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CAS No. : | 383865-57-4 | MDL No. : | MFCD18642707 |
Formula : | C12H15N3O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DOIKFFGWUPLXGA-UHFFFAOYSA-N |
M.W : | 265.33 | Pubchem ID : | 11402861 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.42 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 76.24 |
TPSA : | 88.85 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.68 cm/s |
Log Po/w (iLOGP) : | 2.18 |
Log Po/w (XLOGP3) : | 1.75 |
Log Po/w (WLOGP) : | 1.35 |
Log Po/w (MLOGP) : | 0.75 |
Log Po/w (SILICOS-IT) : | 2.33 |
Consensus Log Po/w : | 1.67 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.83 |
Solubility : | 0.396 mg/ml ; 0.00149 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.23 |
Solubility : | 0.155 mg/ml ; 0.000585 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.93 |
Solubility : | 0.314 mg/ml ; 0.00118 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.84 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With bromine In chloroform for 18 h; Heating / reflux | (2-Methoxy-5-morpholin-4-yl-phenyl)-thiourea (5.0 g, 19 mmol) in chloroform (130 ml) are treated with bromine (960 μl) and the mixture refluxed for 18 hours. After removal of the volatile components in vacuo, the product is recrystallized from THF (2.8 g, 57percent). MS: m/e=266 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With pyridine; In dichloromethane; water; ethyl acetate; at 0 - 20℃; for 1h; | A suspension of <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> (26.5 g, 100 mmol) in dichloromethane (56 ml) and pyridine (56 ml, 700 mmol) is added phenyl chloroformate (15.7 ml, 125 mmol) at 0-5 C. and the reaction mixture is warmed to ambient temperature. After 1 h, water (7.2 ml, 400 mmol) was added and the reaction mixture is heated for 1 h to 45 C. Then ethyl acetate (250 ml) and 2M HCL (125 ml) were added and the organic phase separated. After removal of the solvent and recrystallization from tert.butyl-methyl ether and finally from ethanol the title compound was obtained as white solid (80% yield), mp 166-168 C. MS: m/e=386(M+H+). |
4-Methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine was first reacted with phenyl chloroformate as described for (4-methoxy-7-phenyl-benzothiazol-2-yl)-carbamic acid benzyl ester in WO01/97786 and then with methyl-(4-trifluoromethyl-cyclohexyl)-amine. Usual workup, flash-chromatography (silica, eluent dichloromethane/methanol) and final evaporation of the solvent afforded the title compound as white crystals (96% yield), mp 157-167 C. MS: m/e=473(M+H+). Following the general method of example 1 the compounds of examples 2 to 12 were prepared. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 20℃; for 17.1h; | 20.0 g Pyridine acid (115 mmol) were suspended at RT in 100 ml dichloromethane. 0.5 ml Dimethylformamide (6.5 mmol) was added, and after 0.2 h, 14.9 g oxalyl chloride (10.2 ml, 115 mmol) were added over 2 min. The dropping funnel was rinsed with 4 ml dichloromethane. The brown suspension was stirred at RT for 3 h. Then 200 ml tetrahydrofuran were added causing the acid chloride to partially precipitate. After 0.2 h, 24.3 g aminobenzothiazole (IA) (92 mmol) were added in one portion at RT. Directly afterwards, 56.0 ml N-ethyldiisopropylamine (42 g, 321 mmol) were added over 0.1 h., and the reaction mixture was stirred at RT overnight (17 h). The contents were heated to reflux (60 C.), and 300 ml water were added whilst maintaining ca. constant volume throughout a distillation process until the internal temperature reached 90 C. Once all the water was added, heating was increased to 110 C. and a total of 280 ml of distillate was collected. A further 320 ml water was added in one portion, and the temperature was increased to 120 C. whereby the internal and distillate temperature rose to 70 C. Around 20 ml more solvent was removed, and after 0.1 h, the internal and distillate temperatures reached 90 and 75 C., respectively. The reaction contents were allowed to cool to RT (ca. 1.2 h); then stirring was continued for 1.5 h to complete the precipitation of the product. This product was filtered and washed in 30 ml portions with a total of 150 ml water. Further purification was carried out in conventional manner. Yield: 30.4 g (86% from amine). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonia; In ethanol; water; at 20 - 55℃; for 16h;pH 9 - 10; | The aminobenzothiazole was purified by liberating it from the undried crude HBr-salt. This was dissolved in 450 ml ethanol, diluted with 600 ml water and heated to 55 C. The red solution was basified with 50 ml 25% aqueous ammonia to pH 9-10, forming a suspension which was stirred and allowed to cool to RT overnight (16 h). The product was filtered and washed portionwise with 140 ml 50% aqueous ethanol and then dried for 24 h at 45 C./1 mb. 45.1 g (90%). 1H-NMR: (400 MHz, CDCl3): delta=3.05 (m, 4H), 3.86 (m, 4H), 3.95 (s, 3H), 5.14 (bs, 2H), 6.73 (d, 2H), 6.78 (d, 2H). MS: 266 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | EXAMPLE 8 (4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid tetrahydro-pyran-4-yl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and tetrahydropyran-4-ol, the title compound was obtained as white solid (7% yield). MS: m/e=394(M+H+), mp 187-188 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | EXAMPLE 4 (4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid isobutyl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and isobutanol, the title compound was obtained as yellow crystals (12% yield). MS: m/e=366(M+H+), mp 164-168 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | EXAMPLE 5 (4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid cyclohexyl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and cyclohexanol, the title compound was obtained as white solid (60% yield). MS: m/e=392(M+H+), mp 177-179 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | EXAMPLE 11 (cis/trans)-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid 3-hydroxy-cyclopentyl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and (cis/trans)-cyclopentane-1,3-diol, the title compound was obtained as white solid (42% yield). MS: m/e=394(M+H+), mp 188-189 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | EXAMPLE 3 (4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid 2-methoxy-ethyl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and 2-methoxy-ethanol, the title compound was obtained as off-white solid (52% yield). MS: m/e=368(M+H+), mp 149-152 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | EXAMPLE 9 (rac)-(exo,exo)-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid 5-hydroxy-bicyclo[2.2.1]hept-2-yl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and (rac)-(exo,exo)-bicyclo[2.2.1]heptane-2,5-diol, the title compound was obtained as white solid (10% yield). MS: m/e=420(M+H+), mp 193-194 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | To a solution of <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> (220 mg, 0.83 mmol) in dry tetrahydrofurane (10 ml) at -70 C. is slowly added a solution of tert.butyllithium (1.1 ml of a 1.5 M solution in pentane corresponding to 1.65 mmol) and the remaining suspension slowly warmed to about -30 C. At this time, a solution of 2-[(2-methoxy-ethyl)-methyl-amino]-methyl}-3-methyl-3H-imidazole-4-carboxylic acid phenyl ester (252 mg, 0.83 mmol) in tetrahydrofurane (4 ml) was added and the mixture stirred for 1 h at room temperature. The reaction mixture was treated with saturated aqueous ammonium chloride solution (10 ml) followed by ethyl acetate (20 ml) and the formed precipitate collected. The phases were separated and the aqueous phase extracted three times with ethyl acetate. The combined organic layers were extracted twice with water, dried with magnesium sulfate and evaporated to dryness to yiled anoher batch of raw product. Flash-chromatography on silica (eluent trichloromethane containing 30% of ethyl acetate) yielded the title compound as white solid (31% yield). MS: m/e=475(M+H+), mp 176-178 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | EXAMPLE 6 (tran)s-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid 4-hydroxy-cyclohexyl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and, the title compound was obtained as white foam (14% yield). MS: m/e=408(M+H+), mp 176-179 C. MS: m/e=407.49(M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 - 50℃; for 3h; | EXAMPLE 1 (cis)-2-(3-Acetoxy-cyclopentyl)-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-acetamide; To a solution of (rac)-(cis)-3-(acetyloxy)-cyclopentaneacetic acid (770 mg, 4.1 mmol) and N,N-dimethylformamide (0.01 ml, 0.13 mmol) in dichloromethane (10 ml) were added oxalyl chloride (1.4 ml, 17 mmol) and the resulting solution stirred for 18 h at ambient temperature. After evaporation of the volatile components in vacuo, the residue was taken up in toluene (10 ml) and again evaporated to dryness. The obtained acid chloride was then dissolved in dichloromethane (20 ml) and subsequently treated with N-ethyl-diisopropyl amine (2.5 ml, 15 mmol) and <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> (960 mg, 3.6 mmol). After stirring for 2 h at ambient temperature and another hour at 50 C., the mixture was cooled to room temperature and treated with saturated aqueous sodium hydrogen carbonate (15 ml) and extracted twice with dichloromethane (20 ml each). After drying over magnesium sulphate and evaporation of the solvents, flash chromatography (silica, eluent dichloromethane/ethyl acetate 85:15) afforded (rac)-(cis)-2-(3-acetoxy-cyclopentyl)-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-acetamide as off-white solid. Separation by preparative chiral HPLC (Chiralpack AD, eluent heptane/isopropanol 85:15) afforded the title compound as first eluting isomer. Light yellow solid (4% yield). MS: m/e=434(M+H+), mp 171-172 C.; Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and (rac)-(cis)-acetic acid 3-chlorocarbonylmethyl-cyclopentyl ester, (rac)-(cis)-2-(3-acetoxy-cyclopentyl)-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-acetamide was obtained. Separation by preparative chiral HPLC (Chiralpack AD, eluent heptane/isopropanol 85:15) afforded the tide compound as later eluting isomer. Light yellow crystals (4% yield). MS: m/e=434(M+H+), mp 172-173 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | EXAMPLE 7 (cis)-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid 4-hydroxy-cydohexyl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and (cis)-cydohexane-1,4-diol, the title compound was obtained as colorless crystals (40% yield). MS: m/e=408(M+H+), mp 204-206 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | EXAMPLE 10 (R)-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid tetrahydro-furan-3-yl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and (R)-tetrahydro-furan-3-ol, the title compound was obtained as white crystals (33% yield). MS: m/e=380(M+H+), mp 198-200 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With bromine; In chloroform; for 18h;Heating / reflux; | (2-Methoxy-5-morpholin-4-yl-phenyl)-thiourea (5.0 g, 19 mmol) in chloroform (130 ml) are treated with bromine (960 mul) and the mixture refluxed for 18 hours. After removal of the volatile components in vacuo, the product is recrystallized from THF (2.8 g, 57%). MS: m/e=266 (M+). |
In chloroform; bromine; | 4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine (2-Methoxy-5-morpholin-4-yl-phenyl)-thiourea (5.0 g, 19 mmol) in chloroform (130 ml) are treated with bromine (960 1) and the mixture refluxed for 18 hours. After removal of the volatile components in vacuo, the product is recrystallized from THF (2.8 g, 57%). MS: m/e=266 (M+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With pyridine; In dichloromethane; | EXAMPLE 1 (1S,4S)-2-Oxa-5-aza-bicyclo[2.2.1]heptane-5-carboxylic Acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide To a solution of <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> (265 mg, 1.0 mmol) in dichloromethane (15 ml) is subsequently added pyridine (0.24 ml, 3.0 mmol) and phenyl chloroformate (0.15 ml, 1.2 mmol) and the resulting solution stirred for 45 min at ambient temperature. Then (1S,4S)-2-oxa-5-aza-bicyclo[2.2.1]heptane (490 mg, 3.6 mmol) is added and the mixture stirred at ambient temperature for 15 min and at 40 C. for 2.5 h. After cooling to ambient temperature, saturated aqueous sodium carbonate (15 ml) is added, the organic phase is separated, dryed and the solvent evaporated in vacuo. Flash chromatography (silica, eluent: dichloromethane containing methanol (gradient from 0 to 5%)) afforded the title compound as white crystals (135 mg, 35% yield). MS: m/e=391(M+H+). Following the general method of example 1 the compounds of examples 2 to 37 were prepared as described. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.03 g (99%) | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; | a 6-Chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-nicotinamide To a stirred solution of 1.89 g (7.54 mmol) 6-chloro-nicotinic acid in 20 ml THF were added 2.87 g (7.54 mmol) HATU and 1.28 ml (7.54 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 30 minutes. A solution of 2.00 g (7.54 mmol) <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> in 20 ml dioxane and 4 ml DMF was then added and stirring continued at room temperature for 16 h. The reaction mixture was then poured into 350 ml water and the mixture stirred for 30 min. The resulting crystals were collected by filtration, washed with methanol and then with ether, and dried in vacuo to afford 3.03 g (99%) 6-chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-nicotinamide as a yellow crystalline solid. ES-MS m/e (%): 429 (M{37Cl}+Na+, 15), 427 (M{35Cl}+Na+, 38). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7.53 g (89%) | With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; | b 2-Bromo-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide To a stirred solution of 3.81 g (18.8 mmol) 2-bromo-isonicotinic acid in 50 ml THF were added 7.16 g (18.8 mmol) HATU and 3.21 ml (18.8 mmol) N-ethyldiisopropylamine and stirring continued at room temperature for 90 minutes. A solution of 5.00 g (18.8 mmol) <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> in 50 ml dioxane and 10 ml DMF was then added and stirring continued at room temperature for 16 h. The reaction mixture was then poured into 300 ml 1 M hydrochloric acid and the mixture stirred for 20 min. The resulting crystals were collected by filtration, washed with water and then with ether, and dried in vacuo to afford 7.53 g (89%) 2-bromo-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide as a yellow crystalline solid. ES-MS m/e (%): 473 (M{81Br}+Na+, 30), 471 (M{79Br}+Na+, 34). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethyl acetate; | EXAMPLE 68 (INTERMEDIATE) 2-Chloromethyl-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide To a solution of <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> (2.3 g, 8.7 mmol) in tetrahydrofurane (80 ml) is added N-ethyldiisopropylamine (6.0 ml, 35 mmol) and the solution cooled to 0 C. 2-chloromethyl-isonicotinoyl chloride (2.4 g, 10.5 mmol), dissolved in tetrahydrofurane (50 ml), is added over 15 minutes and the mixture heated to 70 C. for 1 h. After evaporation of the volatile components, the residue was dissolved in ethyl acetate and water, filtered and the resdidue combined with the dryed and evaporated organic phase. Recrystallization from dichloromethane/ethyl acetate afforded the title compound as light brown solid (2.9 g, 81% yield). MS: m/e=420(M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | EXAMPLE 72 5-Methyl-thiophene-2-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using 5-methyl-thiophene-2-carbonyl chloride and 2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol the title compound was obtained as a yellow solid in 97% yield. MS: m/e=390 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | In toluene; | EXAMPLE 136 Morpholine-4-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Conversion of <strong>[383865-57-4]2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol</strong> (100 mg, 0.377 mg) with phosgene (20% in toluene, 0.2 ml) and morpholine (0.041 ml, 0.47 mmol) using the general procedure D affords the product as white solid in 25% yield. MS: m/e=379 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In toluene; | EXAMPLE 135 Thiomorpholine-4-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Conversion of <strong>[383865-57-4]2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol</strong> (100 mg, 0.377 mg) with phosgene (20% in toluene, 0.2 ml) and thiomorpholine (0.045 ml, 0.47 mmol) using the general procedure D affords the product as white solid in 73% yield. MS: m/e=395 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In tetrahydrofuran; methanol; dichloromethane; | Tetrahydro-pyran-4-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide To a solution of <strong>[383865-57-4]2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol</strong> (100 mg, 0.4 mmol) in tetrahydrofurane (2 ml) were subsequently added N-ethyl-diisopropylamine (194 1, 1.1 mmol) and tetrahydropyran-4-carbonyl chloride (77 mg, 0.52 mmol, dissolved in 0.5 ml tetrahydrofurane) and the mixture refluxed for 3 h. The mixture was then cooled to 0 C., methanol (0.4 ml) was added and the mixture slowly warmed to 20 C. Then the mixture was evaporated to dryness, dichloromethane was added (3 ml) and extracted with saturated aqueous sodium carbonate. After back extraction of the aqueous phase with two portions of dichloromethane (3 ml), the combined organic phases were dryed with Na2SO4 and the solvent evaporated. The crude product was was then chromatographed over SiO2, eluding with CH2Cl2/MeOH 98:2, the product fractions were pooled and the solvent evaporated, to afford the title compound as a beige powder (142 mg, 76% yield), MS: m/e=378(M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; | 2-Chloro -N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-6-methyl-isonicotinamide To a stirred suspension of <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> (13.3 g, 50.1 mmol) in THF (700 ml) was added N-ethyldiisopropylamine (21.3 ml, 125 mmol). The mixture was then cooled to 5 C. and a solution of 2-chloro-6-methyl-isonicotinoyl chloride (10.5 g, 55.1 mmol) in dichloromethane (350 ml) was added dropwise over 2 hours. The reaction mixture was then stirred overnight at 20 C. To this mixture was added methanol (40 ml) and stirring continued for ten minutes. The mixture was then concentrated in vacuo and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phases were then dried over Na2SO4 and the solvent evaporated. The crude product was then chromatographed over SiO2 (Merck 230-400 mesh) eluding with CH2Cl2/MeOH (98:2), the product fractions were pooled and the solvent evaporated, to afford the title compound as a brown solid (16.0 g, 76% yield), MS: m/e =421 (M{37Cl}+H+), 419 (M{35Cl}+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | In toluene; | EXAMPLE 137 3-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-1-(6-methyl-pyridin-3-ylmethyl)-urea Conversion of <strong>[383865-57-4]2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol</strong> (100 mg, 0.377 mg) with phosgene (20% in toluene, 0.2 ml) and methyl-(6-methyl-pyridin-3-ylmethyl)-amine (0.064 ml, 0.47 mmol) using the general procedure D affords the product as white solid in 25% yield. MS: m/e=429 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With pyridine; In methanol; dichloromethane; | EXAMPLE 127 4-Cloromethyl-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-benzamide and <strong>[383865-57-4]2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol</strong> (1.0 g, 3.8 mmol), 4-(chloromethyl) benzoyl chloride (810 mg, 4.2 mmol) and pyridine (0.36 ml, 4.5 mmol) are reacted in dichloromethane (20 ml) for 18 h. The reaction is quenched with water (25 ml) and brought to pH 8.0 with sodium carbonate. The mixture is extracted with dichloromethane and the combined organic layers are dried and evapoarted to dryness. Flash chromatography (silica, eluent methylene chloride containing 2.5% methanol) affords the product as white crystalls in 54% yield. MS: m/e=418 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | 1-Benzyl-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and N-benzylmethylamine the title compound was obtained as an off-white solid (94%), MS: m/e =413 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | 4-Methoxyacetyl-piperazine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-methoxyacetyl-piperazine the title compound was obtained as beige solid (84%). MS: m/e=450 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | 3-Methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 3-methyl-piperidine the title compound was obtained as white solid (50%). MS: m/e=391 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | 4-Methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-methyl-piperidine the title compound was obtained as white solid (47%). MS: m/e=391 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | 4-Methyl-piperazine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-methyl-piperazine the title compound was obtained as beige solid (20%). MS: m/e=392 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | 1-Benzyl-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and benzylamine the title compound was obtained as an off-white solid (99%), MS: m/e=399 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | [1,4']Bipiperidinyl-1'-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and [1,4']bipiperidinyl the title compound was obtained as white solid (35%). MS: m/e=461 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | 1,4-Dioxa-8-aza-spiro[4.5]decane-8-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 1,4-dioxa-8-aza-spiro[4,5]decane the title compound was obtained as beige solid (28%). MS: m/e=435 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | 3,4-Dihydro-1H-isoquinoline-2-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 1,2,3,4-tetrahydro-isoquinoline the title compound was obtained as orange solid (63%). MS: m/e=425 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | 4-(2-Hydroxy-ethyl)-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-(2-hydroxy-ethyl)-piperidine the title compound was obtained as white solid (64%). MS: m/e=421 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
69% | 3-Hydroxymethyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and 3-hydroxymethyl-piperidine the title compound was obtained as white solid (69%). MS: m/e=436 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | 4-Hydroxymethyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and 4-hydroxymethyl-piperidine the title compound was obtained as white solid (31%). MS: m/e=407 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3-phenyl-propionamide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 3-phenylpropionyl chloride the title compound was obtained as a light yellow solid (3%), MS: m/e=398 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | 4-(2-Oxo-pyrrolidin-1-ylmethyl)-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-(2-oxo-pyrrolidin-1-ylmethyl)-piperidine the title compound was obtained as white solid (29%). MS: m/e=474 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | 1-Acetyl-piperidine-4-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol</strong> and 1 -acetyl-piperidine-4-carbonyl chloride the title compound was obtained as a white solid (22%), MS: m/e=41 9(M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | 3-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)- 1-methyl-1-phenyl-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and methyl-phenyl-amine the title compound was obtained as white solid (19%). MS: m/e=399 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | 2-Methoxy-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-acetamide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and methoxyacetyl chloride the title compound was obtained as a light yellow solid (37%), MS: m/e=338 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | 2-Chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isonicotinamide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 2-chloro-isonicotinoyl chloride the title compound was obtained as a brown solid (59%), MS: m/e 407 (M{37Cl}+H+), 405 (M{35Cl}+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | 4-Oxo-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and piperidin-4-one the title compound was obtained as white solid (38%). MS: m/e=391 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
10% | 4-Dimethylamino-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-butyramide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-dimethylamino-butyryl chloride the title compound was obtained as a light yellow solid (10%), MS: m/e=379 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | 4-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl-carbamoyl)-piperazine-1-carboxylic acid methyl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and piperazine-1-carboxylic acid methyl ester the title compound was obtained as white solid (90%). MS: m/e=436 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-2-phenyl-acetamide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and phenylacetyl chloride the title compound was obtained as a light yellow solid (37%), MS: m/e=384 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | N-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-isobutyramide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and isobutyryl chloride the title compound was obtained as a light yellow solid (8%), MS: m/e=336 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Pentanoic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and valeroyl chloride the title compound was obtained as a light yellow solid (48%), MS: m/e=350 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | 1-(2-Dimethylamino-ethyl)-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 2-dimethylamino-ethylamine the title compound was obtained as an off-white solid (79%), MS: m/e=380 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | 1-(2-Methoxy-ethyl)-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and (2-methoxy-ethyl)-methyl-amine the title compound was obtained as white solid (65%). MS: m/e=381 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | 4-Ethyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and 4-ethyl-piperidine the title compound was obtained as white solid (26%). MS: m/e=406 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | 4-Hydroxy-4-phenyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-hydroxy-4-phenyl-piperidine the title compound was obtained as light yellow solid (36%). MS: m/e=469 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | 1-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3-phenethyl-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 2-phenylethylamine the title compound was obtained as an off-white solid (87%), MS: m/e=413 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | 4-(2-Methoxy-ethyl)-piperazine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-(2-methoxy-ethyl)-piperazine-the title compound was obtained as off-white solid (79%). MS: m/e=437 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | 4-](4-Fluoro-phenylamino)-methyl]-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and 4-[(4-fluoro-phenylamino)-methyl]-piperidine the title compound was obtained as off-white solid (25%). MS: m/e=522 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | 3-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-(4-methoxy-phenyl)-1-methyl-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-methoxy-phenyl)-methyl-amine the title compound was obtained as light yellow solid (40%). MS: m/e=430 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | 4-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-ylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester Using <strong>[383865-57-4]2-amino-4-methoxy-7-morpholin-4-yl-benzothiazol</strong> and 4-chlorocarbonyl-piperidine-1-carboxylic acid tert-butyl ester the title compound was obtained as a white solid (3%), MS: m/e=477(M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | [1-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl-carbamoyl)-piperidin-4-ylmethyl]-carbamic acid methyl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and piperidin-4-ylmethyl-carbamic acid methyl ester the title compound was obtained as white solid (81%). MS: m/e=464 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | 4-Cyanomethyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-cyanomethyl-piperidine the title compound was obtained as white solid (46%). MS: m/e=416 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
27% | 4-Cyclopropyl-4-hydroxy-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-cyclopropyl-4-hydroxy-piperidine the title compound was obtained as white solid (27%). MS: m/e=434 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16% | 4-Trifluoromethyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-trifluoromethyl-piperidine the title compound was obtained as white solid (16percent) MS: m/e=445 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | 4-Hydroxy-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and piperidin-4-ol the title compound was obtained as yellow solid (50%). MS: m/e=393 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | 4-Methoxy-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and 4-methoxy-piperidine the title compound was obtained as yellow solid (33%). MS: m/e=407 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20% | (4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and ammonia the title compound was obtained as a white solid (20%), MS: m/e =309 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | (4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid phenyl ester Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and without adding an amine the title compound was obtained as a white foam (75%), MS: m/e =386 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | 3-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1-methyl-1-phenethyl-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-ylamine</strong> and N-methyl-2-phenylethylamine the title compound was obtained as an off-white solid (53%), MS: m/e 427 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | 1-(2-Dimethylamino-ethyl)-3-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)- 1-methyl-urea Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and N,N,N'-trimethylethylenediamine the title compound was obtained as an off-white solid (61%) MS: m/e=394 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | Octahydro-quinoline-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and octahydro-quinoline the title compound was obtained as white solid (79%). MS: m/e=432 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | Octahydro-isoquinoline-2-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide Using <strong>[383865-57-4]4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine</strong> and octahydro-isoquinoline the title compound was obtained as white solid (53%). MS: m/e=432 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; | (4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-carbamic acid 2-methoxy-ethyl ester 4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl-amine (300 mg, 1.1 mmol) and N-ethyldiisopropylamine (0.56 ml, 3.4 mmol) were dissolved in tetrahydrofurane (11 ml) and 2-methoxyethyl chloroformate (0.19 ml, 1.4 mmol) were added over 5 min. Then the mixture was heated to 70 C. for 3 h. The mixture was cooled to room temperature, water added and extracted twice with ethyl acetate. TRhe combined organic phases were dryed with Na2SO4 and evapprated to dryness. The title compound was obtained as off-white solid (52%). MS: m/e=368 (M+H+). |
Tags: 383865-57-4 synthesis path| 383865-57-4 SDS| 383865-57-4 COA| 383865-57-4 purity| 383865-57-4 application| 383865-57-4 NMR| 383865-57-4 COA| 383865-57-4 structure
[ 5464-79-9 ]
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Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
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P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
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P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
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P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
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P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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