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[ CAS No. 57248-14-3 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 57248-14-3
Chemical Structure| 57248-14-3
Chemical Structure| 57248-14-3
Structure of 57248-14-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 57248-14-3 ]

CAS No. :57248-14-3 MDL No. :MFCD00041441
Formula : C5HCl3OS Boiling Point : -
Linear Structure Formula :- InChI Key :YGDFSMANOSKQRU-UHFFFAOYSA-N
M.W :215.48 Pubchem ID :2777084
Synonyms :

Calculated chemistry of [ 57248-14-3 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.52
TPSA : 45.31 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.75 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.08
Log Po/w (XLOGP3) : 4.03
Log Po/w (WLOGP) : 3.43
Log Po/w (MLOGP) : 2.24
Log Po/w (SILICOS-IT) : 4.37
Consensus Log Po/w : 3.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.02
Solubility : 0.0206 mg/ml ; 0.0000957 mol/l
Class : Moderately soluble
Log S (Ali) : -4.68
Solubility : 0.00445 mg/ml ; 0.0000207 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -3.47
Solubility : 0.073 mg/ml ; 0.000339 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.5

Safety of [ 57248-14-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P260-P280-P310 UN#:3265
Hazard Statements:H335-H314-H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 57248-14-3 ]

* 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 [ 57248-14-3 ]

[ 57248-14-3 ] Synthesis Path-Downstream   1~34

  • 1
  • [ 57248-14-3 ]
  • [ 120618-67-9 ]
  • [ 133042-27-0 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane at 0℃; for 0.5h;
  • 2
  • [ 57248-14-3 ]
  • [ 120-20-7 ]
  • [ 98215-53-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In chloroform for 2h; Ambient temperature; Yield given;
YieldReaction ConditionsOperation in experiment
2.5-Dichlor-thiophen-3-carbonsaeure, SOCl2 (exotherm. Rk., dann Siedetemp., 4 Std.); nicht rein isoliert;
  • 4
  • [ 57248-14-3 ]
  • [ 6638-79-5 ]
  • [ 210097-99-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In chloroform at 0 - 20℃;
  • 5
  • [ 36157-41-2 ]
  • [ 57248-14-3 ]
YieldReaction ConditionsOperation in experiment
100% With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 2.5h; To a suspension of <strong>[36157-41-2]2,5-dichloro-thiophene-3-carboxylic acid</strong> (49.7 g; 252.23 mmoles; 1.00 equiv) in dichloromethane (500 mL), add dimethylformamide (0.5 mL; 6.47 mmoles) followed by a solution of 2 M oxalyl chloride in dichloromethane (138.73 mL; 277.45 mmoles; 1.1 equiv) over 1.5 hr. (vent the evolved gas through a caustic solution). Stir the resulting clear solution at room temperature for 1 hr. until gas evolution has ceased and the reaction is complete by LCMS (quench a sample into 7 M NH3/MeOH for reaction monitoring) MS (m/z): = 195.9, 197.9 (M+H)+ forcorresponding primary amide. Evaporate to dryness to give the title intermediate as a brown oil (55 g, 252 mmol, quantitative).
100% With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 2.5h; To a suspension of<strong>[36157-41-2]2,5-dichloro-thiophene-3-carboxylic acid</strong> (49.7 g; 252.23mmoles; 1.00 equiv) in dichloromethane (500 mL), add dimethylformamide (0.5 mL;15 6.47 mmoles) followed by a solution of 2M oxalyl chloride in dichloromethane (138.73mL; 277.45 mmoles; 1.1 equiv) over 1.5 hr. (vent the evolved gas through a causticsolution). Stir the resulting clear solution at room temperature for 1 hr. until gasevolution has ceased and the reaction is complete by LCMS (quench a sample into 7 MNH3/MeOH for reaction monitoring) MS (m/z): = 195.9, 197.9 (M+Ht for20 corresponding primary amide. Evaporate to dryness to give the title intermediate as abrown oil (55 g, 252 mmol, quantitative).
  • 6
  • [ 1018975-59-1 ]
  • [ 57248-14-3 ]
  • 1-[5-(2,5-dichloro-3-thienyl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With N-ethyl-N,N-diisopropylamine In acetonitrile at 150℃; for 0.5h; Microwave irradiation; 284 Example 2841-[5-(2,5-Dichloro-3-thienyl)-1,2,4-oxadiazol-3-yl]methyl}-2-propyl-4- (trifluoromethyl)-1H-indole-5-carbonitrile; To a solution of 2-[5-cyano-2-propyl-4-(trifluoromethyl)-1 /-/-indol-1-yl]-Λ/- hydroxyethanimidamide (Example 275A) (0.100 g, 0.308 mmol) in anhydrous acetonitrile (3.0 ml_) under N2, was added 2,5-dichloro-3-thiophenecarbonyl chloride (0.265 g, 1.23 mmol) and N,N-diisopropylethylamine (0.50 ml_, 5.21 mmol). The mixture was then heated in a microwave at 15O0C for 30 min. Upon cooling, the mixture was poured onto a biotage prepak column and the mixture was purified by flash chromatography (0-25% EtOAc-hexanes gradient) to give 0.055g (37% yield) of pure product: MS (ES) m/z 485 (M+1 ).
  • 7
  • [ 57248-14-3 ]
  • 4-(2,5-dichloro-thiophen-3-ylmethyl)-1<i>H</i>-imidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: Et3N / CHCl3 / 0 - 20 °C 2: CH2Cl2 / 20 °C 3: NaBH4 / propan-2-ol / 2 h / Heating 4: NaBH4; TFA / 0 - 20 °C
  • 8
  • [ 57248-14-3 ]
  • [ 334918-23-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: Et3N / CHCl3 / 0 - 20 °C 2: CH2Cl2 / 20 °C 3: NaBH4 / propan-2-ol / 2 h / Heating
  • 9
  • [ 57248-14-3 ]
  • [ 334918-28-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: Et3N / CHCl3 / 0 - 20 °C 2: CH2Cl2 / 20 °C
  • 10
  • [ 57248-14-3 ]
  • [ 98215-64-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / CHCl3 / 2 h / Ambient temperature 2: POCl3 / toluene / 3.5 h / Heating
  • 11
  • [ 179556-97-9 ]
  • [ 57248-14-3 ]
  • N-(2-methylpropyl)-N-[(2,5-dichlorothiophen-3-yl)-carbonyl]piperidin-1-carboxylic acid ter-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 3h; 22 To a cooled (0°C) solution of 4-isobutylamino-piperidine-1-carboxylic acid tert-butyl ester (1.6g, 6. 1mmol) in dry dichloromethane is added diisopropylethylamine (l. lml, 6. 1mmol) and 2,5-dichloro-thiophenecarbonyl chloride (l. lg, 5. 1mmol). The reaction mixture is stirred for 3 hours at 0°C, then quenched with saturated aqueous NaHCO3. The layers are separated and the aqueous layer is extracted with ethyl acetate. The combined organic extracts are washed with an aqueous saturated brine solution, dried over anhydrous Na2S04, filtered, and concentrated in vacuo. The crude mixture is purified on silica gel 0-15% ethyl acetate/hexanes to give N-(2-methylpropyl)-N-[(2, 5- dichlorothiophen-3-yl) -carbonyl] piperidin-l-carboxylic acid ter-butyl ester (1.73g, 79%). The 1H NMR spectrum acquired in CDC13 showed evidence of rotomers. 1H NMR (CDC13) : 5 = 6. 75 (2H, s), 4.29-4. 10 (5H, m), 3.63-3. 57 (1H, m), 3.17 (2H, d), 3.08 (2H, d), 2.82-2. 76 (2H, m), 2.59 (2H, brs), 2.16-2. 13 (1H, m), 1.90-1. 79 (3H, m), 1.69-1. 62 (3H, m), 1.47-1. 46 (18H, d), 1.32-1. 25 (3H, m), 0.96 (6H, d), 0.79 (6H, d).
  • 12
  • [ 57248-14-3 ]
  • [ 219765-84-1 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: 2,5-dichlorothiophene-3-carbonyl chloride With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: With hydrogenchloride; water In tetrahydrofuran Acidic conditions;
  • 13
  • N'-(tert-butyl)-4-methylbenzohydrazide [ No CAS ]
  • [ 57248-14-3 ]
  • N'-t-butyl-N-(4-methyl-benzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)-hydrazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide In water; toluene Preparation of N'-t-butyl-N-(4-methyl-benzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)-hydrazine Preparation of N'-t-butyl-N-(4-methyl-benzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)-hydrazine N'-t-butyl-N-4-methylbenzoylhydrazine (0.7 g) was dissolved in 35 ml toluene. Water (5 ml) and 50% aqueous sodium hydroxide (0.8 g) were added followed by 2,5-dichlorothiophene-3-carbonylchloride (2.0 g). After stirring for 3 hours at room temperature, ether was added and the organic layer separated. Evaporation afforded a solid which was triturated with 10% ether-hexane to afford N'-t-butyl-N-(4-methylbenzoyl)-N'-(2,5-dichlorothiophene-3-carbonyl)hydrazine. m.p. 163-165° C.
  • 14
  • [ 57248-14-3 ]
  • [ 210098-12-7 ]
YieldReaction ConditionsOperation in experiment
51% With methylamine In dichloromethane 52 N-Methyl-(2,5-dichlorothiophen-3-yl)carboxamide N-Methyl-(2,5-dichlorothiophen-3-yl)carboxamide To a stirred solution of 2,5-dichloro-3-thenoyl chloride (commercially available from Maybridge Chemical Co. Ltd. 1.07 g, 5 mM) in CH2 Cl2 (5 mL) was added 40% aqueous solution of methylamine (1 mL) at room temperature. After stirring overnight, the mixture was poured into CH2 Cl2 (50 mL). The whole was washed with water (40 mL), brine (40 mL), dried over MgSO4, and concentrated in vacuo. The resulting solid was triturated with Et2 O-hexane to give the subtitle compound (0.54 g, 51% yield). 1 H--NMR (CDCl3) δ 7.22 (s, 2H), 3.00 (s, 3H), 2.98 (s, 3H).
  • 15
  • [ 57248-14-3 ]
  • [ 75-35-4 ]
  • [ 846576-52-1 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,5-dichlorothiophene-3-carbonyl chloride With aluminum (III) chloride In dichloromethane at 0℃; for 0.5h; Stage #2: 1,1-Dichloroethylene In dichloromethane at 0 - 20℃; 049] INTERMEDIATE 1 3, 3-DICHLORO-1- (2, 5-DICHLORO-3-THIEN L-2-ROPEN-1-ONE [050] To a suspension OF ALCL3 (0. 93 g, 6.96 mmol) in CH2C12 (10 mL) at 0°C, 2,5-dichloro-3- thiophenecarbonyl chloride (1.0 g, 4.64 mmol) was added. The reaction mixture was stirred for 30 minutes before vinylidene chloride (1.48 mL, 18.6 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature overnight. The mixture was poured into ice and extracted with CH2C12. The combined organic layer was washed with water, brine, and dried (NA2SO4). Removal of the solvents under reduced pressure afforded 1.28 g of crude 3,3-dichloro- 1-(2, 5-DICHLORO-3-THIENYL)-2-PROPEN-1-ONE, which was taken on without any further purification. RT (HPLC) : 3.14 min; MIT" : 275.
  • 16
  • [ 57248-14-3 ]
  • [ 333-20-0 ]
  • [ 1140909-68-7 ]
YieldReaction ConditionsOperation in experiment
In acetonitrile at 22℃;
  • 17
  • [ 57248-14-3 ]
  • [ 4302-52-7 ]
  • C15H10Cl2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
  • 18
  • [ 57248-14-3 ]
  • [ 772-38-3 ]
  • C17H14Cl2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
  • 19
  • [ 57248-14-3 ]
  • [ 536-74-3 ]
  • C13H6Cl2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
  • 20
  • [ 57248-14-3 ]
  • [ 693-02-7 ]
  • C11H10Cl2OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;
  • 21
  • [ 57248-14-3 ]
  • 3-[4-(2-chloro-8-methyl-thieno[2,3-b][1,5]benzoxazepin-4-yl)piperazin-1-yl]-2,2-dimethyl-propanoic acid dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2.1: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C 3.1: trichlorophosphate; <i>N</i>,<i>N</i>-dimethyl-aniline / 2.5 h / 60 - 100 °C 4.1: potassium carbonate / acetonitrile 4.2: 30 h / 80 °C 5.1: sodium hydroxide / isopropyl alcohol; water / 2.5 h / 80 °C 5.2: pH 7 6.1: hydrogenchloride / acetonitrile; 1,4-dioxane
  • 22
  • [ 57248-14-3 ]
  • [ 1418130-86-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C
Multi-step reaction with 2 steps 1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C
  • 23
  • [ 57248-14-3 ]
  • [ 1418130-87-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C 3: trichlorophosphate; <i>N</i>,<i>N</i>-dimethyl-aniline / 2.5 h / 60 - 100 °C
Multi-step reaction with 3 steps 1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C 3: <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate / 2.5 h / 60 - 100 °C
  • 24
  • [ 57248-14-3 ]
  • [ 1418130-88-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2.1: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C 3.1: trichlorophosphate; <i>N</i>,<i>N</i>-dimethyl-aniline / 2.5 h / 60 - 100 °C 4.1: potassium carbonate / acetonitrile 4.2: 30 h / 80 °C
Multi-step reaction with 4 steps 1.1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2.1: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C 3.1: <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate / 2.5 h / 60 - 100 °C 4.1: potassium carbonate / acetonitrile 4.2: 30 h / 80 °C
  • 25
  • [ 57248-14-3 ]
  • [ 1418130-83-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2.1: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C 3.1: trichlorophosphate; <i>N</i>,<i>N</i>-dimethyl-aniline / 2.5 h / 60 - 100 °C 4.1: potassium carbonate / acetonitrile 4.2: 30 h / 80 °C 5.1: sodium hydroxide / isopropyl alcohol; water / 2.5 h / 80 °C 5.2: pH 7
  • 26
  • [ 57248-14-3 ]
  • [ 2835-98-5 ]
  • [ 1418130-85-4 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine In tetrahydrofuran at 15 - 20℃; for 1.5h; 2 Preparation 2. 2,5-dichloro-N-(2-hydroxy-4-methyl-phenyl)thiophene-3- carboxamide To a solution of 6-amino-m-cresol (34.14 g; 277.20 mmoles; 1.1 equiv) in THF (450 mL), add pyridine (40.76 mL; 504.00 mmoles; 2 equiv), followed by a solution of 2,5-dichlorothiophene-3-carbonyl chloride (54.30 g, 252 mmoles, 1.00 equiv) in THF (250 mL) over 30 min., using an ice-bath to maintain a temperature of 15-20°C. Stir the resulting thick mixture at room temperature for 1 hr. to give complete consumption of the aminophenol by LC-MS. Pour onto a mixture of 2 M aqueous HC1 (500 ml) and ice (250 ml) with agitation. Collect the resulting beige solid by filtration, wash well with water, and dry in air. MS (m/z): = 301.84, 303.94 (M+H)+. Dry in a vacuum oven at 40°C over P2O5 overnight to give the title intermediate (84.5g, assumed quantitative).
84.5 g With pyridine In tetrahydrofuran at 15 - 20℃; for 1.5h; 2 Preparation 2. 2,5-dichloro-N-(2-hydroxy-4-methyl-phenyl)thiophene-3-carboxamide To a solution of 6-amino-m-cresol (34.14 g; 277.20 mmoles; 1.1 equiv) in THF(450 mL), add pyridine (40.76 mL; 504.00 mmoles; 2 equiv), followed by a solution of2,5-dichlorothiophene-3-carbonyl chloride (54.30 g, 252 mmoles, 1.00 equiv) in THF(250 mL) over 30 min., using an ice-bath to maintain a temperature of 15-20°C. Stir the5 resulting thick mixture at room temperature for 1 hr. to give complete consumption of theaminophenol by LCMS. Pour onto a mixture of 2M aqueous HCl (500 ml) and ice (250ml) with agitation. Collect the resulting beige solid by filtration, wash well with water,and dry in air. MS (m/z): = 301.84, 303.94 (M+Ht. Dry in a vacuum oven at 40°C overP20s overnight to give the title intermediate (84.5g, assume quantitative).
  • 27
  • [ 57248-14-3 ]
  • [ 1246249-16-0 ]
  • [ 1246249-59-1 ]
YieldReaction ConditionsOperation in experiment
79% With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; 27 Preparation of 2-(4-(4-(2,5-Dichlorothiophene-3-carbonyl)piperazin-1-yl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one To a mixture of 5,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-one (0.150 g, 0.41 mmol) and 2,5-dichlorothiophene-3-carbonyl chloride (0.088 g, 0.41 mmol) in CH2Cl2 was added Et3N (0.086 mL, 0.62 mmol) and the mixture stirred at room temperature under nitrogen for 30 minutes. The mixture was concentrated and purified by silica gel chromatography, eluting with 70% CH2Cl2/(92:7:1 CHCl3/MeOH/concentrated NH4OH) to 100% (92:7:1 CHCl3/MeOH/concentrated NH4OH), to afford the title compound as a light yellow solid (0.177 g, 79%). 1H NMR (300 MHz, DMSO-d6): δ 11.80 (s, 1H), 8.12 (d, J=9.0 Hz, 2H), 7.27 (s, 1H), 7.05 (d, J=9.0 Hz, 2H), 6.69 (d, J=2.3 Hz, 1H), 6.48 (d, J=2.3 Hz, 1H), 3.88 (s, 3H), 3.84 (s, 3H), 3.73-3.82 (m, 2H), 3.38-3.44 (m, 6H). APCI MS m/z 545 [M+H]+
79% With triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; 27 Preparation of 2-(4-(4-(2,5-Dichlorothiophene-3-carbonyl)piperazin-1-yl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one Example 27 Preparation of 2-(4-(4-(2,5-Dichlorothiophene-3-carbonyl)piperazin-1-yl)phenyl)-5,7-dimethoxyquinazolin-4(3H)-one To a mixture of 5,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinazolin-4(3H)-one (0.150 g, 0.41 mmol) and 2,5-dichlorothiophene-3-carbonyl chloride (0.088 g, 0.41 mmol) in CH2Cl2 was added Et3N (0.086 mL, 0.62 mmol) and the mixture stirred at room temperature under nitrogen for 30 minutes. The mixture was concentrated and purified by silica gel chromatography, eluting with 70% CH2Cl2/(92:7:1 CHCl3/MeOH/concentrated NH4OH) to 100% (92:7:1 CHCl3/MeOH/concentrated NH4OH), to afford the title compound as a light yellow solid (0.177 g, 79%). 1H NMR (300 MHz, DMSO-d6): δ 11.80 (s, 1H), 8.12 (d, J=9.0 Hz, 2H), 7.27 (s, 1H), 7.05 (d, J=9.0 Hz, 2H), 6.69 (d, J=2.3 Hz, 1H), 6.48 (d, J=2.3 Hz, 1H), 3.88 (s, 3H), 3.84 (s, 3H), 3.73-3.82 (m, 2H), 3.38-3.44 (m, 6H). APCI MS m/z 545 [M+H]+.
  • 28
  • [ 57248-14-3 ]
  • [ 1619926-26-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2.1: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C 3.1: <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate / 2.5 h / 60 - 100 °C 4.1: potassium carbonate / acetonitrile 4.2: 30 h / 80 °C 5.1: tripotassium phosphate "n" hydrate; tricyclohexylphosphine tetrafluoroborate; palladium diacetate / water; toluene / 100 °C / Inert atmosphere
  • 29
  • [ 57248-14-3 ]
  • [ 1619926-24-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2.1: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C 3.1: <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate / 2.5 h / 60 - 100 °C 4.1: potassium carbonate / acetonitrile 4.2: 30 h / 80 °C 5.1: tripotassium phosphate "n" hydrate; tricyclohexylphosphine tetrafluoroborate; palladium diacetate / water; toluene / 100 °C / Inert atmosphere 6.1: sodium hydroxide; water / isopropyl alcohol / 0.75 h / 85 °C
  • 30
  • [ 57248-14-3 ]
  • 3-[4-(2-cyclopropyl-8-methylthieno[2,3-b][1,5]benzoxazepin-4-yl)piperazin-1-yl]-2,2-dimethylpropanoic acid dihydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: pyridine / tetrahydrofuran / 1.5 h / 15 - 20 °C 2.1: potassium carbonate / dimethyl sulfoxide / 4.5 h / 100 - 110 °C 3.1: <i>N</i>,<i>N</i>-dimethyl-aniline; trichlorophosphate / 2.5 h / 60 - 100 °C 4.1: potassium carbonate / acetonitrile 4.2: 30 h / 80 °C 5.1: tripotassium phosphate "n" hydrate; tricyclohexylphosphine tetrafluoroborate; palladium diacetate / water; toluene / 100 °C / Inert atmosphere 6.1: sodium hydroxide; water / isopropyl alcohol / 0.75 h / 85 °C 7.1: hydrogenchloride / acetonitrile; water
  • 31
  • [ 57248-14-3 ]
  • [ 846576-54-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C 1.2: 0 - 20 °C 2.1: triethylamine / 1,4-dioxane / 2 h / 0 - 20 °C 3.1: sodium hydride / tetrahydrofuran / 90 h / 20 °C / Heating / reflux
  • 32
  • [ 57248-14-3 ]
  • N-(2-(4-aminophenyl)benzo[d]oxazol-5-yl)-4-methoxybenzenesulfonamide [ No CAS ]
  • 2,5-dichloro-N-(4-(5-((4-methoxyphenyl)sulfonamido)benzo[d]oxazol-2-yl)phenyl)thiophene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane General procedure for the amide and sulfonamide coupling step to give methoxy analogs 35-to-49-OMe. General procedure: To stirring mixtures of 53 (1eq.) in anhydrous CH2Cl2 were added the respective R2-COCl or R2-SO2Cl (1.2eq.) reagents and pyridine (1.2eq.). Note that for any analogs where the R2-CO2H starting materials were only commercially available, the acids were first converted to the acid chlorides by stirring in thionyl chloride at 60°C for 1h, then concentrating. The reactions were allowed to stir at room temperature for 18h, then were diluted with hexanes. The precipitates were filtered, rinsed with water, and collected. Flash chromatographic purification (either normal-phase with hexanes:EtOAc gradients, or reverse-phase with a water:MeOH gradients) afforded the products as solids. If necessary, products were further purified by preparatory RP-HPLC (water:CH3CN gradients), concentrated, and lyophilized. Refer to the Supporting Information for individual compound characterization data.
  • 33
  • [ 57248-14-3 ]
  • N-(2-(4-aminophenyl)benzo[d]oxazol-5-yl)-4-methoxybenzenesulfonamide [ No CAS ]
  • 2,5-dichloro-N-(4-(5-((4-hydroxyphenyl)sulfonamido)benzo[d]oxazol-2-yl)phenyl)thiophene-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane 2: boron tribromide / dichloromethane / 18 h / 20 °C / Inert atmosphere
  • 34
  • [ 57248-14-3 ]
  • [ 18856-68-3 ]
  • C12H13Cl2NO3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In benzene at 5 - 85℃; for 2h; A mixture of 2,5-dichlorothiophene-3-carboxylic acid 4 (5 g, 25.4 mmol), and thionyl chloride (SOCl2) (12.0g, 101 mmol) were dissolved in dry benzene (60 mL), then refluxed for 4-5 h under anhydrous conditions. The solvent and excess thionyl chloride were distilled under reduced pressure, dry benzene (20 mL) was then added to remove the trace of thionyl chloride, and re-distilled. The resulting 2,5-dichloro-3-thionobenzoyl chloride 5 was used for the next step without further purification. To a stirred and cooled (5-10 °C) solution of ethyl 3-(N,N-dimethylamino)acrylate (4.3 g, 30 mmol) and triethylamine(5.1 g, 51 mmol) in dry benzene (50 mL) was added dropwise a solution of 5 in dry benzene (20 mL). The resulting mixture was refluxed at 85 °C for 2 h, then cooled to room temperature, and washed with water(3 × 2 mL). The organic layer was separated, dried over MgSO4 and the solvent was then evaporated to dryness to obtain the desired product 6. A stirred solution of 6 in dichloromethane(50 mL) was treated dropwise with cyclopropylamine (2.85 g, 50 mmol) at 2-4 °C. The resulting mixture was then stirred at 25 °C for 24 h. The solvent was evaporated and the residue was soaked with hexane to obtaina yellow precipitate product 7. Sodium hydride (0.8 g,17.5 mmol, 55%) in dry THF (60 mL) was added to the pure 7. The reaction mixture was stirred at room temperature for 30 min. Then, the temperature was increased to 60°C for 3 h. The solvent was evaporated, and the residual white precipitate 8 was washed with water and dried. The product crystallized from the CHCl3/ethanol mixture(1:2).11
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