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[ CAS No. 32407-11-7 ] {[proInfo.proName]}

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Chemical Structure| 32407-11-7
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Product Details of [ 32407-11-7 ]

CAS No. :32407-11-7 MDL No. :MFCD11647707
Formula : C7H7Cl2NO Boiling Point : -
Linear Structure Formula :- InChI Key :GNFMBCBDTFAEHM-UHFFFAOYSA-N
M.W : 192.04 Pubchem ID :13178651
Synonyms :

Calculated chemistry of [ 32407-11-7 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.36
TPSA : 35.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.9
Log Po/w (XLOGP3) : 2.8
Log Po/w (WLOGP) : 2.59
Log Po/w (MLOGP) : 2.33
Log Po/w (SILICOS-IT) : 2.39
Consensus Log Po/w : 2.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.13
Solubility : 0.142 mg/ml ; 0.000737 mol/l
Class : Soluble
Log S (Ali) : -3.2
Solubility : 0.122 mg/ml ; 0.000635 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.4
Solubility : 0.0763 mg/ml ; 0.000397 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.43

Safety of [ 32407-11-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 32407-11-7 ]

* 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 [ 32407-11-7 ]

[ 32407-11-7 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 17742-69-7 ]
  • [ 32407-11-7 ]
YieldReaction ConditionsOperation in experiment
57.9% With tin(II) chloride dihdyrate; ethanol; In ethanol; at 20 - 80℃; for 1.08333h; To a stirred solution of 24 (1.5 g, 6.76 mmole) in EtOH (25 mL) was added SnC122H20 (7.62 g, 33.77 mmole) portion-wise over a period of5 mm. at rt. The reaction mixture was heated at 80 for 1 hr, then cooled to rt. This reaction was repeated 3 additional times, and all of the crude reaction mixtures were combined and poured into ice-water. The resulting mixture was basified to pH = 12 with 2N NaOH solution, then filtered through a pad of Celite. The aqueous filtrate was extracted with EtOAc (2 x 500 mL). The combined organic extracts were dried over Na2SO4 andevaporated in vacuo to give 3.0 g (57.9% yield) of product as a brown solid. LCMS m/z192 [M + H - 11, 194 [M+ H +11, 196 [M + H + 31; (99.1% purity). ?H NMR (400 MHz, DMSO-d6) oe 6.59 (s, 2H), 5.39 (s, 2H), 3.67 (s, 3H).
With ammonium chloride;zinc; In ethanol; at 20℃;Near reflux; 2. Preparation of 2-CyanobenzothiazolesThe following procedure is for the preparation of 5,7-dichloro-6-hydroxy-2- cyanobenzothiazole. The preparation of 5,7-difluoro-6-hydroxy-2-cyanobenzothiazole followed the same procedure with very similar results.A 5 -L round-bottomed flask was charged with l,3-dichloro-2-methoxynitrobenzene (0.33 moles), ammonium chloride (3.3 moles), and ethanol (1200 mL). Zinc dust (3.3 moles) is added rapidly to the stirred mixture. The reaction mixture warmed to near reflux after several minutes and was then allowed to cool to room temperature. After stirring overnight, the suspension was filtered to remove residual zinc and ammonium chloride. The filtrate was concentrated under reduced pressure and the resulting solid was resuspended in CH2Cl2 (1500 mL). The suspension was filtered and the filtrate concentrated under reduced pressure to give the substituted aniline as a white solid (0.33 moles).IA Y = Cl 1H NMR (W MHZ, CDCl3): 8 6.601 (s, 2H), 3.811 (s, 3H), 3.6-3.7 (broad s, 2H) IB Y = F 1H NMR ^OO MHZ1 CDCI3): delta 6.22 (m, 2H), 3.860 (s, 3H), 3.6-3.7 (broad s, 2H)
  • 2
  • [ 32407-11-7 ]
  • [ 70439-96-2 ]
YieldReaction ConditionsOperation in experiment
90% With N-chloro-succinimide In toluene at 80℃; for 1h;
  • 3
  • [ 32407-11-7 ]
  • [ 421766-14-5 ]
YieldReaction ConditionsOperation in experiment
80% With N-chloro-succinimide In toluene at 80℃; for 1h;
Multi-step reaction with 3 steps 2: aqueous potassium chlorate; hydrochloric acid / 0 °C 3: aq. NaOH solution
  • 4
  • [ 32407-11-7 ]
  • [ 32770-89-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 5
  • [ 32407-11-7 ]
  • 4-methoxy-2,3,3',4',5,6-hexachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 6
  • [ 32407-11-7 ]
  • 4-methoxy-2,2',3,3',5,6-hexachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 7
  • [ 32407-11-7 ]
  • 2',4-dimethoxy-2,3,3',4',5-pentachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 8
  • [ 32407-11-7 ]
  • 4,4'-dimethoxy-2,2',3,3',5-pentachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 9
  • [ 32407-11-7 ]
  • 3',4-dimethoxy-2,2',3,4',5-pentachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 10
  • [ 32407-11-7 ]
  • 4,4'-dimethoxy-2,3,3',5,5'-pentachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 11
  • [ 32407-11-7 ]
  • 3',4-dimethoxy-2,3,4',5,5'-pentachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 12
  • [ 32407-11-7 ]
  • 4-methoxy-2,2',3,3',4',5,5',6-octachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 13
  • [ 32407-11-7 ]
  • 4-methoxy-2,2',3,3',4',5,5',6'-octachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 14
  • [ 32407-11-7 ]
  • 4,4'-dimethoxy-2,2',3,3',5,5',6-heptachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
Multi-step reaction with 2 steps 1: 80 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 15
  • [ 32407-11-7 ]
  • 3',4-dimethoxy-2,2',3,4',5,5',6-heptachlorobiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 90 percent / NCS / toluene / 1 h / 80 °C 2: 120 °C
  • 17
  • [ 32315-10-9 ]
  • [ 32407-11-7 ]
  • [ 58840-69-0 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane for 24h; Heating / reflux; 134.2 Step-2. A solution of the above aniline (2.12 g) and triphosgene (3.28 g) in dioxane (20 mL) was refluxed for 24 hours. The solvent was evaporated and the product was used for next step without further purification.
  • 18
  • [ 24424-99-5 ]
  • [ 32407-11-7 ]
  • [ 147494-24-4 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; diethyl ether; hexane; ethyl acetate 20.b b. b. N-(tert-Butoxycarbonyl)-3,5-dichloro-4-methoxyaniline A solution of 3,5-dichloro-4-methoxyaniline (7.76 g, 40.4 mM) and di-tert-butyldicarbonate (17.6 g, 80.8 mM) in tetrahydrofuran (38 mL) was stirred under nitrogen at room temperature for 66 hr. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate which was washed successively with 1N sodium hydroxide, brine, and water and then dried (MgSO4), filtered and concentrated to obtain a brown oil (21 g) which slowly crystallized. This material was slurried in hexane and then filtered to separate the desired product as white crystals (7.5 g). An additional quantity of product (2.3 g, total yield=83%) was obtained by chromatography of the residue obtained by concentration of the slurry liltrate over silica gel (eluant: hexane/diethyl ether, 85/15). Recrystallization of a portion of this material from diethyl ether/hexane provided an analytical sample as white crystals, mp 115°-116° C.; MS(CI): 292 (M+H). Analysis for C12 H15 Cl2 NO3 Calculated: C, 49.33; H, 5.17; N, 4.79 Found: C, 49.38; H, 5.18; N, 4.74
  • 19
  • tin(II)chloride dihydrate [ No CAS ]
  • [ 17742-69-7 ]
  • [ 32407-11-7 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In ethanol; a. 3,5-Dichloro-4-methoxyaniline A stirred mixture of <strong>[17742-69-7]2,6-dichloro-4-nitroanisole</strong> (4.6 g, 21 mM) and tin(II) dichloride dihydrate (23.4 g, 104 mM) in ethanol (72 mL) was refluxed for 3 hr. After cooling to room temperature, the reaction mixture was poured into ice water which was then treated with 2N sodium hydroxide until the solution became basic. The resulting mixture was filtered through diatomaceous earth and the liltrate was extracted with ethyl acetate. The combined ethyl acetate extracts were dried (MgSO4), filtered and concentrated to obtain (3.33 g, 83.7%) the title compound as a yellow-brown solid, mp 80-81 C.; MS(CI): 192 (M+H).
  • 20
  • [ 108-23-6 ]
  • [ 32407-11-7 ]
  • isopropyl N-(3,5-dichloro-4-methoxyphenyl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91.8% With N,N-diethylaniline In benzene 1 Preparation of isopropyl N-(3,5-dichloro-4-methoxyphenyl)carbamate according to Procedure (a): EXAMPLE 1 Preparation of isopropyl N-(3,5-dichloro-4-methoxyphenyl)carbamate according to Procedure (a): 3,5-Dichloro-4-methoxyaniline (1.8 g) and diethylaniline (1.5 g) were dissolved in benzene (20 ml). To the resultant solution was dropwise added isopropyl chloroformate (1.2 g) in 5 minutes under ice-cooling. After being allowed to stand at room temperature for 12 hours, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a mixture of benzene and tetrahydrofuran as the eluent to give isopropyl N-(3,5-dichloro-4-methoxyphenyl)carbamate (Compound No. 2) (2.4 g) in a yield of 91.8%. M.P., 107.5°-108° C. Elementary analysis: Calcd. for C11 H13 Cl2 NO3: N, 5.02%; C, 47.38%; H, 4.69%; Cl, 25.44%. Found: N, 5.11%; C, 47.52%; H, 4.76%; Cl, 25.49%.
91.8% With N,N-diethylaniline In benzene 1 EXAMPLE 1 EXAMPLE 1 Preparation of isopropy N-(3,5-dichloro-4-methoxyphenyl)carbamate according to Procedure (a): 3,5-Dichloro-4-methoxyaniline (1.8 g) and diethylaniline (1.5 g) were dissolved in benzene (20 ml). To the resultant solution was dropwise added isopropyl chloroformate (1.2 g) in 5 minutes under ice-cooling. After being allowed to stand at room temperature for 12 hours, the reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a mixture of benzene and tetrahydrofuran as the eluent to give isopropyl N-(3,5-dichloro-4-methoxyphenyl)carbamate (Compound No. 2) (2.4 g) in a yield of 91.8%. M.P., 107.5°-108° C. Elementary analysis: Calcd. for C11 H13 Cl2 NO3: N, 5.02%; C, 47.38%; H, 4.69%; Cl, 25.44%. Found: N, 5.11%; C, 47.52%; H, 4.76%. Cl, 25.49%.
  • 21
  • Acetylsalicylic acid chloride [ No CAS ]
  • [ 32407-11-7 ]
  • [ 50-78-2 ]
  • [ 55411-43-3 ]
YieldReaction ConditionsOperation in experiment
64% With hydrogenchloride; thionyl chloride In sodium hydroxide; <i>N</i>,<i>N</i>-dimethyl-aniline; acetone 6 Preparation of 3',5'-dichloro-2-hydroxy-4'-methoxybenzanilide EXAMPLE 6 SPC15 Preparation of 3',5'-dichloro-2-hydroxy-4'-methoxybenzanilide Acetylsalicylic acid (1.8 g.) was converted to its acid chloride by conventional method using thionyl chloride and dissolved in acetone (30 ml.). 4-Amino-2,6-dichloroanisole (2.13 g.) with N,N-dimethylaniline (1.27 ml.) was dissolved in acetone (25 ml.) to which, with stirring in the cold at 0°-10° C., the above acetone solution of acetylsalicyloyl chloride was added dropwise over 20-30 minutes. Reaction continued for 1-2 hours, then the solution was evaporated to dryness under reduced pressure, the residue being put in sodium hydroxide solution and gently agitated for 1-2 hours for cleavage of the acetyl group. After reaction was complete the solution was made acidic by the addition of 2 N hydrochloric acid and the precipitate which formed was collected by filtration and recrystallized from aqueous acetone to give needle-like crystals (2.0 g.) of 3',5'-dichloro-2-hydroxy-4'-methoxybenzanilide. Yield 64%. The melting point of the product is 226°- 228° C.
  • 22
  • [ 17742-69-7 ]
  • [ 821-48-7 ]
  • [ 32407-11-7 ]
  • [ 204634-62-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In ethyl acetate; butan-1-ol; EXAMPLE 7 1-(3,5-Dichloro-4-methoxyphenyl) piperazine 3,5-Dichloro-4-methoxyaniline, m.p. 77-79, was prepared by the catalytic hydrogenation (10% Pd-C) of <strong>[17742-69-7]2,6-dichloro-4-nitro-anisole</strong> in ethyl acetate at ambient temperature and atmospheric pressure. A mixture of 3,5-dichloro-4-methoxyaniline (16.0g) and bis-(2-chloroethyl)amine hydrochloride (14.77g) in n-butanol (100 ml) was stirred under reflux for 48 hr. Anhydrous potassium carbonate (11.45g) was added and the resulting mixture was stirred under reflux for a further 24 hr., then filtered hot.
  • 23
  • [ 32407-11-7 ]
  • [ 1260754-33-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 0.33 h / Inert atmosphere; Reflux 2: 1 h / 140 °C / Inert atmosphere
  • 24
  • [ 32407-11-7 ]
  • [ 1260754-27-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 0.33 h / Inert atmosphere; Reflux 2: 1 h / 140 °C / Inert atmosphere 3: pyridine hydrochloride / 3 h / 195 °C / Inert atmosphere
  • 25
  • [ 32407-11-7 ]
  • [ 1310057-94-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: pyridine / dichloromethane / 0.33 h / Inert atmosphere; Reflux 2: 1 h / 140 °C / Inert atmosphere 3: pyridine hydrochloride / 3 h / 195 °C / Inert atmosphere 4: triethylamine; hydrogen sulfide; pyridine / 20 °C
  • 26
  • [ 32407-11-7 ]
  • [ 1310058-66-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: pyridine / dichloromethane / 0.33 h / Inert atmosphere; Reflux 2: 1 h / 140 °C / Inert atmosphere 3: pyridine hydrochloride / 3 h / 195 °C / Inert atmosphere 4: triethylamine; hydrogen sulfide; pyridine / 20 °C 5: methanol / 20 - 80 °C
  • 27
  • [ 32407-11-7 ]
  • C11H4Cl2N2O3S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: pyridine / dichloromethane / 0.33 h / Inert atmosphere; Reflux 2.1: 1 h / 140 °C / Inert atmosphere 3.1: pyridine hydrochloride / 3 h / 195 °C / Inert atmosphere 4.1: triethylamine; hydrogen sulfide; pyridine / 20 °C 5.1: methanol / 20 - 80 °C 6.1: sodium hydroxide; water; methanol / 48 h / 20 °C 6.2: pH 2
  • 28
  • [ 75318-43-3 ]
  • [ 32407-11-7 ]
  • [ 1260754-30-0 ]
YieldReaction ConditionsOperation in experiment
With pyridine In dichloromethane for 0.333333h; Inert atmosphere; Reflux; 1.2 A 2-L three-necked round-bottomed flask was oven-dried and cooled under an argon flow. The flask was charged with l,3-dichloro-2-methoxyaniline (0.33 moles), pyridine (75 mL), and CH2CI2 (550 mL). The appel salt (0.33 moles) was added in portions over 5 minutes causing the solution to reflux. TLC showed the complete disappearance of the aniline after 15 minutes. The reaction mixture was concentrated to an orange solid. The solid was dissolved in 2.5 L of ethyl acetate. The organic solution was washed with type 1 water (2 x 1000 mL) and brine (1000 mL). The washed organic layer was dried over anhydrous Na2SO4 and concentrated to give the appel salt adduct as a solid.2A Y = Cl 1H NMR (400 MHz, CDCl3): δ 7.203 (s, 2H), 3.933 (s, 3H)2B Y = F 1H NMR ^OO MHZ1 CDCI3): δ 6.87 (m, 2H), 4.030 (S, 3H)
  • 29
  • [ 32407-11-7 ]
  • 1-(3,5-dichloro-4-methoxyphenyl)-1H-pyrrole-2,5-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: diethyl ether / 16 h / 20 °C 2: sodium acetate; acetic anhydride / 2 h / 80 °C
  • 30
  • [ 32407-11-7 ]
  • 5,7-dichloro-2’-(3,5-dichloro-4-methoxyphenyl)-7’,7’-dimethyl-3a’,6’,7’,8’,8a’,8b’-hexahydro-1’H-spiro[indoline-3,4’-pyrrolo[3,4-a]pyrrolizine]-1‘,2,3’(2’H)-trione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: diethyl ether / 16 h / 20 °C 2: sodium acetate; acetic anhydride / 2 h / 80 °C 3: ethanol / 1 h / 80 °C
  • 31
  • [ 108-31-6 ]
  • [ 32407-11-7 ]
  • (E)-4-((3,5-dichloro-4-methoxyphenyl)amino)-4-oxobut-2-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
55.5% In diethyl ether at 20℃; for 16h; 4 (E)-4-((3,5-dichloro-4-methoxyphenyl)amino)-4-oxobut-2-enoic acid (26). 2 (1.84 g,18.74 mmole) was added to a stirred solution of 25 (3.60 g, 18.74 mmol) in Et20 (60 mL) ata The reaction mixture was stirred at rt for 16 hr, then filtered. The solid that wascollected was dried in vacuo to give the crude product, which was purified by prep-HPLC to give 3.0 g (55.5% yield) of product as an off-white solid. LCMS m/z 290 [M + H - 11, 292 [M + H +11, 294 [M + H + 31; (99.9% purity). ‘H NMR (400 MHz, DMSO-d6) ö 12.89 (br s, 1H), 10.51 (s, 1H), 7.72 (s, 2H); 6.45 (d, J = 12 Hz, 1H), 6.20 (d, J = 12Hz, 1H), 3.79 (s, 3H), 3.38 (dd, J = 14Hz, J = 6.8 Hz, 1H), 1.09 (dd, J = 14Hz, J = 6.8 Hz, 1H).
  • 32
  • [ 100874-09-7 ]
  • [ 32407-11-7 ]
  • C21H16Cl2N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With potassium <i>tert</i>-butylate; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 110℃; for 12h; Inert atmosphere; Sealed tube;
  • 33
  • [ 1353531-00-6 ]
  • [ 32407-11-7 ]
  • 1-(6-chlorobenzo[d]thiazol-2-yl)-3-(3,5-dichloro-4-methoxyphenyl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With triethylamine In N,N-dimethyl-formamide at 20℃;
  • 34
  • [ 3107-19-5 ]
  • [ 32407-11-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: methanol / 1.5 h / 0 - 20 °C 2: hydrogenchloride; tin(II) chloride dihdyrate / ethanol; 1,4-dioxane / 16 h / 0 - 20 °C
  • 35
  • [ 32407-11-7 ]
  • 4-amino-2,6-dichloro-3,5-dideuteriophenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogen chloride / water-d2 / 30 h / 100 °C 2: boron tribromide / 16 h / 0 - 20 °C
  • 36
  • [ 32407-11-7 ]
  • C13H10(2)H2Cl3N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen chloride / water-d2 / 30 h / 100 °C 2: boron tribromide / 16 h / 0 - 20 °C 3: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 90 °C / Inert atmosphere
  • 37
  • [ 32407-11-7 ]
  • C13H11(2)H2Cl2N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 16 h / 100 °C 4.2: 16 h / 100 °C
  • 38
  • [ 32407-11-7 ]
  • C19H16(2)H2Cl2N6O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 16 h / 100 °C 4.2: 16 h / 100 °C 5.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 5.2: 0.5 h / 0 °C
  • 39
  • [ 32407-11-7 ]
  • 2-(3,5-dichloro-4-((5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)phenyl-2,6-d2)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 16 h / 100 °C 4.2: 16 h / 100 °C 5.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 5.2: 0.5 h / 0 °C 6.1: sodium acetate; acetic acid / 1.5 h / 120 °C
  • 40
  • [ 32407-11-7 ]
  • C13H9(2)H2Cl4N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen chloride / water-d2 / 30 h / 100 °C 2: boron tribromide / 16 h / 0 - 20 °C 3: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 24 h / 90 °C / Inert atmosphere
  • 41
  • [ 32407-11-7 ]
  • C13H10(2)H2Cl3N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 24 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 100 °C 4.2: 100 °C
  • 42
  • [ 32407-11-7 ]
  • C19H15(2)H2Cl3N6O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 24 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 100 °C 4.2: 100 °C 5.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 5.2: 0.5 h / 0 °C
  • 43
  • [ 32407-11-7 ]
  • 2-(3,5-dichloro-4-((4-chloro-5-isopropyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)phenyl-2,6-d2)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 24 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 100 °C 4.2: 100 °C 5.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 5.2: 0.5 h / 0 °C 6.1: sodium acetate; acetic acid / 120 °C
  • 44
  • [ 32407-11-7 ]
  • C13H5(2)H8Cl2N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 16 h / 100 °C 4.2: 16 h / 100 °C
  • 45
  • [ 32407-11-7 ]
  • C19H10(2)H8Cl2N6O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 16 h / 100 °C 4.2: 16 h / 100 °C 5.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 5.2: 0.5 h / 0 °C
  • 46
  • [ 32407-11-7 ]
  • 2-(3,5-dichloro-4-((6-oxo-4-(propan-2-yl-1,1,1,3,3,3-d6)-1,6-dihydropyridazin-3-yl)oxy)phenyl-2,6-d2)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine-6-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 16 h / 100 °C 4.2: 16 h / 100 °C 5.1: hydrogenchloride; sodium nitrite / water / 0.5 h / 0 °C 5.2: 0.5 h / 0 °C 6.1: sodium acetate; acetic acid / 2 h / 120 °C
  • 47
  • [ 32407-11-7 ]
  • C13H4(2)H8Cl3N3O [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogen chloride / water-d2 / 30 h / 100 °C 2: boron tribromide / 16 h / 0 - 20 °C 3: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 90 °C / Inert atmosphere
  • 48
  • [ 32407-11-7 ]
  • C13H5(2)H8Cl2N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: hydrogen chloride / water-d2 / 30 h / 100 °C 2.1: boron tribromide / 16 h / 0 - 20 °C 3.1: potassium carbonate; copper(l) iodide / dimethyl sulfoxide / 16 h / 90 °C / Inert atmosphere 4.1: sodium acetate; acetic acid / 16 h / 100 °C 4.2: 16 h / 100 °C
  • 49
  • [ 32407-11-7 ]
  • C7H5(2)H2Cl2NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogen chloride In water-d2 at 100℃; for 30h; 31.3 Step 3: Example 31d To a solution of Example 31c (5.0 g, 26.0 mmol) in D20 (40 mL) was added DC1 (80 mL, 35% in D20). The reaction mixture was stirred at l00°C for 30 h. The mixture was concentrated in reduced pressure to give the crude desired product Example 31d (5.0 g, yield 99%, D>=99%) as a pink solid which was used for the next step directly. LCMS [M+l]+= 194.0 (1041) ‘HNMR (400 MHz, MeOD) d 3.91 (s, 3H).
  • 50
  • [ 32407-11-7 ]
  • [ 159178-03-7 ]
  • 1-(3,5-dichloro-4-methoxyphenyl)-3-(2,6-dichloropyridin-4-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
49% In tetrahydrofuran at 50℃; for 8h; 4.1.1. Procedure for preparation of compounds 10, 14, 18 General procedure: Compound 3 (1000 mg, 5.35 mmol) was mixed with(CH3)2NHHCl (477 mg, 5.88 mmol), Et3N (1081 mg, 10.70 mmol) inDCM (15 mL), and allowed to stir at room temperature for 8 h. Thenthe mixture was washed with water and extracted with DCM, theextract was combined and washed with saturated NaCl solution,dried over anhydrous MgSO4, filtered, and concentrated in vacuo.The crude product was purified by column chromatography toafford the compound 4 (566 mg, 54 %) as a white solid. Compound 4(500 mg, 2.55 mmol) was mixed with CH3I (543 mg, 3.83 mmol),NaH (184 mg, 7.65 mmol) in dimethyl formamide (DMF, 15 mL) andallowed to stir under ice bath conditions for 2 h. Then the reactionwas quenched with water and extracted with DCM, the extract wascombined and washed with saturated NaCl solutions, then driedover anhydrous MgSO4, filtered, and concentrated. The crudeproduct was purified by column chromatography to afford thecompound 5 (423 mg, 79 %) as a white solid. 80 % Hydrazine hydrate(3012 mg, 60.24 mmol) was mixed with a solution of 5(229 mg, 1.09 mmol) in ethanol (10 mL). The mixture was heated at100 °C for 3 h. Then the mixturewas concentrated andwashed withsaturated NaCl solutions and extracted with DCM. The extract wasdried over anhydrous MgSO4, filtered, and concentrated in vacuo toyield compound 6 as a white solid (204 mg, 91 %).A mixture of 2,6-dichloroisonicotinic acid (1000 mg,5.20 mmol), Et3N (687 mg, 6.80 mmol), in 1,4-dioxane (10 mL) wasallowed to stir at 0 °C and diphenyl phosphoryl azide (1900 mg,6.80 mmol) was added dropwise. Then the mixture was warmed toroom temperature. After the reaction was completed, the mixturewas washed into 1 M NaHCO3 solution and extracted with DCM.The extract was washed with saturated NaCl solution, dried overanhydrous MgSO4, filtered, and concentrated in vacuo. The crudeproduct was purified by column chromatography to afford compound8 (753 mg, 67 %) as a white solid.A solution of 8 (159 mg, 0.74 mmol) in toluene (1 mL) wasrefluxed for 2 h to produce the isocyanate 9. The mixture was cooled to 50 °C, and compound 6 (152 mg, 0.74 mmol) in anhydrousTHF (3 mL) was added, and the mixture was allowed to stir foranother 8 h. Then the reaction mixture was concentrated in vacuo,and the residue was subjected to column chromatography to affordcompound 10 (134 mg, 46 %) as a white solid.
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