* 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.
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 9, p. 1153 - 1156
2
[ 50868-73-0 ]
[ 133841-05-1 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 9, p. 1153 - 1156
3
[ 5345-42-6 ]
[ 50868-73-0 ]
Yield
Reaction Conditions
Operation in experiment
97%
With hydrogen In ethanol at 20℃; for 24 h;
Example A2; a) Preparation of intermediate 3; l-methoxy-3-methyl-2-nitro-benzene (25g, 149.7 mmoles) was dissolved in EtOH (100ml). 10percent Pd/C (2.5 g) was added and the mixture was hydrogenated for 24 hours atroom temperature after which period it was filtered on celite. The mixture wasevaporated. Yield : 20.02 g (97percent) of intermediate 3 (CI-MS : 138 ([M+H]+).
Reference：
[1] New Journal of Chemistry, 2006, vol. 30, # 2, p. 168 - 176
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 6, p. 3309 - 3320
[3] Organic letters, 2000, vol. 2, # 3, p. 277 - 280
[4] Patent: WO2006/15985, 2006, A1, . Location in patent: Page/Page column 54-55
[5] Journal of the Chemical Society, 1926, p. 1425
[6] Journal of the Chemical Society, 1923, vol. 123, p. 2989[7] Journal of the Chemical Society, 1924, vol. 125, p. 1305
[8] Journal of the Chemical Society, 1923, vol. 123, p. 1272
[9] Journal of the Chemical Society, 1936, p. 319,321
[10] Journal of the American Chemical Society, 1941, vol. 63, p. 535
[11] Journal of Organic Chemistry, 1961, vol. 26, p. 2310 - 2316
[12] Journal of Organic Chemistry, 1967, vol. 32, p. 1479 - 1483
[13] Analytical Chemistry, 1992, vol. 64, # 8, p. 837 - 842
[14] Organic Letters, 2010, vol. 12, # 8, p. 1732 - 1735
Reference：
[1] Journal of the Chemical Society, 1923, vol. 123, p. 2989[2] Journal of the Chemical Society, 1924, vol. 125, p. 1305
[3] Journal of the Chemical Society, 1923, vol. 123, p. 1272
[4] Journal of Organic Chemistry, 1961, vol. 26, p. 2310 - 2316
[5] Journal of Organic Chemistry, 1967, vol. 32, p. 1479 - 1483
6
[ 68978-27-8 ]
[ 50868-73-0 ]
Reference：
[1] Journal of the Chemical Society, 1923, vol. 123, p. 2989[2] Journal of the Chemical Society, 1924, vol. 125, p. 1305
7
[ 861304-53-2 ]
[ 50868-73-0 ]
Reference：
[1] Journal of the Chemical Society, 1923, vol. 123, p. 2989[2] Journal of the Chemical Society, 1924, vol. 125, p. 1305
8
[ 861304-52-1 ]
[ 50868-73-0 ]
Reference：
[1] Journal of the Chemical Society, 1923, vol. 123, p. 2989[2] Journal of the Chemical Society, 1924, vol. 125, p. 1305
9
[ 100-84-5 ]
[ 50868-73-0 ]
Reference：
[1] Journal of the Chemical Society, 1923, vol. 123, p. 2989[2] Journal of the Chemical Society, 1924, vol. 125, p. 1305
10
[ 108-39-4 ]
[ 50868-73-0 ]
Reference：
[1] Journal of the Chemical Society, 1923, vol. 123, p. 1272
11
[ 5345-42-6 ]
[ 644961-69-3 ]
[ 50868-73-0 ]
Reference：
[1] Journal of the Chemical Society, 1926, p. 1425
12
[ 50868-73-0 ]
[ 38197-43-2 ]
Reference：
[1] European Journal of Organic Chemistry, 2013, # 20, p. 4399 - 4404
[2] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 4, p. 675 - 680
[3] Journal of the American Chemical Society, 1939, vol. 61, p. 2115,2118
[4] Journal of the Chemical Society, 1936, p. 319,321
[5] Journal of the Chemical Society, 1925, vol. 127, p. 498
[6] Journal of Organic Chemistry, 1961, vol. 26, p. 2310 - 2316
[7] Analytical Chemistry, 1992, vol. 64, # 8, p. 837 - 842
13
[ 50868-73-0 ]
[ 29578-83-4 ]
Reference：
[1] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[2] Chemistry - A European Journal, 2005, vol. 11, # 3, p. 951 - 959
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[4] Patent: WO2007/147251, 2007, A1,
[5] Patent: WO2008/124582, 2008, A1,
14
[ 50868-73-0 ]
[ 22061-78-5 ]
Reference：
[1] European Journal of Organic Chemistry, 2013, # 20, p. 4399 - 4404
15
[ 544-92-3 ]
[ 50868-73-0 ]
[ 53005-44-0 ]
Reference：
[1] Synthesis, 1999, # 12, p. 2045 - 2048
With hydrogen;palladium 10% on activated carbon; In ethanol; at 20℃; for 24h;
Example A2; a) Preparation of intermediate 3; l-methoxy-3-methyl-2-nitro-benzene (25g, 149.7 mmoles) was dissolved in EtOH (100ml). 10% Pd/C (2.5 g) was added and the mixture was hydrogenated for 24 hours atroom temperature after which period it was filtered on celite. The mixture wasevaporated. Yield : 20.02 g (97%) of intermediate 3 (CI-MS : 138 ([M+H]+).
Stage #1: 2-methoxy-6-methylbenzeneamine With hydrogenchloride; sodium nitrite In water at 0℃; for 1h;
Stage #2: With potassium iodide In water at 25℃; for 12h; Further stages.;
With sulfuric acid Diazotization.Erhitzen der Diazoniumsalz-Loesung mit KI auf dem Dampfbad;
Multi-step reaction with 2 steps
1: NaNO2; H2SO4
2: KI
Stage #1: 2-methoxy-6-methylbenzeneamine With hydrogenchloride; sodium nitrite In water at 0℃; for 3h;
Stage #2: With potassium iodide In water at 0 - 20℃; for 15h;
With trimethylbenzylammonium bromide; calcium carbonate In methanol; dichloromethane at 20℃; for 1h;
6
2-Methoxy-6-methylaniline (100 mg, 0.73 mmol, 1 eq) is dissolved in a mixture of 10 ml of dichloromethane and 4 ml of methanol. After the addition of 284.7 mg (0.73 mmol, 1 eq) of BTMBr3 and 292 mg (292 mmol) of calcium carbonate, the mixture is stirred at room temperature for one hour. The calcium carbonate is subsequently filtered off, and 10 ml of water is added. The hydrophilic and lipophilic phases are separated, and the water phase is extracted four times with ether. The combined organic extracts are dried over magnesium sulfate, filtered, and the solvent is removed in vacuum on a rotary evaporator. Purification of the product was not necessary (quantitative yield, 157 mg). C8H10BrNO; MW 215/217; 1H-NMR (CDCl3): δ 6.83-6.82 (m, 1H), 6.77 (d, J=1.9 Hz, 1H), 3.81 (s, 3H), 2.12 (s, 3H); 13C-NMR (CDCl3): δ 147.5, 133.4, 125.1, 123.8, 111.5, 109.0, 55.8, 17.0; IR: 3463, 3373, 2973, 1594, 1486, 1409 1/cm; MS (ESI): 216-218 (M+H)+
98%
Stage #1: 2-methoxy-6-methylbenzeneamine With bromine In methanol; acetic acid at 0℃;
Stage #2: With sodium hydroxide In diethyl ether; water
A1.a
2-METHOXY-6-METHYLBENZENAMINE (12.12 g) was dissolved in 100 ml OF MEOH and 10 ml of HOAC. Temperature was lowered to 0°C. A solution of 14.12 g BRS in 50 ml of MEOH was added with carefull temperature-control. After addition, the solvents were evaporated and the residue was dissolved in 300 ml of diethyl ether and 100 ml of 2M NAOH. The layers were separated. The ether-layer was dried (NACL (saturated) and NA2SO4), filtered and concentrated. Yield: 18.68 g of intermediate 1 (4-bromo-2- methoxy-6-methylbenzenamine) (98%).
91%
Stage #1: 2-methoxy-6-methylbenzeneamine With bromine; acetic acid In methanol at 0℃;
Stage #2: With sodium hydroxide; water
26.A
Step A: 4-bromo-2-methoxy-6-methyl-aniline To an ice-water cooled solution of 2-methoxy-6-methylaniline (10 g, 72.9 mmol) in 30 mL of methanol and 10 mL of acetic acid was added dropwise bromine (3.75 mL, 72.9 mmol). The reaction mixture was allowed to stand for overnight. The solvent was removed under reduced pressure and the residue was suspended in 60 mL of 1N NaOH and extracted with ethyl acetate and dried over sodium sulfate and evaporated to dryness to give reddish crude product, which was recrystallized from hexane to give pure product (14.3 g, 91%).
87%
With bromine; acetic acid In methanol for 2h; cooling;
87%
Stage #1: 2-methoxy-6-methylbenzeneamine With bromine; acetic acid In methanol at 0℃; for 2h;
Stage #2: With sodium hydroxide In water
16
[0171] 2-Methoxy-6-methyl phenylamine (lOg, 72.9 mmol) was set stirring in methanol (30 mL) and acetic acid (10 mL) at 0 °C. Bromine (3.73 mL, 72.9 mmol) was dissolved in acetic acid (15 mL) and added dropwise to the reaction. The reaction was stirred for 2 hours and the solvent was removed under reduced pressure. The resulting residue was basified with IN NaOH and partitioned with EtOAc. The organic layer was dried over anhydrous Na2SC>4. The solvent was removed under reduced pressure and the product was purified by column chromatography (20% EtOAc/Hexanes) to afford a red-brown solid (6.86 g, 87%). *H NMR (300 MHz, CDC13): 5 6.87 (d, 1H), 6.81 (d, 1H), 3.85 (s, 3H), 2.16 (s, 3H).
81%
With bromine; acetic acid In methanol at 0 - 20℃; for 3.5h;
In a 100 mL round bottom flask, 2-methoxy-6-methyl-phenyl amine (4.54 g, 33.16 mmol) was dissolved in 15 mL MeOH and 5 mL acetic acid. The flask was cooled to 0 0C. Bromine (1.7 mL, 33.16 mmol) in 5 mL acetic add was added to the reaction dropwise (over 30 minutes). The reaction mixture was stirred at 0 0C for 2 hours, then was warmed up to room temperature for 1 hour. The reaction mixture was concentrated down. IN NaOH was added to neutralize the reaction at 0 0C. Ethyl acetate was added to extract the reaction mixture. The organic layer was concentrated after drying over anhydrous sodium sulfate to give a dark brown solid (5.8 g, 81%). LC-MS shows 218.0 (M+l). 1H NMR (300 MHz, CDCb): δ 6.88(S, 1 H), 6.81 (s, 1 H), 3.84 (s, 3 H), 2.11 (s, 3 H).
81%
With bromine; acetic acid In methanol at 0℃; for 4h;
H.1 HI, 4-Bromo-2-methoxy-6-methyl-phenylamine
HI, 4-Bromo-2-methoxy-6-methyl-phenylamine To a stirred solution of 2-methoxy-6-methylaniline (15.44 g, 113 mmol) in MeOH (30 mL) and acetic acid (20 mL) at 0 °C was added a solution of bromine (5.80 mL, 113 mmol) in acetic acid (20 mL) dropwise. After half of the bromine was added the reaction mixture had solidfied due to precipitation. Additional acetic acid (30 mL) was added and stirring continued. After addition was complete the reaction allowed to stir for 4 hrs. The reaction mixture was filtered to give a light brown filter cake that was washed with additional acetic acid (30 mL) and then isohexanes (50 mL). The solid was in EtOAc (300 mL) and then washed with NaOH (2M, 200 mL). The organics were washed with brine (200 mL), dried over magnesium sulfate, filtered and solvent removed in vacuo to give 4-bromo-2-methoxy-6-methyl-phenylamine (20.14g, 81% yleld). [MH]+ = 216/218
80%
With bromine; acetic acid In methanol for 2h;
53%
With bromine In methanol; acetic acid at 0 - 20℃; for 2h;
53%
With bromine; acetic acid In methanol at 0 - 20℃; for 2h;
68 4.2.68 4-Bromo-2-methoxy-6-methylaniline (17b)
To a solution of 2-methoxy-6-methylaniline (25.0 g, 182 mmol) in acetic acid (30 mL) and methanol (60 mL) was added a solution of bromine (9.34 mL, 182 mmol) in acetic acid (60 mL) at 0 °C, and the mixture was stirred at room temperature for 2 h. The precipitate was collected by filtration, washed with diethyl ether and dissolved in ethyl acetate and saturated aqueous sodium hydrogen carbonate. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine and concentrated in vacuo to give the title compound (20.7 g, 53%) as a brown solid. MS calcd: 215; Found: 216 (M+H). 1H NMR (CDCl3) δ 2.14 (3H, s), 3.83 (3H, s), 6.80 (1H, s), 6.84 (1H, s).
44%
With bromine In methanol at 20℃; for 8h;
17
Bromine (47.1 mL, 0.92 mol) was added dropwise to a solution of 2-methoxy-6-methylaniline (125 g, 0.91 mol) in methanol (1.0 L) at room temperature. The reaction mixture was stirred for 8 h. The reaction mixture was concentrated in vacuo, and combined with ethyl acetate (500 mL) . The precipitate was collected by filtration and washed with ethyl acetate and diethyl ether. The resultant was dissolved in water (400 mL) and ethyl acetate (350 mL) , and neutralized with saturated sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate (200 mL) . The organics were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was recrystallized from ethyl acetate/λ-hexanes mixture (4:1, 500 mL) to give the title compound as purple crystals (87.6 g, 44%) .1H NMR (CDCl3) δ 2.14 (s, 3H), 3.72 (s, 2H), 3.83 (s, 3H), 6.79 (d, J = 2.1 Hz, IH), 6.84 (d, J = 2.1 Hz, IH). MS Calcd.: 215; Found: 216 (M+H) .
40%
With N-Bromosuccinimide In acetonitrile at 20℃; for 3h;
26%
With N-Bromosuccinimide In acetonitrile at 145℃; for 0.25h; Microwave;
To 2-methoxy-6-methyl-phenylamine (10.0 g) dissolved in acetonitrile (200 mL) was added N-bromosuccinimide (14.3 g) and the reaction mixture was heated to 145°C for 15 minutes in a sealed microwave process vessel. The crude mixture was filtered through Celite, diluted with diethyl ether (200 mL) and washed with sodium hydroxide (2 M, 2x 100 mL) and brine (lx 100 mL). The organic phase was dried over magnesium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 3.4 g (26%) of the title compound as a black solid. 1H NMR (500 MHz, DMSO-d6): 2.06 (s, 3H), 3.77 (s, 3H), 4.55 (s, 2H), 6.78 (d, 1H), 6.82 (d, 1H).
Stage #1: 2-methoxy-6-methylbenzeneamine With bromine; acetic acid at 20℃; for 2h;
Stage #2:
Stage #3: In methanol
20.1
2-methoxy-6-methylaniline (24.2 g, 182 mmol) was dissolved in MeOH (81 rnL) and acetic acid (27 rnL) and a solution of bromine (28 g, 182 mmol) in acetic acid (81 mL) was added dropwise. The reaction was allowed to stand at rt for 2 h and concentrated to remove solvents. The crude product was recrystallized from hexanes to give 36 g of 4-bromo-2-methoxy-6-methylaniline as a brown solid.
With bromine; acetic acid In methanol at 20℃; for 2h;
16.1
Step 1. 4-bromo-2-methoxy-6-methylaniline: 2-methoxy-6-methylaniline (24.2 g, 182 mmol) was dissolved in MeOH (81 niL) and acetic acid (27 niL) and a solution of bromine (28 g, 182 mmol) in acetic acid (81 mL) was added dropwise. The reaction was allowed to stand at rt for 2 h and concentrated to remove solvents. The crude product was recrystallized from hexanes to give 36 g of 4-bromo-2- methoxy-6-methylaniline as a brown solid.
With potassium carbonate; mono(N,N,N-trimethylbenzenaminium) tribromide In methanol; dichloromethane at 20℃; for 1h;
1.2.0.i
To a solution of 2-methoxy-6-methylaniline (13.47 g, 98.3 mmol, 1.0 eq.) in DCM (1.3 L) and MeOH (520 mL) is added benzyltrimethylammonium tribromide (38.3 g, 98.3 mmol, 1.0 eq.) and calcium carbonate (39.3 g, 393.2 mmol, 4.0 eq.). The reaction mixture is stirred at r.t. for 1h. The solid is filtered and washed with DCM. The filtrate is washed twice with water. The combined aqueous layers are extracted twice with Et2O. The combined organic phases are dried over anhydrous Na2SO4, filtered, concentrated in vacuo to afford the expected product. LCMS: MW (calcd): 215; m/z MW (obsd): 216-218 (M+H).
With caesium carbonate; mono(N,N,N-trimethylbenzenaminium) tribromide In methanol; dichloromethane at 20℃; for 1h;
2.12.i Step i)
j0270j To a solution of 2-methoxy-6-methylaniline (13.47 g, 98.3 mmol, 1.0 eq.) in DCM (1.3 L) and MeOH (520 mL) is added benzyltrimethylammonium tribromide (38.3 g, 98.3 mmol, 1.0 eq.) and calcium carbonate (39.3 g, 393.2 mmol, 4.0 eq.). The reaction mixture is stirred at r.t. for lh. The solid is filtered and washed with DCM. The filtrate is washed twice with water. The combined aqueous layers are extracted twice with Et20. The combined organic phases are dried over anhydrous Na2504, filtered, concentrated in vacuo to afford the expected product. LCMS: MW (calcd): 215; mlz MW (obsd): 216-218 (M+H)..
With bromine; acetic acid
1
Bromomethoxytoluene (2) was prepared according to Chan et al; J. Med. Chem. (2001), 44, 1866
With sodium dithionite; sodium hydrogencarbonate In tert-butyl methyl ether; water at 20℃; for 16h;
3.3.1
Example 3.1 : 4-( 1 ,2,2,3 ,3 ,3-hexafluoro- 1 -trifluoromethylpropyl)-2-methoxy-6-methyl- phenylamine; To a solution of 2-methoxy-6-methylphenylamine (8.23 g, 60 mmol) in a mixture of water (60 ml) and tert-butyl methyl ether (60 ml) was added, successively 2-iodononafluorobutane (24.9 g, 11.86 ml, 72 mmol), sodium hydrosulfite (15.29 g, 72 mmol), sodium hydrogen carbonate (6.05 g, 72.0 mmol) and tetrabutyl ammonium hydrogen sulfate ("TBAHS") (2.24 g, 6.60 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The mixture was filtered and the filtrate was extracted twice with tert-butyl methyl ether. The combined organic phases were washed with aqueous hydrochloric acid (IN), dried over sodium sulfate and concentrated to give 4-(l,2,2,3,3,3- hexafluoro-l-trifluoromethylpropyl)-2-methoxy-6-methylphenylamine which was used without further purification. LC-MS (Method 2): RT = 2.05, [M+H]+ = 356.
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;
Synthesis of Intermediates 5 (8)
General procedure: To a mixture of benzoic acids 4 (7) (4 mmol),1-ethyl-3-(3-dimethyllaminopropyl) carbodiimide hydrochloride (4.8 mmol) and N-hydroxybenzotrizole (0.48 mmol) wereadded amines (4.8 mmol) at room temperature. The reaction mixture was stirredfor overnight and washed with water successively. The organic layer was driedover anhydrous sodium sulfate. Then the solvent was removed in vacuo to affordcrude compounds 5 (8).
N,N'-bis(2-methoxy-6-methylphenyl)-1,7-dibromoperylene-3,4,9,10-tetracarboxydiimide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
55%
With acetic acid In 1-methyl-pyrrolidin-2-one at 120℃; for 96h; Inert atmosphere;
1,7-dibromoperylene-3,4,9,10- tetracarboxylic dianhyderide (1,7-dibromoperylene-3,4,9,10- tetracarboxylic dianhyderide) 8g (0.0145mol), 2- methoxy-6-methylaniline (2-methoxy-6-methylaniline) 8.28g (0.0467mol), acetic acid (acetic acid) to 4.6ml NMP (N-Methyl-2-pyrrolidone) into a 100ml nitrogen gas at 120°C It is refluxed for 96 hours . When the reaction terminated, the reaction mixture was precipitated slowly poured into 1000ml of distilled water, the resulting precipitate The vacuum filtration. Until pH 7, then washed with water several times with distilled water and dried in a vacuum oven. The dried product MC (methylene chloride, CH2Cl2) was purified using a column, a bromine value is substituted with two bromine precursor and more Hwandoen a precursor were obtained respectively. The final product was characterized by about 55% with yield 4.398g.
With 1-methyl-pyrrolidin-2-one; acetic acid at 120℃; for 96h; Inert atmosphere;
2.2.2. N,N'-bis(R1)-1,7-dibromoperylene-3,4,9,10-tetracarboxydiimide: terminal-position substitution
Crude 1,7-dibromoperylene-3,4,9,10-tetracarboxydiimide (8.00 g, 14.55 mmol), R1-NH2 (45.00 mmol), acetic acid (4.60 ml) and N-methyl-2-pyrrolidone (NMP; 100 ml) were mixed and heated to 120 °C under nitrogen atmosphere for 96 h. Water was added to the mixture and the resulting precipitate was collected by suction filtration. The crude product was washed with water and dried under reduced pressure. The crude product was purified bycolumn chromatography in silica gel using CH2Cl2 as an eluent. Three bands were collected. The first band contained a small amount of tribrominated diimide, the second band contained the dibrominated diimide, and the third contained the monobrominated diimide. Detailed structural analysis was conducted after the next step. To obtain the PI-series, 2,6-diisopropylaniline was used as R1-NH2 and to obtain PM-series, 2-methoxy-6-methylaniline was used.
5-chloro-7-((2-methoxy-6-methylphenyl)amino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With sodium bicarbonate
5.a (5a)
(5a) Synthesis of 5-chloro-7-((2-methoxy-6-methylphenyl)amino)pyrazolo[1,5-a]pyrimidine-2-carboxylic acid ethyl ester A solution of 5,7-dichloropyrazolo[1,5-a]pyrimidine-2-carboxylic acid ethyl ester (CAS No. 1232224-62-2) (8 g) and 2-methoxy-6-methylaniline (CAS No. 50868-73-0) (4.64 g) in NMP (6 mL) was stirred at 150° C. for 4 hours. Ethyl acetate, DMSO and a saturated sodium hydrogen carbonate aqueous solution were added to the reaction mixture, and the organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. The drying agent was filtered off and the filtrate was concentrated under reduced pressure, to obtain a crude product of the title compound (10.98 g). 1H-NMR (500 MHz, CDCl3, mixture of rotamers) δ: 1.46 (t, J=7 Hz, 3H), 2.27 (s, 3H), 3.78 (s, 3H), 4.50 (q, J=7 Hz, 2H), 5.66 (s, 1H), 6.88 (d, J=8 Hz, 1H), 6.95 (d, J=8 Hz, 1H), 6.99 (s, 1H), 7.31 (t, J=8 Hz, 1H), 7.80 (s, 1H). Mass spectrum (ESI) m/z: 361 (M+H)+
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