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[ CAS No. 479622-36-1 ] {[proInfo.proName]}

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Chemical Structure| 479622-36-1
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Quality Control of [ 479622-36-1 ]

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Product Details of [ 479622-36-1 ]

CAS No. :479622-36-1 MDL No. :MFCD08059333
Formula : C10H18INO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DNUFVBGZKFHSDQ-UHFFFAOYSA-N
M.W : 311.16 Pubchem ID :46737825
Synonyms :

Calculated chemistry of [ 479622-36-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 69.56
TPSA : 29.54 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) : -6.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.98
Log Po/w (XLOGP3) : 2.6
Log Po/w (WLOGP) : 2.3
Log Po/w (MLOGP) : 2.29
Log Po/w (SILICOS-IT) : 2.09
Consensus Log Po/w : 2.45

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.14
Solubility : 0.224 mg/ml ; 0.000719 mol/l
Class : Soluble
Log S (Ali) : -2.87
Solubility : 0.42 mg/ml ; 0.00135 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.33
Solubility : 1.45 mg/ml ; 0.00465 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.92

Safety of [ 479622-36-1 ]

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

Application In Synthesis of [ 479622-36-1 ]

* 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 [ 479622-36-1 ]

[ 479622-36-1 ] Synthesis Path-Downstream   1~49

  • 1
  • [ 82938-50-9 ]
  • [ 479622-36-1 ]
  • [ 479622-21-4 ]
YieldReaction ConditionsOperation in experiment
With lithium diisopropyl amide In tetrahydrofuran
Stage #1: (4S)-N-tert-butyldimethylsilylazetidin-2-one-4-carboxylic acid With lithium diisopropyl amide In tetrahydrofuran at -20 - -10℃; for 0.5h; Stage #2: 3-iodomethylpyrrolidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran for 8h; 10.1.D To a solution of diisopropylamine (0.68 mL, 4.82 mmol) in 5 mL of THF was added BuLi (1.6 M, 2.88 mL, 4.62 mmol) at -15° C. The solution was cooled to -78° C. and stirred for 20 minutes. A solution of β-lactam 44 (from Example 4) (500 mg, 2.20 mmol) in 2 mL of THF was added dropwise. The solution was warmed to -20° C. to -10° C. and stirred at this temperature for 30 minutes. Then a solution of compound e (1.03 g, 3.30 mmol) in 3 mL of THF was added. The reaction mixture was stirred for 8 hours and then quenched with 5% KHSO4 until PH=3-4. The aqueous solution was extracted with EtOAc (3×20 mL). Organic extracts were combined, washed with brine, and concentrated. The residue was taken up with 60 mL of ether and the solution was extracted with sat. NaHCO3 solution (3×20 mL). The basic aqueous layers were washed with ether (20 mL), cooled to 0° C., acidified with 10% KHSO4 until PH=3-4, extracted with EtOAc (3×20 mL). The extracts were washed with brine, dried over MgSO4, and concentrated to provide compound f as a colorless oil (0.60 g). MS 413.3 (M+H)+.
  • 2
  • [ 114214-69-6 ]
  • [ 479622-36-1 ]
YieldReaction ConditionsOperation in experiment
With 1H-imidazole; iodine; triphenylphosphine; In dichloromethane; at 20℃; for 2h; Triphenyl phosphine (2.89 g, 11.00 mmol) was dissolved in 25 mL of CH2Cl2. Imidazole (0.75 g, 11.00 mmol) was added followed by iodine (2.79 g, 11.00 mmol). The solution of compound d in 5 mL of CH2Cl2 was slowly added. The reaction mixture was stirred for at room temperature for 2 hours, and then filtered. The filtrate was concentrated. The residue was triturated with EtOAc, The EtOAc solution was washed with 5% NaS2O3 and brine, dried over MgSO4, and concentrated. The residue was purified by silica gel chromatography (ethyl acetate:hexane=6:1, Rf=0.25) to afford compound e (2.30 g) as a colorless oil. MS: 312.1 (M+H)+.
  • 7
  • [ 479622-36-1 ]
  • (2S,3R)-4-Oxo-3-pyrrolidin-3-ylmethyl-azetidine-2-carboxylic acid benzyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: LDA / tetrahydrofuran 2: TBAF / tetrahydrofuran 3: NaHCO3 / dimethylformamide 4: TFA / CH2Cl2
  • 8
  • [ 479622-36-1 ]
  • 4-[(2S,3R)-3-(1-Carbamimidoyl-pyrrolidin-3-ylmethyl)-2-carboxy-4-oxo-azetidine-1-carbonyl]-piperazine-1-carboxylic acid 1-isopropyl-2-methyl-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: LDA / tetrahydrofuran 2: TBAF / tetrahydrofuran 3: NaHCO3 / dimethylformamide 4: TFA / CH2Cl2 5: Hg(OAc)2; TEA / dimethylformamide 6: TEA; DMAP / dimethylformamide 7: H2; aq. HCl / Pd/C / dioxane
Multi-step reaction with 7 steps 1: LDA / tetrahydrofuran 2: TBAF / tetrahydrofuran 3: NaHCO3 / dimethylformamide 4: TFA / CH2Cl2 5: TEA / dimethylformamide 6: TEA; DMAP / dimethylformamide 7: H2; aq. HCl / Pd/C / dioxane
  • 10
  • [ 479622-36-1 ]
  • 4-[(2S,3R)-2-Benzyloxycarbonyl-3-(1-{benzyloxycarbonylamino-[(E)-benzyloxycarbonylimino]-methyl}-pyrrolidin-3-ylmethyl)-4-oxo-azetidine-1-carbonyl]-piperazine-1-carboxylic acid 1-isopropyl-2-methyl-propyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: LDA / tetrahydrofuran 2: TBAF / tetrahydrofuran 3: NaHCO3 / dimethylformamide 4: TFA / CH2Cl2 5: Hg(OAc)2; TEA / dimethylformamide 6: TEA; DMAP / dimethylformamide
Multi-step reaction with 6 steps 1: LDA / tetrahydrofuran 2: TBAF / tetrahydrofuran 3: NaHCO3 / dimethylformamide 4: TFA / CH2Cl2 5: TEA / dimethylformamide 6: TEA; DMAP / dimethylformamide
  • 11
  • [ 86-93-1 ]
  • [ 479622-36-1 ]
  • [ 1163127-86-3 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-Phenyl-1H-tetrazole-5-thiol With potassium hydroxide In ethanol for 1h; Heating / reflux; Stage #2: 3-iodomethylpyrrolidine-1-carboxylic acid tert-butyl ester In ethanol for 3h; Heating / reflux; 9.9.i To a solution of 1 -phenyl- lH-tetrazole-5-thiol (5.92 g, 33 mmol) in EtOH (8O mL) was added KOη (2.1 g, 38 mmol) and the mixture was heated at reflux for I h. (i?5)-3-iodomethyl-pyrrolidine-l-carboxylic acid tert-butyl ester (9.O g, 29 mmol) was added and refluxing was continued for 3 h. Water (70 mL) was added and the majority of EtOH was removed under reduced pressure. The residue was extracted with EA and the org. layer was washed with water and brine, dried over MgSO4 and concentrated. To the crude sulfide thus obtained in EtOH (200 mL) was added ammonium molybdate (7.0 g, 0.2 eq) and 30% H2O2 (15 mL) and the mixture was heated to 65 0C and stirred at that temperature for 3 h. Water (500 mL) was added and the majority of EtOH was removed under reduced pressure. The residue was extracted with EA. The org. layer was washed with 10% Na2S2O3, water and brine, dried over MgSO4 and concentrated under reduced pressure to afford the title intermediate as a pale yellow oil (9.48 g, 85% yield). MS (ESI, m/z): 394.3 [M+H+].
  • 12
  • [ 479622-36-1 ]
  • [ 1163127-87-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: potassium hydroxide / ethanol / 1 h / Heating / reflux 1.2: 3 h / Heating / reflux 2.1: ammonium molibdate; dihydrogen peroxide / ethanol; water / 3 h / 65 °C
  • 13
  • [ 479622-36-1 ]
  • [ 1163127-94-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: potassium hydroxide / ethanol / 1 h / Heating / reflux 1.2: 3 h / Heating / reflux 2.1: ammonium molibdate; dihydrogen peroxide / ethanol; water / 3 h / 65 °C 3.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 1.75 h / -78 - 20 °C 4.1: AD-mix-β; methanesulfonamide; water / <i>tert</i>-butyl alcohol / 20 °C 5.1: toluene-4-sulfonic acid / tetrahydrofuran / 36 h / 20 °C 6.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C 7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h
  • 14
  • [ 479622-36-1 ]
  • [ 1163127-88-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium hydroxide / ethanol / 1 h / Heating / reflux 1.2: 3 h / Heating / reflux 2.1: ammonium molibdate; dihydrogen peroxide / ethanol; water / 3 h / 65 °C 3.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 1.75 h / -78 - 20 °C
  • 15
  • [ 479622-36-1 ]
  • [ 1163127-90-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium hydroxide / ethanol / 1 h / Heating / reflux 1.2: 3 h / Heating / reflux 2.1: ammonium molibdate; dihydrogen peroxide / ethanol; water / 3 h / 65 °C 3.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 1.75 h / -78 - 20 °C 4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 1 h
  • 16
  • [ 479622-36-1 ]
  • [ 1163127-92-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium hydroxide / ethanol / 1 h / Heating / reflux 1.2: 3 h / Heating / reflux 2.1: ammonium molibdate; dihydrogen peroxide / ethanol; water / 3 h / 65 °C 3.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 1.75 h / -78 - 20 °C 4.1: AD-mix-β; methanesulfonamide; water / <i>tert</i>-butyl alcohol / 20 °C
  • 17
  • [ 479622-36-1 ]
  • [ 1163127-93-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: potassium hydroxide / ethanol / 1 h / Heating / reflux 1.2: 3 h / Heating / reflux 2.1: ammonium molibdate; dihydrogen peroxide / ethanol; water / 3 h / 65 °C 3.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 1.75 h / -78 - 20 °C 4.1: AD-mix-β; methanesulfonamide; water / <i>tert</i>-butyl alcohol / 20 °C 5.1: toluene-4-sulfonic acid / tetrahydrofuran / 36 h / 20 °C
  • 18
  • [ 479622-36-1 ]
  • C25H37N3O5Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: potassium hydroxide / ethanol / 1 h / Heating / reflux 1.2: 3 h / Heating / reflux 2.1: ammonium molibdate; dihydrogen peroxide / ethanol; water / 3 h / 65 °C 3.1: potassium hexamethylsilazane / 1,2-dimethoxyethane / 1.75 h / -78 - 20 °C 4.1: AD-mix-β; methanesulfonamide; water / <i>tert</i>-butyl alcohol / 20 °C 5.1: toluene-4-sulfonic acid / tetrahydrofuran / 36 h / 20 °C 6.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 °C
  • 19
  • [ 479622-36-1 ]
  • C17H26N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetrahydrofuran / 50 °C / Inert atmosphere 2: Siliacat DPP-Pd / tetrahydrofuran / 80 °C
  • 20
  • [ 479622-36-1 ]
  • C12H18N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: tetrahydrofuran / 50 °C / Inert atmosphere 2: Siliacat DPP-Pd / tetrahydrofuran / 80 °C 3: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
  • 21
  • [ 479622-36-1 ]
  • C10H18NO2Zn(1+)*I(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran at 50℃; Inert atmosphere; PREPARATION OF NTERMEDIATE 35 A solution of 3-iodomethylpyrrolidine-1-carboxylic acid tert-butyl ester (CAS:479622-36-1; 0.93 g, 3 mmol) in THF (6 mL) was pumped through a columncontaining activated Zn (12 g, 183.5 mmol) at 40 °C with flow of 0.5 mL/min. Theoutcome solution was collected under N2 atmosphere to yield intermediate 35 as a clearsolution that was used without any further manipulation.For the above reaction Zn was activated as follows: A solution of TMSC1 (0.75 mL)and 1-bromo-2-choroethane (0.3 mL) in THF (10 mL) was passed through the column containing Zn at 40 °C with a flow of 1 mL/min.
  • 22
  • [ 7440-66-6 ]
  • [ 479622-36-1 ]
  • ((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methyl)zinc(II) iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: zinc With chloro-trimethyl-silane; 1-Bromo-2-chloroethane In tetrahydrofuran at 40℃; Stage #2: 3-iodomethylpyrrolidine-1-carboxylic acid tert-butyl ester With lithium chloride In tetrahydrofuran at 40℃; PREPARATION OF INTERMEDIATE 37 A solution of 3-iodomethylpyrrolidine-l-carboxylic acid tert-butyl ester (CAS: 479622-36-1; 0.93 g, 3 mmol) in THF (6 mL) was pumped through a column containing activated Zn (12 g, 183.5 mmol) at 40 °C with a flow of 0.5 mL/min. The outcome solution was collected under N2 atmosphere to yield intermediate 37 as a clear solution that was used without any further manipulation. For the above reaction Zn was activated as follows: A solution of TMSC1 (0.75 mL) and l-bromo-2-choroethane (0.3 mL) in THF (10 mL) was passed through the column containing Zn at 40 °C with a flow of 1 mL/min.
  • 23
  • [ 479622-36-1 ]
  • C18H25N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 1 h / 20 °C
  • 24
  • [ 479622-36-1 ]
  • C13H17N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 1 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C
  • 25
  • [ 479622-36-1 ]
  • C18H25N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 18 h / 20 °C
  • 26
  • [ 479622-36-1 ]
  • C13H17N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 18 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C
  • 27
  • [ 479622-36-1 ]
  • C19H24F3N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 1 h / 20 °C
  • 28
  • [ 479622-36-1 ]
  • C18H21N5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tetrahydrofuran / 1 h / 50 °C 3.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C 3.2: 20 °C
  • 29
  • [ 479622-36-1 ]
  • C19H23N5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 1 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C 3.2: 20 °C
  • 30
  • [ 479622-36-1 ]
  • C19H23N5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 1 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C 4.1: sodium tris(acetoxy)borohydride; methanol / dichloromethane / 16 h / 20 °C
  • 31
  • [ 479622-36-1 ]
  • C19H23N5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 18 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C 4.1: sodium tris(acetoxy)borohydride; methanol / dichloromethane / 16 h / 20 °C
  • 32
  • [ 479622-36-1 ]
  • C20H22F3N5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 1 h / 20 °C 3.1: trifluoroacetic acid / dichloromethane / 0.5 h / 20 °C 3.2: 20 °C
  • 33
  • [ 479622-36-1 ]
  • C23H37N3O3Si [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / tetrahydrofuran / 1 h / 50 °C
  • 34
  • [ 479622-36-1 ]
  • C18H25N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: chloro-trimethyl-silane; 1-Bromo-2-chloroethane / tetrahydrofuran / 40 °C 1.2: 40 °C 2.1: palladium diacetate; ruphos / tetrahydrofuran / 1 h / 20 °C
  • 35
  • [ 288-32-4 ]
  • [ 479622-36-1 ]
  • C13H21N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% Stage #1: 1H-imidazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.166667h; Stage #2: 3-iodomethylpyrrolidine-1-carboxylic acid tert-butyl ester In N,N-dimethyl-formamide; mineral oil at 0 - 40℃; for 3h; 14 Synthesis of 2060-A. A solution of l/ -imidazole (115 mg, 1.69 mmol) in DMF (5 mL) was cooled to 0 °C and treated with NaH (60% in mineral oil, 122 mg, 3.1 mmol). The reaction mixture was stirred at 0 °C for 10 min, then tert- butyl 3-(iodomethyl)pyrrolidine-l- carboxylate (687 mg, 2.21 mmol) was added and the reaction mixture was warmed to 40 °C and stirred at 40 °C for 3 h. The mixture was thendiluted with water (30 mL) and extracted with EtOAc (20 mL x 3). The combined organic layers were washed with brine (20 mL x 3), dried over anhydrous Na2S04 and then concentrated in vacuo. The residue was purified by Prep-TLC (DCM : MeOH = 30 : 1) to give 2060-A (105 mg, 25%) as a colorless oil. MS 197.2 [M + H]+.
  • 36
  • [ 479622-36-1 ]
  • C15H22N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 16 h / 20 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 72 h / 60 °C / Inert atmosphere
  • 37
  • [ 479622-36-1 ]
  • C10H14N2*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 16 h / 20 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 72 h / 60 °C / Inert atmosphere 3: dichloromethane / 1 h / 0 - 20 °C
  • 38
  • [ 479622-36-1 ]
  • C22H19F2N5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 16 h / 20 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 72 h / 60 °C / Inert atmosphere 3: dichloromethane / 1 h / 0 - 20 °C 4: sodium carbonate / dimethyl sulfoxide / 2 h / 20 °C
  • 39
  • [ 479622-36-1 ]
  • C22H21F2N5O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 16 h / 20 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 72 h / 60 °C / Inert atmosphere 3: dichloromethane / 1 h / 0 - 20 °C 4: sodium carbonate / dimethyl sulfoxide / 2 h / 20 °C 5: hydrogen; palladium on activated charcoal / methanol; ethyl acetate / 0.83 h / 20 °C
  • 40
  • [ 479622-36-1 ]
  • C8H13N3*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C 1.2: 3 h / 0 - 40 °C 2.1: dichloromethane / 1 h / 0 - 20 °C
  • 41
  • [ 479622-36-1 ]
  • C20H18F2N6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C 1.2: 3 h / 0 - 40 °C 2.1: dichloromethane / 1 h / 0 - 20 °C 3.1: sodium carbonate / dimethyl sulfoxide / 2 h / 20 °C
  • 42
  • [ 479622-36-1 ]
  • C20H20F2N6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 0 °C 1.2: 3 h / 0 - 40 °C 2.1: dichloromethane / 1 h / 0 - 20 °C 3.1: sodium carbonate / dimethyl sulfoxide / 2 h / 20 °C 4.1: hydrogen; palladium on activated charcoal / methanol; ethyl acetate / 2 h / 20 °C
  • 43
  • [ 479622-36-1 ]
  • ((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methyl)zinc(II) iodide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With chloro-trimethyl-silane; ethylene dibromide; zinc In N,N-dimethyl acetamide at 20℃; for 16h; Inert atmosphere; 9 Synthesis of 2058-A. A mixture of zinc dust (896 mg, 13.8 mmol) and anhydrous DMA (3 mL) was treated with TMSC1 and l,2-dibromoethane (0.24 mL, v/v= 7/5), and the resulting reaction mixture was stirred at room temperature for 20 min under a N2 atmosphere. A solution of tert-butyl 3-(iodomethyl)pyrrolidine-l-carboxylate (3.3 g, 10.6 mmol) in anhydrous DMA (4 mL) was then added, and the resulting reaction mixture was stirred at room temperature for 16 h under a N2 atmosphere. The mixture was then used directly in the next step as 2058-A. The concentration of 2058-A was about 1.0 mol/L in DMA.
  • 44
  • [ 479622-36-1 ]
  • C14H21N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 16 h / 20 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 48 h / 60 °C / Inert atmosphere
  • 45
  • [ 479622-36-1 ]
  • C9H13N3*C2HF3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 16 h / 20 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 48 h / 60 °C / Inert atmosphere 3: dichloromethane / 1 h / 20 °C
  • 46
  • [ 479622-36-1 ]
  • C21H18F2N6O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 16 h / 20 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 48 h / 60 °C / Inert atmosphere 3: dichloromethane / 1 h / 20 °C 4: sodium carbonate / dimethyl sulfoxide / 2 h / 20 °C
  • 47
  • [ 479622-36-1 ]
  • C21H20F2N6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 16 h / 20 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 48 h / 60 °C / Inert atmosphere 3: dichloromethane / 1 h / 20 °C 4: sodium carbonate / dimethyl sulfoxide / 2 h / 20 °C 5: hydrogen; palladium on activated charcoal / methanol; ethyl acetate / 1 h / 20 °C
  • 48
  • [ 479622-36-1 ]
  • C21H20F2N6O [ No CAS ]
  • C21H20F2N6O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: zinc; chloro-trimethyl-silane; ethylene dibromide / N,N-dimethyl acetamide / 16 h / 20 °C / Inert atmosphere 2: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl acetamide / 48 h / 60 °C / Inert atmosphere 3: dichloromethane / 1 h / 20 °C 4: sodium carbonate / dimethyl sulfoxide / 2 h / 20 °C 5: hydrogen; palladium on activated charcoal / methanol; ethyl acetate / 1 h / 20 °C 6: Chiralpak AD-3 / methanol / Resolution of racemate
  • 49
  • 5,6-dimethoxy-2-(piperidin-4-ylmethyl)isoindolin-1-one hydrochloride [ No CAS ]
  • [ 479622-36-1 ]
  • tert-butyl 3-[(4-{(5,6-dimethoxy-1-oxoisoindolin-2-yl)methyl}piperidin-1-yl)methyl]pyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide for 16h;
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