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[ CAS No. 1170782-90-7 ] {[proInfo.proName]}

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Chemical Structure| 1170782-90-7
Chemical Structure| 1170782-90-7
Structure of 1170782-90-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1170782-90-7 ]

CAS No. :1170782-90-7 MDL No. :MFCD10758090
Formula : C6H12ClNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BQNOIBDCWPBGAS-UHFFFAOYSA-N
M.W : 165.62 Pubchem ID :21464884
Synonyms :

Calculated chemistry of [ 1170782-90-7 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 39.54
TPSA : 52.32 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) : -7.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.26
Log Po/w (WLOGP) : 0.64
Log Po/w (MLOGP) : 0.35
Log Po/w (SILICOS-IT) : 0.51
Consensus Log Po/w : 0.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.83
Solubility : 24.3 mg/ml ; 0.147 mol/l
Class : Very soluble
Log S (Ali) : -0.92
Solubility : 19.9 mg/ml ; 0.12 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.78
Solubility : 27.3 mg/ml ; 0.165 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.2

Safety of [ 1170782-90-7 ]

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

Application In Synthesis of [ 1170782-90-7 ]

* 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 [ 1170782-90-7 ]

[ 1170782-90-7 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1170782-90-7 ]
  • [ 459-57-4 ]
  • [ 1198470-63-1 ]
YieldReaction ConditionsOperation in experiment
With sodium acetate; sodium cyanoborohydride In methanol at 25℃; for 19h; 11.a a) 1-[(4-Fluoro-benzylamino)-methyl]-cyclopropanecarboxylic acid Methyl Ester (Trimethylsilyl)diazomethane (4.41 mL of a 1.0 M solution in diethyl ether, 8.82 mmol) was added over 5 min to a solution of racemic 1-(tert-butoxycarbonylamino-methyl)-cyclopropanecarboxylic acid (0.95 g, 4.41 mmol) in a 1:1 mixture of methanol/benzene (30 mL) at 0° C. The resulting yellow solution was stirred at 0° C. for 1 h, and then was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (20 mL) at 25° C. and a 4.0 M solution of hydrochloric acid in 1,4-dioxane (20 mL) was subsequently added. After stirring at 25° C. for 5 h, the reaction mixture was concentrated in vacuo to afford a sticky oil. This material was dissolved in toluene (80 mL) and the solution was concentrated in vacuo (the process was then repeated). The resulting residue was dissolved in methanol (30 mL) at 25° C. and 4-fluorobenzaldehyde (0.473 mL, 4.41 mmol), sodium acetate (0.723 g, 8.81 mmol), powdered/activated 4 Å molecular sieves (1.87 g) and sodium cyanoborohydride (0.554 g, 8.82 mmol) were added sequentially. The mixture was stirred at 25° C. for 19 h, then was filtered through Celite. The Celite was washed with methanol (2*30 mL) and the combined filtrate and washings were concentrated in vacuo. The residue was partitioned between half-saturated aqueous sodium bicarbonate solution (150 mL) and ethyl acetate (2*150 mL). The combined organic layers were dried over sodium sulfate and were concentrated in vacuo. The residue was purified by flash column chromatography (Teledyne Isco RediSep column; 50-100% ethyl acetate in hexanes) to afford 1-[(4-fluoro-benzylamino)-methyl]-cyclopropanecarboxylic acid methyl ester (0.050 g, 0.211 mmol, 5%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ: 0.79-0.82 (2H, m), 1.26-1.28 (2H, m), 2.70 (2H, s), 3.66 (3H, s), 3.79 (2H, s), 6.97-7.01 (2H, m), 7.28-7.31 (2H, m).
  • 2
  • [ 220145-17-5 ]
  • [ 1170782-90-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride In 1,4-dioxane at 25℃; for 5h; 11.a (Trimethylsilyl)diazomethane (4.41 mL of a 1.0 M solution in diethyl ether, 8.82 mmol) was added over 5 min to a solution of racemic 1-(tert-butoxycarbonylamino-methyl)-cyclopropanecarboxylic acid (0.95 g, 4.41 mmol) in a 1:1 mixture of methanol/benzene (30 mL) at 0° C. The resulting yellow solution was stirred at 0° C. for 1 h, and then was concentrated in vacuo. The residue was dissolved in 1,4-dioxane (20 mL) at 25° C. and a 4.0 M solution of hydrochloric acid in 1,4-dioxane (20 mL) was subsequently added. After stirring at 25° C. for 5 h, the reaction mixture was concentrated in vacuo to afford a sticky oil. This material was dissolved in toluene (80 mL) and the solution was concentrated in vacuo (the process was then repeated). The resulting residue was dissolved in methanol (30 mL) at 25° C. and 4-fluorobenzaldehyde (0.473 mL, 4.41 mmol), sodium acetate (0.723 g, 8.81 mmol), powdered/activated 4 molecular sieves (1.87 g) and sodium cyanoborohydride (0.554 g, 8.82 mmol) were added sequentially. The mixture was stirred at 25° C. for 19 h, then was filtered through Celite. The Celite was washed with methanol (2×30 mL) and the combined filtrate and washings were concentrated in vacuo. The residue was partitioned between half-saturated aqueous sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL). The combined organic layers were dried over sodium sulfate and were concentrated in vacuo. The residue was purified by flash column chromatography (Teledyne Isco RediSep column; 50-100% ethyl acetate in hexanes) to afford 1-[(4-fluoro-benzylamino)-methyl]-cyclopropanecarboxylic acid methyl ester (0.050 g, 0.211 mmol, 5%) as a pale yellow oil. 1H NMR (400 MHz, CDCl3) δ: 0.79-0.82 (2H, m), 1.26-1.28 (2H, m), 2.70 (2H, s), 3.66 (3H, s), 3.79 (2H, s), 6.97-7.01 (2H, m), 7.28-7.31 (2H, m).
  • 3
  • [ 1170782-90-7 ]
  • [ 1428988-52-6 ]
  • 1-[([17-(5-fluoropyridin-3-yl)estra-1,3,5(10),16-tetraen-3-yl]carbonyl}amino)-methyl]cyclopropan-1-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
3 1-[([17-(5-Fluoropyridin-3-yl)estra-1,3,5(10),16-tetraen-3-yl]carbonyl}amino)methyl]-cyclopropane-1-carboxylic acid EXAMPLE 3 1-[([17-(5-Fluoropyridin-3-yl)estra-1,3,5(10),16-tetraen-3-yl]carbonyl}amino)methyl]-cyclopropane-1-carboxylic acid Analogously to Example 1, 100 mg (0.26 mmol) of 17-(5-fluoropyridin-3-yl)estra-1,3,5(10),16-tetraene-3-carboxylic acid and 88 mg (2.0 equiv.) of methyl 1-(aminomethyl)cyclopropane-1-carboxylate hydrochloride were converted into 72 mg (57% of theory) of the title compound. C29H31FN2O3 (474.6). MS-ES+ mass found: 474.23. 1H-NMR (300 MHz, DMSO-d6): δ [ppm]=0.82-0.90 (m, 2H), 0.95-1.06 (m, 5H), 1.33-1.81 (m, 5H), 1.56 (d, 3H), 1.84-1.97 (m, 1H), 1.84-1.97 (m, 1H), 2.05-2.44 (m), 2.80-2.94 (m, 2H), 3.44-3.54 (m, 2H), 6.27 (s., 1H), 7.31 (d, 1H), 7.50-7.60 (m, 2H), 7.68 (dt, 1H), 8.18 (t, 1H), 8.43 (d, 1H), 8.49 (s, 1H), 12.3 (s, 1H).
  • 4
  • [ 865298-83-5 ]
  • [ 1170782-90-7 ]
  • C27H33FN4O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With methanesulfonato(2-di-t-butylphosphino-2’,4’,6’-tri-i-propyl-1,1'-biphenyl)(2’-amino-1,1'-biphenyl-2-yl)palladium(II); 1-ethyl-2,2,4,4,4-pentakis(dimethylamino)-2λ5,4λ5-catenadi(phosphazene) In dimethyl sulfoxide at 20℃; for 2h;
  • 5
  • [ 1170782-90-7 ]
  • 1-[(2-fluorobenzenesulfonylamino)methyl]cyclopropylcarboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.08 h / 20 °C 1.2: 3 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 20 °C
Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.08 h / 20 °C 1.2: 3 h / 20 °C 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 16 h / 20 °C
  • 6
  • [ 1170782-90-7 ]
  • 1-[(2-fluorobenzenesulfonylamino)methyl]-N-(5-hydroxyadamantan-2-yl)cyclopropanecarboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.08 h / 20 °C 1.2: 3 h / 20 °C 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 20 °C 3.1: triethylamine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride / dichloromethane / 4 h / 20 °C
Multi-step reaction with 3 steps 1.1: triethylamine / dichloromethane / 0.08 h / 20 °C 1.2: 3 h / 20 °C 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 16 h / 20 °C 3.1: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / dichloromethane / 4 h / 20 °C
  • 7
  • [ 1170782-90-7 ]
  • [ 2905-21-7 ]
  • 1-[(2-fluorobenzenesulfonylamino)methyl]-1-cyclopropylcarboxylic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 1-(aminomethyl)cyclopropylcarboxylic acid methylester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: 2-fluorobenzenesulfonyl chloride In dichloromethane at 20℃; for 3h; P.3 Preparation of 1-[(2-fluoro-benzenesulfonylamino)methyl]-1-cyclopropylcarboxylic acid methyl ester Preparational Example 3 Preparation of 1-[(2-fluoro-benzenesulfonylamino)methyl]-1-cyclopropylcarboxylic acid methyl ester 150 (0.91 mmol) mg of the 1-(aminomethyl)-cyclopropylcarboxylic acid methylester hydrochloride prepared in Preparational Example 2 was dissolved in 3 ml of methylene chloride, to which 0.25 ml of TEA was added, followed by stirring at room temperature for 5 minutes. 194 mg (1.0 mmol) of 2-fluorosulfonylchloride was added to the reactant, followed by stirring at room temperature for 3 hours, followed by evaporation under reduced pressure to eliminate the reaction solvent. The residue was dissolved in 5 ml of water, followed by extraction with 310 ml of ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and evaporated under reduced pressure, followed by column chromatography to give 215 mg of 1-[(2-fluoro-benzenesulfonylamino)methyl]-cyclopropylcarboxylic acid methyl ester (yield: 83%). 1H NMR (400 MHz, CDCl3) δ 7.86-7.92 (m, 1H), 7.56-7.60 (m, 1H), 7.20-7.32 (m, 2H), 5.67 (d, J=5.2 Hz, 1H), 3.64-3.72 (m, 3H), 3.14-3.21 (m, 2H), 1.17-1.21 (m, 2H), 0.84-0.91 (m, 2H)
83% Stage #1: 1-(aminomethyl)cyclopropylcarboxylic acid methylester hydrochloride With triethylamine In dichloromethane at 20℃; for 0.0833333h; Stage #2: 2-fluorobenzenesulfonyl chloride In dichloromethane at 20℃; for 3h; 3 Preparation of 1-[(2-fluorobenzenesulfonylamino)methyl]-cyclopropylcarboxylic acid methyl ester 150 (0.91 mmol) mg of the 1-(aminomethyl)-cyclopropylcarboxylic acid methylester hydrochloride prepared in Preparational Example 2 was dissolved in 3 ml of methylene chloride, to which 0.25 ml of TEA was added, followed by stirring at room temperature for 5 minutes. 194 mg (1.0 mmol) of 2-fluorosulfonylchloride was added to the reactant, followed by stirring at room temperature for 3 hours, followed by evaporationunder reduced pressure to eliminate the reaction solvent. The residue was dissolved in 5 ml of water, followed by extraction with 310 ml of ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and evaporated under reduced pressure, followed by column chromatography to give 215 mg of 1-[(2-fluorobenzenesulfonylamino)methyl]-cyclopropylcarboxylic acid methyl ester (yield: 83%). 1H NMR (400 MHz, CDCl3) δ 7.86-7.92 (m, 1H), 7.56-7.60 (m, 1H), 7.20-7.32 (m, 2H), 5.67 (d, J = 5.2 Hz, 1H), 3.64-3.72 (m, 3H), 3.14-3.21 (m, 2H), 1.17-1.21 (m, 2H), 0.84-0.91 (m, 2H)
  • 8
  • [ 67-56-1 ]
  • [ 1421601-23-1 ]
  • [ 1170782-90-7 ]
YieldReaction ConditionsOperation in experiment
98% With thionyl chloride; In methanol; at 20℃; for 3h; Preparational Example 2 Preparation of 1-(aminomethyl)-cyclopropylcarboxylic acid methylester hydrochloride 273 mg (1.8 mmol) of the 1-(aminomethyl)-cyclopropylacetic acid hydrochloride prepared in Preparational Example 1 was dissolved in 6 ml of methanol, to which 0.26 ml (3.6 mmol) of thionyl chloride was added, followed by stirring at room temperature for 3 hours. Upon completion of the reaction, the solvent was evaporated under reduced pressure to give 291 mg of 1-(aminomethyl)-cyclopropylcarboxylic acid methylester hydrochloride (yield: 98%). 1H NMR (400 MHz, D2O) δ 3.60 (s, 3H), 3.06 (s, 2H), 1.28-1.31 (m, 2H), 0.97-0.99 (m, 2H)
98% With thionyl chloride; at 20℃; for 3h; 273 mg (1.8 mmol) of the 1-(aminomethyl)-cyclopropylacetic acid hydrochloride prepared in Preparational Example 1 was dissolved in 6 ml of methanol, to which 0.26 ml (3.6 mmol) of thionyl chloride was added, followed by stirring at room temperature for 3 hours. Upon completion of the reaction, the solvent was evaporated under reduced pressure to give 291 mg of 1-(aminomethyl)-cyclopropylcarboxylic acid methylester hydrochloride (yield: 98%). 1H NMR (400 MHz, D2O δ 3.60 (s, 3H), 3.06 (s, 2H), 1.28-1.31 (m, 2H), 0.97-0.99 (m, 2H)
  • 9
  • [ 1170782-90-7 ]
  • 1-(4-phenoxyphenyl)-2-thiocyanatoethanone [ No CAS ]
  • C21H20N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With sodium hydrogencarbonate In ethanol at 50℃; for 16h; 1.3.3 Synthesis of 3.3 [00305] To a solution of compound 3.2 (2.5 g, 9.2 mmol) and amine (1.54 g, 9.2 mmol) in EtOH (120 mL) was added NaHC03 (1.56 g, 18.6 mmol). The mixture was stirred at 50 °C for 16 h. The solvent was removed andthe residue purified by silica gel chromatography (PE/EA=l0/l) to give the desired compound 3.3 (1.7 g, Y: 48%) as a yellow solid. ESI-MS (M+H) +: 381.1. 1H NMR: (400 MHz, DMSO-e) d: 7.84 (d, J=8.8, 2H), 7.34 (t, =8, 2H), 7.13-7.10 (m, 5H), 3.70 (s, 3H), 3.51 (d, =6.4, 2H), 5.07 (s, 2H), 1.33-1.30 (m, 2H), 1.27-1.24 (m, 2H).
  • 10
  • [ 1170782-90-7 ]
  • [ 1355361-72-6 ]
  • methyl 1-([8-(cyclohexyloxy)-1-oxo-2-phenyl-1H-pyrido[2,1-b][1,3]benzothiazol-4-yl]carbonyl}amino)cyclopropanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 20℃; for 3h; Inert atmosphere; Green chemistry; 5.1.2 General procedure procedure for the amidation reaction for compounds 25, 26 and 40-44 (method B) General procedure: Under N2 atmosphere, to a mixture of the appropriate acid (1.0 mmol), and the appropriate amino acid methyl ester hydrochloride or the desired amine (1.3 mmol) in dry DMSO (15 mL), TBTU coupling reagent (1.3 mmol), and DIPEA (4.6 mmol) were added. After stirring at room temperature, the reaction mixture was poured into ice/water and acidified with 2 N HCl (pH = 4-5) to give a precipitate which was filtered under vacuum to give the relative solid which was purified, as described below for each compound, in order to obtain the desired PBTZ derivative.
  • 11
  • [ 1170782-90-7 ]
  • 7-benzyloxy-4-(3,4-difluorophenyl)-3-isopropenyl-1-oxidoquinolin-1-ium [ No CAS ]
  • methyl 1-[[[7-benzyloxy-4-(3,4-difluorophenyl)-3-isopropenyl-2-quinolyl]amino]methyl]cyclopropanecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 50℃; for 48h; 1.A.3 Step 3: methyl 1-[[[7-benzyloxy-4-(3,4-difluorophenyl)-3-isopropenyl-2- quinolyl]amino]methyl]cyclopropanecarboxylate (Cl 73) To a solution of C172 (335 mg, 0.8304 mmol), methyl 1- (aminomethyl)cyclopropanecarboxylate hydrochloride (412.6 mg, 2.49 mmol) in dichloromethane (10 mL), DIEA (536.6 mg, 0.75 mL, 4.152 mmol) and PyBrop (1.1614 g, 2.4912 mmol) were added. The reaction was heated at 50 °C for 2 days. The mixture was diluted with dichloromethane (20 mL), washed successively with an aqueous solution of NaHCCh (10 mL) and water (10 mL), dried over NaiSCL and concentrated. Purification by silica gel chromatography (30-50% EtOAc in hexane) to afford C173 (70 mg, 9%). LCMS m/z 515.0 [M+H]+
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