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[ CAS No. 173436-02-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 173436-02-7
Chemical Structure| 173436-02-7
Chemical Structure| 173436-02-7
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Product Details of [ 173436-02-7 ]

CAS No. :173436-02-7 MDL No. :MFCD02094527
Formula : C12H25NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :YJHJMTNYNBJHIZ-UHFFFAOYSA-N
M.W : 231.33 Pubchem ID :10353840
Synonyms :

Calculated chemistry of [ 173436-02-7 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 10
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 65.47
TPSA : 58.56 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.07
Log Po/w (XLOGP3) : 2.21
Log Po/w (WLOGP) : 2.45
Log Po/w (MLOGP) : 1.83
Log Po/w (SILICOS-IT) : 2.06
Consensus Log Po/w : 2.33

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.01
Solubility : 2.28 mg/ml ; 0.00985 mol/l
Class : Soluble
Log S (Ali) : -3.07
Solubility : 0.195 mg/ml ; 0.000843 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.1
Solubility : 0.185 mg/ml ; 0.0008 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.35

Safety of [ 173436-02-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 173436-02-7 ]

* 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 [ 173436-02-7 ]

[ 173436-02-7 ] Synthesis Path-Downstream   1~38

  • 1
  • [ 60142-89-4 ]
  • [ 173436-02-7 ]
YieldReaction ConditionsOperation in experiment
A solution of 7- [ (tert-butoxycarbonyl) amino] heptanoic acid (25g) in THF (1500ml) was cooled to 0C under nitrogen atmosphere. Borane-dimethyl sulfide complex (29ml) was added to the solution. The mixture was stirred at 0C for 2h. IN-aqueous solution of sodium hydroxide (326ml) was added to the mixture at 5-10C over lh. The mixture was stirred at room temperature for lh. Then THF was removed in vacuo. The remaining aqueous solution was extracted with Et20. The combined organic layer was washed with brine. The organic layer was dried over magnesium sulfate, and evaporated in vacuo to give crude colorless oil (24. 1g). The crude oil was dissolved in THF (500ml) under nitrogen atmosphere. Triphenylphosphine (34.7g) and carbon tetrabromide (43. 9g) were added to the solution at room temperature, and the mixture was stirred at room temperature for 13h. The reaction mixture was filtered, and the filtrate was evapolated in vacuo. The residue was purified with silica gel chromatography (AcOEt/hexane =1/10 to 1/4 elution) to give tert-butyl (7-bromoheptyl) carbamate (22.6g). mp. 48-49C
  • 2
  • [ 173436-02-7 ]
  • [ 142356-34-1 ]
YieldReaction ConditionsOperation in experiment
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran; acetonitrile for 24h;
With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 13h; 18.1 A solution of 7- [ (tert-butoxycarbonyl) amino] heptanoic acid (25g) in THF (1500ml) was cooled to 0°C under nitrogen atmosphere. Borane-dimethyl sulfide complex (29ml) was added to the solution. The mixture was stirred at 0°C for 2h. IN-aqueous solution of sodium hydroxide (326ml) was added to the mixture at 5-10°C over lh. The mixture was stirred at room temperature for lh. Then THF was removed in vacuo. The remaining aqueous solution was extracted with Et20. The combined organic layer was washed with brine. The organic layer was dried over magnesium sulfate, and evaporated in vacuo to give crude colorless oil (24. 1g). The crude oil was dissolved in THF (500ml) under nitrogen atmosphere. Triphenylphosphine (34.7g) and carbon tetrabromide (43. 9g) were added to the solution at room temperature, and the mixture was stirred at room temperature for 13h. The reaction mixture was filtered, and the filtrate was evapolated in vacuo. The residue was purified with silica gel chromatography (AcOEt/hexane =1/10 to 1/4 elution) to give tert-butyl (7-bromoheptyl) carbamate (22.6g). mp. 48-49C
  • 4
  • [ 173436-02-7 ]
  • [ 344744-50-9 ]
  • [7-(2-ethylsulfanyl-8-methyl-4-oxo-4<i>H</i>-chromen-7-yloxy)-heptyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate In dichloromethane; toluene for 18h;
  • 5
  • [ 173436-02-7 ]
  • 7-(7-amino-heptyloxy)-8-methyl-2-morpholin-4-yl-chromen-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: DEAD; PPh3 / toluene; CH2Cl2 / 18 h 2: AcOH / 75 °C 3: TFA / CH2Cl2 / 1 h / 20 °C
  • 6
  • [ 173436-02-7 ]
  • [7-(8-methyl-2-morpholin-4-yl-4-oxo-4<i>H</i>-chromen-7-yloxy)-heptyl]-carbamic acid <i>tert</i>-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: DEAD; PPh3 / toluene; CH2Cl2 / 18 h 2: AcOH / 75 °C
  • 7
  • [ 173436-02-7 ]
  • LY7Me-GM [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: DEAD; PPh3 / toluene; CH2Cl2 / 18 h 2: AcOH / 75 °C 3: TFA / CH2Cl2 / 1 h / 20 °C 4: TEA / dimethylformamide
  • 8
  • [ 173436-02-7 ]
  • [ 176435-76-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: TFA / CH2Cl2 / 1 h 2: DCCI, HOBt, DIPEA / dimethylformamide / 15 h 3: 359 mg / Et3N, DMAP / CH2Cl2 / 15 h 4: 69 percent / NaN3 / dimethylformamide / a) 60 deg C, 3 h, b) RT, 15 h 5: 76 percent / H2 / Lindlar catalyst / ethanol / 6 h / 30 °C / 2068.6 Torr
  • 9
  • [ 173436-02-7 ]
  • [ 173436-03-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: TFA / CH2Cl2 / 1 h 2: DCCI, HOBt, DIPEA / dimethylformamide / 15 h 3: 359 mg / Et3N, DMAP / CH2Cl2 / 15 h 4: 69 percent / NaN3 / dimethylformamide / a) 60 deg C, 3 h, b) RT, 15 h
  • 10
  • [ 173436-02-7 ]
  • {(S)-1-[(R)-1-(7-Methanesulfonylamino-heptylcarbamoyl)-1-methyl-2-phenyl-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: TFA / CH2Cl2 / 1 h 2: DCCI, HOBt, DIPEA / dimethylformamide / 15 h 3: 359 mg / Et3N, DMAP / CH2Cl2 / 15 h 4: 69 percent / NaN3 / dimethylformamide / a) 60 deg C, 3 h, b) RT, 15 h 5: 76 percent / H2 / Lindlar catalyst / ethanol / 6 h / 30 °C / 2068.6 Torr 6: 21 percent / pyridine / CH2Cl2 / 15 h
  • 11
  • [ 173436-02-7 ]
  • [ 173436-08-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: TFA / CH2Cl2 / 1 h 2: DCCI, HOBt, DIPEA / dimethylformamide / 15 h 3: 359 mg / Et3N, DMAP / CH2Cl2 / 15 h
  • 12
  • [ 173436-02-7 ]
  • {(S)-1-[1-(7-Hydroxy-heptylcarbamoyl)-1-methyl-2-phenyl-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 1 h 2: DCCI, HOBt, DIPEA / dimethylformamide / 15 h
  • 14
  • [ 173436-02-7 ]
  • 2-(S)-<<(benzyloxy)carbonyl>amino>-3-<4-<(7-N-aminoheptyl)oxy>phenyl>propionic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Ph3P, CBr4 / tetrahydrofuran; acetonitrile / 24 h 2: 1.) NaH / 1.) DMF, 1 h, 2.) DMF, 24 h 3: 20 percent / HCl (gas) / ethyl acetate
  • 15
  • [ 173436-02-7 ]
  • [ 142355-74-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Ph3P, CBr4 / tetrahydrofuran; acetonitrile / 24 h 2: 1.) NaH / 1.) DMF, 1 h, 2.) DMF, 24 h
  • 16
  • [ 10160-24-4 ]
  • [ 173436-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide; tetrabutylammomium bromide / toluene / 16 h / 20 °C / Reflux 2: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 3: tetrahydrofuran / 20 °C
Multi-step reaction with 2 steps 1.1: N,N-dimethyl-formamide / 3 h / 120 °C 1.2: Reflux 2.1: potassium carbonate / methanol; water / 4 h / 20 °C
  • 17
  • [ 629-30-1 ]
  • [ 173436-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: hydrogen bromide / water; toluene / 43 h / Reflux 2: sodium azide; tetrabutylammomium bromide / toluene / 16 h / 20 °C / Reflux 3: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 4: tetrahydrofuran / 20 °C
Multi-step reaction with 3 steps 1: triethylamine; dmap / dichloromethane / 16 h / 10 °C / Inert atmosphere 2: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere 3: hydrogen; palladium on activated carbon / ethyl acetate / 16 h / 25 °C / 2585.81 Torr
  • 18
  • [ 19243-04-0 ]
  • [ 24424-99-5 ]
  • [ 173436-02-7 ]
YieldReaction ConditionsOperation in experiment
99% In tetrahydrofuran at 20℃;
92% In dichloromethane at 0 - 20℃; for 16h; General Procedure 1 Boc protection of primary amines General procedure: A reaction vessel containing a stirring bar was charged with the appropriate amine dissolved in CH2Cl2 (0.2 M). The solution was cooled to 0 °C and di-tert-butyl dicarbonate (1.5 equivalents) was added to the reaction vessel. The reaction was stirred at room temperature for 16 h.
92% In dichloromethane at 0 - 20℃; for 16h; General Procedure 1 Boc protection of primary amines General procedure: A reaction vessel containing a stirring bar was charged with the appropriate amine dissolved in CH2Cl2 (0.2 M). The solution was cooled to 0 °C and di-tert-butyl dicarbonate (1.5 equivalents) was added to the reaction vessel. The reaction was stirred at room temperature for 16 h.
81% With potassium carbonate In methanol; water at 20℃; for 4h;

  • 19
  • [ 57395-45-6 ]
  • [ 173436-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / methanol / 20 °C / 760.05 Torr 2: tetrahydrofuran / 20 °C
  • 20
  • [ 173436-02-7 ]
  • C12H24(18)FNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate; triethylamine / dichloromethane / 72 h / 20 °C 2: potassium carbonate; [2.2.2]cryptande; [18F]fluoride ion, cyclotron produced, NCA / acetonitrile / 0.17 h / 90 °C / Sealed tube
  • 21
  • [ 173436-02-7 ]
  • C7H16(18)FN [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate; triethylamine / dichloromethane / 72 h / 20 °C 2: potassium carbonate; [2.2.2]cryptande; [18F]fluoride ion, cyclotron produced, NCA / acetonitrile / 0.17 h / 90 °C / Sealed tube 3: trifluoroacetic acid / acetonitrile / 0.17 h / 20 °C
  • 22
  • [ 173436-02-7 ]
  • C14H19(18)FN2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate; triethylamine / dichloromethane / 72 h / 20 °C 2: potassium carbonate; [2.2.2]cryptande; [18F]fluoride ion, cyclotron produced, NCA / acetonitrile / 0.17 h / 90 °C / Sealed tube 3: trifluoroacetic acid / acetonitrile / 0.17 h / 20 °C 4: triethylamine / acetonitrile / 0.12 h / 90 °C
  • 23
  • [ 173436-02-7 ]
  • 13-methyl-5,8,13,13a-tetrahydro-6H-isoquinolino[1,2-b]quinazolin-10-yl (7-[18F]fluoroheptyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: potassium carbonate; triethylamine / dichloromethane / 72 h / 20 °C 2: potassium carbonate; [2.2.2]cryptande; [18F]fluoride ion, cyclotron produced, NCA / acetonitrile / 0.17 h / 90 °C / Sealed tube 3: trifluoroacetic acid / acetonitrile / 0.17 h / 20 °C 4: triethylamine / acetonitrile / 0.12 h / 90 °C 5: triethylamine / acetonitrile / 0.12 h / 90 °C
  • 24
  • [ 98-59-9 ]
  • [ 173436-02-7 ]
  • 7-(tert-butoxycarbonylamino)heptyl-p-tolyl sulfate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With potassium carbonate; triethylamine In dichloromethane at 20℃; for 72h;
  • 25
  • [ 201230-82-2 ]
  • [ 86536-92-7 ]
  • [ 173436-02-7 ]
YieldReaction ConditionsOperation in experiment
53% With sodium tetrahydroborate; dimanganese decacarbonyl In 1,4-dioxane; tert-Amyl alcohol at 50℃; for 18h; Inert atmosphere; Sealed tube;
  • 26
  • [ 24424-99-5 ]
  • [ 57395-45-6 ]
  • [ 173436-02-7 ]
YieldReaction ConditionsOperation in experiment
67% With palladium on activated carbon; hydrogen In ethyl acetate at 25℃; for 16h; 3 Step 3 - Tert-butyl N-(7-hydroxyheptyl)carbamate A mixture of 7-azidoheptan-1-ol (1.92 g, 12.2 mmol), Pd/C (400 mg, 10% wt) and Boc2O (2.93 g, 13.4 mmol) in EA (40 mL) was stirred at 25 °C for 16 hours under H2 (50 Psi). On completion, the mixture was filtered and the cake was washed with EA (10 mL). The filtrate and washing were combined and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound (1.90 g, 67% yield) as light yellow gum.1H NMR (400 MHz, DMSO-d6) d 6.74 (s, 1H), 4.31 (t, J = 5.2 Hz, 1H), 3.41 - 3.33 (m, 2H), 2.89 - 2.84 (m, 2H), 1.44 - 1.39 (m, 2H), 1.37 (s, 9H), 1.34 (m, 2H), 1.24 (m, 6H).
  • 27
  • [ 124-63-0 ]
  • [ 173436-02-7 ]
  • 7-(tert-butoxycarbonylamino)heptyl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine In dichloromethane at 0 - 10℃; for 2h; Inert atmosphere; 4 Step 4 - 7-(Tert-butoxycarbonylamino)heptyl methanesulfonate To a solution of tert-butyl N-(7-hydroxyheptyl)carbamate (1.90 g, 8.21 mmol) and TEA (1.66 g, 16.4 mmol) in DCM (30 mL) was added MsCl (1.41 g, 12.3 mmol) at 0 °C. The mixture was stirred at 0- 10 °C for 2 hours. On completion, the reaction was quenched with sat. aq. NH4Cl (10 mL) and the mixture was partitioned. The organic layer was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (2.54 g, 100% yield) as light yellow solid.1H NMR (400 MHz, DMSO-d6) d 6.75 (t, J = 4.8 Hz, 1H), 4.17 (t, J = 6.4 Hz, 2H), 3.15 (s, 3H), 2.91 - 2.86 (m, 2H), 1.69 - 1.60 (m, 2H), 1.37 (s, 9H), 1.36 - 1.16 (m, 8H).
  • 28
  • [ 311805-13-7 ]
  • [ 173436-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide; tetra-(n-butyl)ammonium iodide / N,N-dimethyl-formamide / 16 h / 60 °C / Inert atmosphere 2: hydrogen; palladium on activated carbon / ethyl acetate / 16 h / 25 °C / 2585.81 Torr
  • 29
  • [ 173436-02-7 ]
  • tert-butyl N-[7-(methylamino)heptyl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 2 h / 0 - 10 °C / Inert atmosphere 2: ethanol / 16 h / 70 °C / Inert atmosphere
  • 30
  • [ 173436-02-7 ]
  • tert-butyl N-[4-[4-[[1-[4-[[(7-(tert-butoxycarbonylamino)heptyl)methylamino]methyl]cyclohexyl]-3-(difluoromethyl)pyrazol-4-yl]carbamoyl]oxazol-2-yl]-2-pyridyl]-N-(cyclopropylmethyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 2 h / 0 - 10 °C / Inert atmosphere 2.1: ethanol / 16 h / 70 °C / Inert atmosphere 3.1: triethylamine; acetic acid / tetrahydrofuran; d<SUB>7</SUB>-N,N-dimethylformamide / 0.5 h / 0 °C / pH 5 / Inert atmosphere 3.2: 1.5 h / 0 °C / Inert atmosphere
  • 31
  • [ 173436-02-7 ]
  • N-[1-[4-[[7-aminoheptyl(methyl)amino]methyl]cyclohexyl]-3-(difluoromethyl)pyrazol-4-yl]-2-[2-(cyclopropylmethylamino)-4-pyridyl]oxazole-4-carboxamide trifluoroacetic acid salt [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triethylamine / dichloromethane / 2 h / 0 - 10 °C / Inert atmosphere 2.1: ethanol / 16 h / 70 °C / Inert atmosphere 3.1: triethylamine; acetic acid / tetrahydrofuran; d<SUB>7</SUB>-N,N-dimethylformamide / 0.5 h / 0 °C / pH 5 / Inert atmosphere 3.2: 1.5 h / 0 °C / Inert atmosphere 4.1: dichloromethane / 1 h / 15 °C / Inert atmosphere
  • 32
  • [ 173436-02-7 ]
  • N-tert-butoxycarbonyl-7-iodo-1-aminoheptane [ No CAS ]
YieldReaction ConditionsOperation in experiment
906 mg With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 1.5h; 6 To a solution of triphenylphosphine (768 mg, 2.922 mmol) in DCM (10 mL) were added imidazole (198 mg, 2.922 mmol) and diiodine (742 mg, 2.922 mmol). After 10 min, a solution of tert-butyl (7-hydroxyheptyl)carbamate (450 mg, crude) in DCM (2 mL) was added dropwise. After 1.5 h, the mixture was filtered and the filtrate was washed with sodium thiosulfate (aq.). The organic phase was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified using silica gel eluting with EtOAc in PE from 0 to 20% to give tert-butyl (7-iodoheptyl)carbamate (906 mg) in 91% yield. MS (ESI) m/z: 342.1 [M+H]
  • 33
  • [ 173436-02-7 ]
  • tert-butyl (7-(2-(4-(4-acryloylpiperazin-1-yl)-6-chloro-8-fluoroquinazolin-7-yl)-3-fluorophenoxy)heptyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 1.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C
  • 34
  • [ 173436-02-7 ]
  • 1-(4-(7-(2-((7-aminoheptyl)oxy)-6-fluorophenyl)-6-chloro-8-fluoroquinazolin-4-yl)piperazin-1-yl)prop-2-en-1-one trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 1.5 h / 20 °C 2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 3: dichloromethane / 1 h / 20 °C
  • 35
  • [ 173436-02-7 ]
  • 1-(7-(2-(4-(4-acryloylpiperazin-1-yl)-6-chloro-8-fluoroquinazolin-7-yl)-3-fluorophenoxy)heptyl)-3-((5-(2,6-dioxopiperidin-3-yl)-4-oxo-5,6-dihydro-4H-thieno[3,4-c]pyrrol-1-yl)methyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 1.5 h / 20 °C 2.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 3.1: dichloromethane / 1 h / 20 °C 4.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 4.2: 1 h / 0 - 20 °C 4.3: 1 h / 20 °C
  • 36
  • [ 929-17-9 ]
  • [ 173436-02-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride 2: dichloromethane / 16 h / 0 - 20 °C
  • 37
  • [ 173436-02-7 ]
  • tert-butyl (E)-9-((tert-butoxycarbonyl)amino)non-2-enoate [ No CAS ]
  • tert-butyl 9-((tert-butoxycarbonyl)amino)non-2-enoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h 2: dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere
  • 38
  • [ 173436-02-7 ]
  • [ 133728-25-3 ]
YieldReaction ConditionsOperation in experiment
With oxalyl dichloride; dimethyl sulfoxide In dichloromethane for 0.75h; tert-Butyl (E)-9-((tert-butoxycarbonyl)amino)non-2-enoate (S43) To a reaction vessel containing a stirring bar was added CH2Cl2 (20 cm3). The solution was cooled to -78 °C and oxalyl chloride (630 mg, 5 mmol) was then added to the solution. DMSO (781 mg, 10 mmol) was then added to the solution dropwise at -78 and the reaction stirred for 15 minutes. After 15 minutes, S42 (560 mg, 2.4 mmol) dissolved in a solution of CH2Cl2 (5 cm3) was added to the reaction mixture and stirred for 45 minutes. The reaction was then quenched with triethylamine (1.45 g, 14 mmol) and the solution brought to room temperature. The reaction solution was then diluted with water (10 cm3) and extracted with CH2Cl2 (2 x 30 cm3). The combined organic extracts were washed further with brine (10 cm3), dried over MgSO4, filtered and the filtrate concentrated in vacuo at 20 . The resulting oil was used without further purification. General procedure 3 was followed, using S4 (900 mg, 2.4 mmol) in CH2Cl2 (20 cm3). The resulting oil was purified via flash chromatography on silica gel (100% Hexane to 20% EtOAc). The desired product was obtained as a colourless oil in 83% yield, over two steps (652 g, 7:1 trans:cis) δH (400 MHz, CDCl3): 1.31-1.35 (4H, m), 1.45 (18H, s), 1.45-1.46 (4H, m), 2.13-2.18 (2H, app. q), 3.09-3.10 (2H, app. q), 4.48 (1H, br s), 5.70-5.74 (1H, d, J 15.6), 6.80-6.88 (1H, dt, J 15.6, 7.0) δC (100 MHz, CDCl3): 26.5, 27.8, 28.1, 28.4, 28.8, 30.0, 32.1, 40.5, 80.2 (q), 81.9 (q), 123.0, 147.9, 153.8 (C=O), 166.1 (C=O) nmax (film)/cm-1: 980, 1159, 1552, 1355, 1710, 2931, 3321 HRMS (m/z -ESI): Found: 350.2302 [M+Na]+ C18H33NNaO4; Requires: 350.2302
With oxalyl dichloride; dimethyl sulfoxide In dichloromethane for 0.75h; tert-Butyl (E)-9-((tert-butoxycarbonyl)amino)non-2-enoate (S43) To a reaction vessel containing a stirring bar was added CH2Cl2 (20 cm3). The solution was cooled to -78 °C and oxalyl chloride (630 mg, 5 mmol) was then added to the solution. DMSO (781 mg, 10 mmol) was then added to the solution dropwise at -78 and the reaction stirred for 15 minutes. After 15 minutes, S42 (560 mg, 2.4 mmol) dissolved in a solution of CH2Cl2 (5 cm3) was added to the reaction mixture and stirred for 45 minutes. The reaction was then quenched with triethylamine (1.45 g, 14 mmol) and the solution brought to room temperature. The reaction solution was then diluted with water (10 cm3) and extracted with CH2Cl2 (2 x 30 cm3). The combined organic extracts were washed further with brine (10 cm3), dried over MgSO4, filtered and the filtrate concentrated in vacuo at 20 . The resulting oil was used without further purification. General procedure 3 was followed, using S4 (900 mg, 2.4 mmol) in CH2Cl2 (20 cm3). The resulting oil was purified via flash chromatography on silica gel (100% Hexane to 20% EtOAc). The desired product was obtained as a colourless oil in 83% yield, over two steps (652 g, 7:1 trans:cis) δH (400 MHz, CDCl3): 1.31-1.35 (4H, m), 1.45 (18H, s), 1.45-1.46 (4H, m), 2.13-2.18 (2H, app. q), 3.09-3.10 (2H, app. q), 4.48 (1H, br s), 5.70-5.74 (1H, d, J 15.6), 6.80-6.88 (1H, dt, J 15.6, 7.0) δC (100 MHz, CDCl3): 26.5, 27.8, 28.1, 28.4, 28.8, 30.0, 32.1, 40.5, 80.2 (q), 81.9 (q), 123.0, 147.9, 153.8 (C=O), 166.1 (C=O) nmax (film)/cm-1: 980, 1159, 1552, 1355, 1710, 2931, 3321 HRMS (m/z -ESI): Found: 350.2302 [M+Na]+ C18H33NNaO4; Requires: 350.2302
Same Skeleton Products
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