ]
  • 1-(2-methylene-6-methylquinoline)-4-10-bis(methylene-phosphonic acid)-7-(methylene-1-(2-chlorophenyl)-N-hexyl-3-isoquinoline carboxamide)-1,4,7,10-tetraazacyclododecane [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 65 percent / BOP; Et3N / dimethylformamide / 7 h / 20 °C 2: 46 percent / TSTU; triethylamine / H2O; dioxane; dimethylformamide / 96 h / 20 °C
  • 32
  • [ 501084-68-0 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: AgNO3 / H2O; tetrahydrofuran / 1 h / Heating 2: AgNO3; NaOH / ethanol; H2O / 2 h / 20 °C
  • 33
  • [ 89242-09-1 ]
  • [ 109960-11-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SO2Cl2 / 3 h / Heating 2: NaHCO3 / CHCl3; H2O / 1 h / Ambient temperature 3: iodotrimethylsilane / acetonitrile / 0.17 h / Ambient temperature
  • 34
  • [ 89242-09-1 ]
  • [ 110012-97-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SO2Cl2 / 3 h / Heating 2: NaHCO3 / CHCl3; H2O / 1 h / Ambient temperature 3: iodotrimethylsilane / acetonitrile / 0.17 h / Ambient temperature
  • 35
  • [ 89242-09-1 ]
  • [ 110012-99-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SO2Cl2 / 3 h / Heating 2: NaHCO3 / CHCl3; H2O / 1 h / Ambient temperature 3: iodotrimethylsilane / acetonitrile / 0.17 h / Ambient temperature
  • 36
  • [ 89242-09-1 ]
  • [ 109960-10-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SO2Cl2 / 3 h / Heating 2: NaHCO3 / CHCl3; H2O / 1 h / Ambient temperature
  • 37
  • [ 89242-09-1 ]
  • [ 110012-95-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SO2Cl2 / 3 h / Heating 2: NaHCO3 / CHCl3; H2O / 1 h / Ambient temperature
  • 38
  • [ 89242-09-1 ]
  • [ 110012-96-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SO2Cl2 / 3 h / Heating 2: NaHCO3 / CHCl3; H2O / 1 h / Ambient temperature
  • 39
  • [ 110-89-4 ]
  • [ 541-41-3 ]
  • [ 89242-09-1 ]
  • 1-[[1-(2-chlorophenyl)-3-isoquinolyl]carbonyl]piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In chloroform 13 1-[[1-(2-chlorophenyl) 3-isoquinolyl]carbonyl]piperidine EXAMPLE 13 1-[[1-(2-chlorophenyl) 3-isoquinolyl]carbonyl]piperidine Operations are carried out as for Example 7, starting with 1.42 g of 1-(2-chlorophenyl) isoquinoline 3-carboxylic acid, 0.58 g of triethylamine, 0.62 g of ethyl chloroformate and 0.55 g of piperidine in 50 ml of chloroform. 1.2 g of 1-[[1-(2-chlorophenyl) 3-isoquinolyl]carbonyl]piperidine, melting at 161° C. is obtained.
  • 40
  • [ 541-41-3 ]
  • [ 774152-11-3 ]
  • [ 89242-09-1 ]
  • [ 85532-75-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; triethylamine In toluene 44 N-methyl N-1-(S)-methyl propyl) 1-(2-chloro phenyl) isoquinoline 3-carboxamide EXAMPLE 44 N-methyl N-1-(S)-methyl propyl) 1-(2-chloro phenyl) isoquinoline 3-carboxamide Operations are carried out as for Example 7, starting from 1.7 g of 1-(2-chloro phenyl) isoquinoline 3-carboxylic acid, 2.1 g of triethylamine, 0.75 g of ethyl chloroformate and 0.96 g of N-methyl 2(S)-butanamine, HCl in 60 ml of toluene. After chromatography and recrystallization in cyclohexane, 0.5 g of N-methyl N-(1-(S)-methyl propyl) 1-(2-chlorophenyl) isoquinoline 3-carboxamide melting at 134° C. is obtained. αD27 =+53.7° (0.5% in CHCl3).
  • 41
  • [ 89242-09-1 ]
  • [ 107-15-3 ]
  • [ 1009737-69-2 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 1-(2-chlorophenyl)-3-isoquinoline carboxylic acid With oxalyl dichloride In dichloromethane at 20℃; for 2h; Stage #2: ethylenediamine With pyridine In tetrahydrofuran at 20℃; Cooling with ice; 1-(2-Chloro-phenyl)-isoquinoline-3-carboxylic acid 23 (2.12 mmol) was suspended in dry CH2Cl2 (20 ml) and oxalyl chloride (4.24 mmol) was added followed by 2 drops of dimethyl formamide. The mixture was stirred at r.t. for 2 hrs. The solvent was removed under reduced pressure and traces of oxalyl chloride were removed by the addition and subsequent evaporation of toluene (2×3 ml). The residue was dissolved in dry THF (30 ml), cooled with an ice bath and pyridine (2.12 mmol) with the corresponding diamine (1.06 mmol) were added to the reaction mixture. The reaction mixture was stirred at r.t. for additional 3 hrs. Water (50 ml) was added to the reaction, followed by extraction of aqueous layer with ethyl acetate, the combined organic layers were dried over MgSO4 and solvents were removed by reduced pressure. The resulting crude product was purified by alumina (neutral) chromatography.; The general procedure VI was applied for the preparation of 24a in 75% yield. Purification was performed with (1:2) EtOAc:dichloromethane.1H NMR (300 MHz, CDCl3) δ (ppm): 8.55 (s, 2H), 8.48 (m, 1H), 7.96 (d, J=7.8 Hz, 2H), 7.71 (t, J=7.8 Hz, 3H), 7.69 (d, J=8.4 Hz, 2H), 7.60 (d, J=8.4 Hz, 2H), 7.53 (d, J=8.4 Hz, 2H), 7.47-7.44 (m, 2H), 7.40-7.29 (m, 4H), 3.77-3.66 (m, 4H).MS: m/z calcd for C34H24Cl2N4O2: 591.49; found M+: 591.3.
  • 42
  • [ 40547-06-6 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
35% Stage #1: 4-benzylidene-2-(2-chloro-phenyl)-4<i>H</i>-oxazol-5-one With aluminum (III) chloride In 1,1,2,2-tetrachloroethane at 60℃; for 1.5h; Stage #2: With hydrogenchloride In water; 1,1,2,2-tetrachloroethane Stage #3: With sodium hydroxide In water; 1,1,2,2-tetrachloroethane A solution of 22 (12 mmol) in tetrachloroethane was added to the suspension of AlCl3 (36 mmol) in tetrachloroethane (50 ml). The resulting mixture was heated to 60° C. for 1.5 hrs. The reaction mixture was quenched by addition of 1 M HCl (50 ml). Then, the mixture was basified by addition of NaOH (1M aqueous solution), the resulted layers were separated, and the aqueous layer was acidified by HCl (aqueous solution). This aqueous phase was extracted with CH2Cl2, dried over MgSO4 and finally the solvents were removed under reduced pressure, to give 35% yield of the desired product.1H NMR(300 MHz, CDCl3) δ (ppm): 8.71 (s, 1H), 8.11 (d, J=8.1 Hz, 1H), 7.83 (t, J=6.6 Hz, 1H), 7.77-7.64 (m, 2H), 7.59 (d, J=7.5 Hz, 1H), 7.53-7.44 (m, 3H). 13C NMR (75 MHz, CDCl3) δ (ppm): 164.8, 157.9, 138.6, 136.7, 133.3, 131.7, 131.2, 130.6, 130.2, 130.0, 129.0, 128.8, 127.8, 126.9, 122.7.MS: m/z calcd for C16H10ClNO2: 283.71; found M+: 284.
  • 43
  • [ 88192-19-2 ]
  • [ 89242-09-1 ]
  • [ 1456688-36-0 ]
YieldReaction ConditionsOperation in experiment
99% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h; Compound 10 Compound 10: Under argon, carboxylic acid 9 (19 mg, 0.067 mmol) and amine 8 (35 mg, 0.35 mmol) were mixed in anhydrous DMF (1 mL), diisopropylethylamine (37 μA, 27 mg, 0.21 mmol). HATU (51 mg, 0.134 mmol) was dissolved separately in anhydrous DMF (0.5 mL) and then introduced via syringe to the reaction. After 30 minutes, the reaction was concentrated in vacuo. The oil was diluted in methylene chloride and washed with 0.1 M HCl (3×) then water (2×). The methylene chloride layer was dried over sodium sulfate, filtered, and concentrated in vacuo. A colorless solid was obtained (24 mg, 99%). ESI-MS (m/z) for C19H16ClN5O (exact mass 365.01): [M+H]+ calc. 366.1, obs. 366.2.
  • 44
  • [ 85532-75-8 ]
  • [ 89242-09-1 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogenchloride; water at 110℃; for 24h; Sealed tube; Compound 9 Compound 9: PK 1195 (25 mg, 0.071 mmol) and 6 N HCl (1 mL) was added to a thick walled glass pressure flask. The flask was then sealed and heated at 110° C. for 24 hours. The reaction was concentrated in vacuo, dissolved in a solution of water/acetonitrile (1:1), frozen and lyophilized. A white powder was obtained (19 mg, 97%). 1H-NMR (500 MHz, CDCl3): 8.46 (s, 1H), 8.11 (d, J=8.2 Hz, 1H), 7.85 (t, J=7.4 Hz, 1H), 7.41-7.68 (m, 6H). ESI-MS (m/z) for C16H10ClNO2 (exact mass 283.04): [M+H]+ calc. 284.0, obs. 284.2.
  • 45
  • [ 89242-09-1 ]
  • PK [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h 2: copper(II) sulfate; sodium L-ascorbate / water; ethanol / 0.5 h / 35 °C
  • 46
  • [ 89242-09-1 ]
  • PK [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h 2: copper(II) sulfate; sodium L-ascorbate / water; ethanol / 0.5 h / 35 °C 3: trifluoroacetic acid; ethane-1,2-dithiol / 0.17 h
  • 47
  • [ 89242-09-1 ]
  • PK [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h 2: copper(II) sulfate; sodium L-ascorbate / water; ethanol / 0.5 h / 35 °C
  • 48
  • [ 89242-09-1 ]
  • PK [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h 2: copper(II) sulfate; sodium L-ascorbate / water; ethanol / 0.5 h / 35 °C 3: trifluoroacetic acid / 0.17 h
  • 49
  • [ 134179-38-7 ]
  • [ 89242-09-1 ]
  • [ 1456688-40-6 ]
YieldReaction ConditionsOperation in experiment
96% With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide for 0.5h; Compound 13 Compound 13: Under argon, carboxylic acid 9 (14 mg, 0.05 mmol) and 11-azido-3,6,9-trioxaundecan-1-amine (16 mg, 0.075 mmol) were mixed in anhydrous DMF (1 mL) in the presence of diisopropylethylamine (44 ul, 32 mg, 0.25 mmol). HATU (23 mg, 0.06 mmol) was dissolved separately in anhydrous DMF (1 mL) and then introduced via syringe to the reaction. After 30 minutes, the reaction was concentrated in vacuo. The oil was diluted in methylene chloride and washed with 0.1 M HCl (3×) then water (2×). The methylene chloride layer was concentrated in vacuo. The resulting oil was diluted in water/acetonitrile (1:1), frozen and lyophilized. A colorless solid was obtained (23 mg, 96%). ESI-MS (m/z) for C24H26ClN5O4 (exact mass 483.17): [M+H]+ calc. 484.17, obs. 484.3.
  • 50
  • TBDPS butyl sec-butylamine [ No CAS ]
  • [ 89242-09-1 ]
  • C40H45ClN2O2Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
67.7% Stage #1: 1-(2-chlorophenyl)isoquinoline-3-carboxylic acid With thionyl chloride In dichloromethane Reflux; Stage #2: TBDPS butyl sec-butylamine In dichloromethane at 0 - 5℃; 1 Synthesis of compound represented by formula (2): 100mg of 1-(2-chlorophenyl)-3-isoquinolinecarboxylic acid as shown in formula (1) in Figure 1,Dissolve in 5ml of dichloromethane, add 0.16ml of thionyl chloride as a chloroacylating reagent, and react under reflux for 0-3h.After rotating the solvent, dissolve the concentrate in 5ml of dichloromethane, add 203mg of the compound represented by the formula (a) in Figure 1 and 170mg of base at 0-5°C, keep the temperature and continue the reaction for 1-3h, add 30ml of water for extraction The reaction was quenched, and 30ml of dichloromethane was added for extraction, the organic phase was washed with saturated brine, and separated by column chromatography (mobile phase: n-hexane: ethyl acetate=4:1) to obtain the compound represented by formula (2) in Figure 1 155mg, the yield is 67.7%
Same Skeleton Products
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