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CAS No. : | 109903-35-7 | MDL No. : | MFCD00671697 |
Formula : | C8H12N2O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CIWNHTXCBHTWRV-UHFFFAOYSA-N |
M.W : | 200.26 | Pubchem ID : | 2778131 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.25 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 52.39 |
TPSA : | 80.57 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.42 cm/s |
Log Po/w (iLOGP) : | 0.63 |
Log Po/w (XLOGP3) : | 0.14 |
Log Po/w (WLOGP) : | 1.25 |
Log Po/w (MLOGP) : | 0.12 |
Log Po/w (SILICOS-IT) : | -0.04 |
Consensus Log Po/w : | 0.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.31 |
Solubility : | 9.73 mg/ml ; 0.0486 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.39 |
Solubility : | 8.19 mg/ml ; 0.0409 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.81 |
Solubility : | 0.309 mg/ml ; 0.00154 mol/l |
Class : | Soluble |
PAINS : | 1.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.08 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P261-P264-P270-P272-P280-P301+P310+P330-P302+P352-P305+P351+P338-P333+P313-P337+P313-P405-P501 | UN#: | 2811 |
Hazard Statements: | H301-H317-H320 | Packing Group: | Ⅲ |
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 |
---|---|---|
With bromine; sodium hydrogencarbonate; In methanol; dichloromethane; | EXAMPLE 48 2,6-Dibromo-<strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> To a stirred solution of <strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> (10 g) in a mixture of methylene chloride (100 mL) and methanol (200 mL) was added sodium bicarbonate (12.6 g) followed by bromine (16 g) in methylene chloride (80 mL). Then the reaction mixture was evaporated in vacuo and the residue partitioned between ethyl acetate (200 mL) and water (100 mL). The ethyl acetate phase was washed with water and brine then dried and evaporated to give the title compound as a brown solid (17.1 g). mp 155-157 C. 1 H NMR (CDCl3) delta7.4 (s, 2H), 4.6 (bs, 2H), 4.1 (m, 3H), 2.75 (d, 3H). | |
With bromine; sodium hydrogencarbonate; In methanol; dichloromethane; | EXAMPLE 48 2,6-Dibromo-<strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> To a stirred solution of <strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> (10 g) in a mixture of methylene chloride (100 mL) and methanol (200 mL) was added sodium bicarbonate (12.6 g) followed by bromine (16 g) in methylene chloride (80 mL). Then the reaction mixture was evaporated in vacuo and the residue partitioned between ethyl acetate (200 mL) and water (100 mL). The ethyl acetate phase was washed with water and brine then dried and evaporated to give the title compound as a brown solid (17.1 g). mp 155-157 C. 1 H NMR (CDCL3) delta7.4 (s, 2H), 4.6 (bs, 2H), 4.1 (m, 3H), 2.75 (d, 3H). | |
With bromine; sodium hydrogencarbonate; In methanol; dichloromethane; | EXAMPLE 48 2,6-Dibromo-<strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> To a stirred solution of <strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> (10 g) in a mixture of methylene chloride (100 mL) and methanol (200 mL) was added sodium bicarbonate (12.6 g) followed by bromine (16 g) in methylene chloride (80 mL). Then the reaction mixture was evaporated in vacuo and the residue partitioned between ethyl acetate (200 mL) and water (100 mL). The ethyl acetate phase was washed with water and brine then dried and evaporated to give the title compound as a brown solid (17.1 g). mp 155-157 C. 1 H NMR (CDCL3) delta 7.4 (s, 2H), 4.6 (bs, 2H), 4.1 (m, 3H), 2.75 (d, 3H). |
With bromine; sodium hydrogencarbonate; In methanol; dichloromethane; | EXAMPLE 48 2,6-Dibromo-<strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> To a stirred solution of <strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> (10 g) in a mixture of methylene chloride (100 mL) and methanol (200 mL) was added sodium bicarbonate (12.6 g) followed by bromine (16 g) in methylene. chloride (80 mL). Then the reaction mixture was evaporated in vacuo and the residue partitioned between ethyl acetate (200 mL) and water (100 mL). The ethyl acetate phase was washed with water and brine then dried and evaporated to give the title compound as a brown solid (17.1 g). mp 155-157 C. 1 H NMR (CDCl3) delta7.4 (s, 2H), 4.6 (bs, 2H), 4.1 (m, 3H), 2.75 (d, 3H). | |
With bromine; sodium hydrogencarbonate; In methanol; dichloromethane; | EXAMPLE 48 2,6-Dibromo-<strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> To a stirred solution of <strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> (10 g) in a mixture of methylene chloride (100 mL) and methanol (200 mL) was added sodium bicarbonate (12.6 g) followed by bromine (16 g) in methylene chloride (80 mL). Then the reaction mixture was evaporated in vacuo and the residue partitioned between ethyl acetate (200 mL) and water (100 mL). The ethyl acetate phase was washed with water and brine then dried and evaporated to give the title compound as a brown solid (17.1 g). mp 155-157 C. 1 H NMR (CDCL3) delta7.4 (s, 2H), 4.6 (bs, 2H), 4.1 (m, 3H), 2.75 (d, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
C-(4-hydrazino-phenyl)-n-methyl-methanesulfonamide hydrochloride: A solution of sodium nitrite (7.6 g, 110 mmol) in water was added dropwise to a suspension of C-(4-aminophenyl)-N-methyl-methanesulfonamide (20 g, 100 mmol) in concentrated hydrochloric acid (106 mL) at -10 C. The resulting mixture was stirred at -5 C. for 30 minutes and filtered into a pre-cooled flask. The solution was added dropwise to a cooled and stirred solution of tin chloride dihydrate (90.3 g, 400 mmol) in concentrated hydrochloric acid (106 mL) at -5 C. The resulting suspension was warmed to ambient temperature, filtered and the solid product was washed with ether and hexane, dried under vacuum to give the title compound. 1H-NMR (300 MHz, DMSO-d6) delta 10.30 (s, 3H), 7.24 (d, J=8.4 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 4.22 (s, 2H), 2.50 (s, 3H). LC-MS (m/z): 216 (M+1)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In ethanol; at 60℃; for 27h; | A suspension of [1- [4- (2-CHLORO-PYRIMIDIN-4-YLOXY)-PHENYL]-3- (4-PIPERIDIN-1-YL-3-TRIFLUOROMETHYL-] phenyl)-urea (compound of Example 79; 140 mol, 0.285 [MMOL)] and of C- (4-amino-phenyl)- [N-METHYL-METHANESULFONAMIDE] (855 mg, 4.27 [MMOL)] in ethanol (5 mL) is stirred in a sealed tube at [60 C] for 27 h. After evaporating the solvent, the reaction mixture is flash chromatographed (silica gel, 2.5 x 45 cm, hexane/AcOEt = 1 [: 1 O 1] : 2) to give compound of Example 138 as a beige solid : M+H = 655.8 ; Rf (Hexane/AcOEt = 1 : 1): 0.319 ; HPLC: 6.65 min (System 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; for 24 - 72h; | To a solution of indazole-3-carboxylic acid (Fluka) (405 mg, 2.5 mmol, 1.0 equiv) in dichloromethane (10 [ML)] was added an amine or appropriately substituted aniline (3.0 mmol, 1.2 equiv), [N, N DIISOPROPYLETHYLAMINE] (1.6 ml, 9.0 mmol, 3.6 equiv) [AND 0-(7-AZABENZOTRIAZOL-1-YL)-N, N, N', N'-TETRAMETHYLURONIUM] hexafluorophosphate (1.05 g, 2.75 mmol, 1.1 equiv). The mixture was stirred for a period of 24-72 hours and additional [0-(7-AZABENZOTRIAZOL-1-YL)-N, N, N', N'-] [TETRAMETHYLURONIUM] hexafluorophosphate was added if necessary. The reaction was quenched with water (10 [ML)] and dichloromethane (10 ml). The compounds were purified as described in the examples below, and characterised by liquid chromatography and mass spectrometry using either of the systems described above. Procedure A was followed. Water and dichloromethane were removed by filtration and the solid was triturated with water and dichloromethane. The title compound was dried in vacuo to afford 119 mg [(14%) ;] LCMS 2.92 min, mlz [M+H] [+] 345. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20 - 70℃; for 50h; | To the [NITRO-LH-INDAZOLE-3-CARBOXYLIC] acid (1 equiv. ) of Example 63A in DMF (0.3 M) was added EDC (1.2 equiv. ), HOBT (1.2 equiv. ), NMM (1.2 equiv. ) and then 4- [METHYLSULPHAMOYLMETHYL-PHENYLAMINE] (1.3 equiv. ) at room temperature. The reaction was heated to [70 C] for 2 hours and then stirred at room temperature for 48 hours. Water was added to the reaction mixture and the precipitated product was filtered. The solid was washed with water, then a small volume [OF MEOH,] and then dried in a vacuum oven to leave a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In i-Amyl alcohol; | N-Methyl-[4-(4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride A solution of 2-chloro-4-phenylamino-quinazoline (0.92 g) (prepared as described in Example 1a and N-methyl-(4-aminophenyl)-methanesulfonamide (0.80 g) in 10 ml of isopentylalcohol is stirred under nitrogen at 170 C. for 15 min in a sealed vessel. The warm reaction mixture is diluted with 10 ml ethanol and the hydrochloride salt, which is crystallizing on cooling, is filtered off to yield N-methyl-[4-(4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride as light yellow crystals melting at 259-263 C.; Rf (A2) 0.11, FAB-MS: (M+H)+ =420. Analytical data: C22 H21 N5 O2 S+HCl. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In i-Amyl alcohol; ethyl acetate; | N-Methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride A solution of 2-chloro-6-methoxy-4-phenylamino-quinazoline (1.15 g) and N-methyl-(4-aminophenyl)-methanesulfonamide (prepared as described in Tetrahedron Letters 1992, 33, 8011) (0.89 g) in 5 ml of isopentylalcohol is stirred under nitrogen at 180 C. for 20 min in a sealed vessel. The warm reaction mixture is diluted with methanol and the hydrochloride salt, which is crystallizing on cooling, is filtered off. The crude product is redissolved in ethylacetate and aqueous sodium carbonate solution and extracted with ethylacetate. The organic extracts are dried and evaporated and the solid residue is titurated with diethylether to give N-methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide as light yellow crystals melting at 212-215 C.; (Rf (A2) 0.16. Recrystallisation from methanolic hydrogen chloride and diethylether yields N-methyl-[4-(6-methoxy-4-phenylamino-quinazolin-2-ylamino)-phenyl]-methanesulfonamide hydrochloride as light yellow crystals melting at 264-268 C.; Rf (A2) 0.16, FAB-MS: (M+H)+ =450. Analytical data: C23 H23 N5 O3 S+HCl. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.13 g (65%) | With Iodine monochloride; In hexane; ethyl acetate; acetonitrile; | 4-Amino-3-iodo-N-methylbenzenemethanesulfonamide To a suspension of 1.06 g (5.31 mmol, 1.0 equiv.) of <strong>[109903-35-7]4-amino-N-methylbenzenemethanesulfonamide</strong> in 20 mL of acetonitrile was added 0.862 g (5.31 mmol, 1.0 equiv.) of iodine monochloride. The reaction was stirred for 15 minutes at room temperature. The mixture was partitioned between 25 mL of ethyl acetate and 15 mL of 20% aqueous sodium thiosulfate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield an oil. The oil was filtered through a plug of silica gel using 40% ethyl acetate in hexane to yield 1.13 g (65%) of 4-amino-3-iodo-N-methylbenzenemethanesulfonamide |
1.13 g (65%) | With Iodine monochloride; In hexane; ethyl acetate; acetonitrile; | 4-Amino-3-iodo-N-methylbenzenemethanesulfonamide To a suspension of 1.06 g (5.31 mmol, 1.0 equiv.) of <strong>[109903-35-7]4-amino-N-methylbenzenemethanesulfonamide</strong> in 20 mL of acetonitrile was added 0.862 g (5.31 mmol, 1.0 equiv.) of iodine monochloride. The reaction was stirred for 15 minutes at room temperature. The mixture was partitioned between 25 mL of ethyl acetate and 15 mL of 20% aqueous sodium thiosulfate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield an oil. The oil was filtered through a plug of silica gel using 40% ethyl acetate in hexane to yield 1.13 g (65%) of 4-amino-3-iodo-N-methylbenzenemethanesulfonamide |
1.13 g (65%) | With Iodine monochloride; In hexane; ethyl acetate; acetonitrile; | 4-Amino-3-iodo-N-methylbenzenemethanesulfonamide To a suspension of 1.06 g (5.31 mmol, 1.0 equiv.) of <strong>[109903-35-7]4-amino-N-methylbenzenemethanesulfonamide</strong> in 20 mL of acetonitrile was added 0.862 g (5.31 mmol, 1.0 equiv.) of iodine monochloride. The reaction was stirred for 15 minutes at room temperature. The mixture was partitioned between 25 mL of ethyl acetate and 15 mL of 20% aqueous sodium thiosulfate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield an oil. The oil was filtered through a plug of silica gel using 40% ethyl acetate in hexane to yield 1.13 g (65%) of 4-amino-3-iodo-N-methylbenzenemethanesulfonamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; trifluoroacetic anhydride; In dichloromethane; | EXAMPLE 46 4-Methylaminosulfonylmethyl-N-trifluoroacetylaniline To a chilled solution of pyridine (4 mL) in methylene chloride (100 mL) was added trifluoroacetic anhydride (7.0 m L) follow e d by <strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> (9.55 g). After 30 minutes at 0 C., the reaction mixture was filtered to give the title compound (11.6 g) as a light yellow powder. TLC (EtOAc/hexane 2:1) Rf=0.36. | |
With pyridine; trifluoroacetic anhydride; In dichloromethane; | EXAMPLE 46 4-Methylaminosulfonylmethyl-N-trifluoroacetylaniline To a chilled solution of pyridine (4 mL) in methylene chloride (100 mL) was added trifluoroacetic anhydride (7.0 mL) followed by <strong>[109903-35-7]4-methylaminosulfonylmethylaniline</strong> (9.55 g). After 30 minutes at 0 C., the reaction mixture was filtered to give the title compound (11.6 g) as a light yellow powder. TLC (EtOAc/hexane 2:1) Rf=0.36. | |
With pyridine; trifluoroacetic anhydride; In dichloromethane; | EXAMPLE 46 4-Methylaminosulfonylmethyl-N-trifluoroacetylaniline To a chilled solution of pyridine (4 mL) in methylene chloride (100 mL) was added trifluoroacetic anhydride (7.0 mL) followed by 4methylaminosulfonylmethylaniline (9.55 g). After 30 minutes at 0 C., the reaction mixture was filtered to give the title compound (11.6 g) as a light yellow powder. TLC (EtOAc/hexane 2:1) Rf=0.36. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide; at 80℃; for 2h; | Example 2; Synthesis of C-{4-[4-(2-Methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-N-methyl-methanesulfonamide (Compound 2); A solution of 2-chloro-4-(2-methoxy-phenyl)-pyrimidine (0.883 g, 0.004 mol), and <strong>[109903-35-7]C-(4-amino-phenyl)-N-methyl-methanesulfonamide</strong> (0.801 g, 0.004 mol) (Macor, John E.; Blank et al., Tetrahedron Letters (1992), 33(52), 8011-14) in DMF is stirred in DMF (12 ml) for 2 hours at 80 C. (TLC control). The solvent was removed under reduced pressure to give C-{4-[4-(2-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-N-methyl-methanesulfonamide. | |
In N,N-dimethyl-formamide; at 80℃; for 2h; | Example 2: Synthesis of C-{4-[4-(2-Methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-N- methyl-methanesulfonamide (Compound 2); A solution of 2-chloro-4-(2-methoxy-phenyl)-pyrimidine (0.883 g, 0.004 mol), and C-(4- amino-phenyl)-N-methyl-methanesulfonamide (0.801 g, 0.004 mol) (Macor, John E.; Blank et al., Tetrahedron Letters (1992), 33(52), 801 1 -14) in DMF is stirred in DMF (12 ml) for 2 hours at 80C (TLC control). The solvent was removed under reduced pressure to give C-{4-[4-(2-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl}-N-methyl- methanesulfonamide. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 23: 1-(4-[5-acetyl-3-ethyl-4-methyl-1,3-thiazol-2(3H)- ylidene]amino}phenyl)-lambda/-methylmethanesulfonamide hydrochloride; A mixture of 4-amino-N-methyl-alpha-toluenesulphonamide (200mg, I .Ommol), ethyl isothiocycanate (104mg, 1.20mmol, 0.1 ml) and triethylamine (0.2ml) in ethanol (5ml) was stirred at reflux for 2 hours. The solvent was then removed by rotary evaporation, the resulting material was then suspended in toluene (5ml) and treated with 3-chloro-2,4- pentanedione (0.14g, 1.05mmol, 0.13ml) and the whole mix stirred at 9O0C (oil bath temperature) for 3 hours, and allowed to cool. The reaction mix was filtered and the filtrate evaporated under reduced pressure to give a yellow oil, which was purified by MDAP (mass directed auto-preparation). The relevant fractions were combined and the solvent removed by rotary evaporation to give a brown oil, which was dissolved in dichloromethane (1 ml) and treated with 1 M ethereal HCI (1 ml). The solvent was removed by air drying. The product was triturated in ether, the liquid was decanted off and the residual material was vacuum oven dried to give the title compound as a beige coloured solid (98mg, 24%).LC/MS (ES): Found 368 (ES+), retention time 2.35mins. Ci6H2IN3O3S2 requires 367. 1 H-NMR (400MHz, MeOD-d4): delta 1.49 (3H, t, J=7Hz), 2.52 (3H, s), 2.71 (3H, s), 2.76 (3H, s), 4.31 (2H, m), 4.42 (2H, s), 7.55 (2H, m), 7.66 (2H, d, J=8Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate A24: 1 -(4-(5-Amino-3-ferf-butyl-1 H-pyrazol-1 -yl)phenyl)-/V-methyl methanesulfonamide.Intermediate A24To a suspension of 1-(4-aminophenyl)-A/-methylmethanesulfonamide (500 mg, 2.50 mmol) in hydrochloric acid (6 M, 10 mL) at 0C was added a soution of sodium nitrite (181 mg, 2.62 mmol) in water (3.0 mL) over 5 min. The reaction mixture was maintained at 0C for 2.5 hr, was treated with tin(ll) chloride (1.33 g, 6.99 mmol) in hydrochloric acid (6M, 15 mL) and was then warmed to RT for 64 hr. The resulting mixture was basified to pH 12 with aq NaOH (6.0 M) and was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with water and then dried and evaporated in vacuo to give a residue that was suspended in ethanol (10 mL) and treated with 4,4-dimethyl-3-oxopentanenitrile (160 mg, 1.3 mmol) and cone hydrochloric acid (12 M, 106 mu, 1.27 mmol). The resulting mixture was heated at reflux for 5 hr and after a further 23 hr at RT was evaporated in vacuo, to remove the ethanol and the resulting aq mixture basified with aq NaOH (2.0 M) and then extracted with DCM (2 x 30 mL). The combined organic extracts were dried and evaporated in vacuo to afford the title compound, Intermediate A24, as an orange solid (146 mg, 85% purity, 15%); R1 1 .34 min (Method 2); m/z 323 (M+H)+, (ES+). This material was used in subsequent steps without further purification | ||
Intermediate A13: 1 -(4-(5-Amino-3-ieri-butyl-1 H-pyrazol-1 -yl)phenyl)-yV-methyl methanesulfonamide.; Intermediate A13; To a suspension of 1 -(4-aminophenyl)-/V-methylmethanesulfonamide (500 mg, 2.50 mmol) in hydrochloric acid (6 M, 10 mL) at 0C was added a soution of sodium nitrite (181 mg, 2.62 mmol) in water (3.0 mL) over 5 min. The reaction mixture was maintained at 0C for 2.5 hr, was treated with tin(ll) chloride (1.33 g, 6.99 mmol) in hydrochloric acid (6M, 15 mL) and was then warmed to RT for 64 hr. The resulting mixture was basified to pH 12 with aq NaOH (6.0 M) and was extracted with EtOAc (2 x 100 mL). The combined organic extracts were washed with water and then dried and evaporated in vacuo to give a residue that was suspended in ethanol (10 mL) and treated with 4,4-dimethyl-3-oxopentanenitrile (160 mg, 1 .3 mmol) and cone hydrochloric acid (12 M, 106 mu, 1 .27 mmol). The resulting mixture was heated at reflux for 5 hr and after a further 23 hr at RT was evaporated in vacuo, to remove the ethanol. The resulting aq mixture was basified with aq NaOH (2.0 M) and was then extracted with DCM (2 x 30 mL). The combined organic extracts were dried and evaporated in vacuo to afford the title compound, Intermediate A13, as an orange solid (146 mg, 85% purity, 15%); R' 1.34 min (Method 2); m/z 323 (M+H)+, (ES+). This material was used in subsequent steps without further purification. | ||
Intermediate A13: 1-(4-(5-Amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl)-N-methyl methanesulfonamide To a suspension of <strong>[109903-35-7]1-(4-aminophenyl)-N-methylmethanesulfonamide</strong> (500 mg, 2.50 mmol) in hydrochloric acid (6 M, 10 mL) at 0 C. was added a solution of sodium nitrite (181 mg, 2.62 mmol) in water (3.0 mL) over 5 min. The reaction mixture was maintained at 0 C. for 2.5 hr, was treated with tin(II) chloride (1.33 g, 6.99 mmol) in hydrochloric acid (6M, 15 mL) and was then warmed to RT for 64 hr. The resulting mixture was basified to pH 12 with aq NaOH (6.0 M) and was extracted with EtOAc (2*100 mL). The combined organic extracts were washed with water and then dried and evaporated in vacuo to give a residue that was suspended in ethanol (10 mL) and treated with 4,4-dimethyl-3-oxopentanenitrile (160 mg, 1.3 mmol) and conc hydrochloric acid (12 M, 106 muL, 1.27 mmol). The resulting mixture was heated at reflux for 5 hr and after a further 23 hr at RT was evaporated in vacuo, to remove the ethanol. The resulting aq mixture was basified with aq NaOH (2.0 M) and was then extracted with DCM (2*30 mL). The combined organic extracts were dried and evaporated in vacuo to afford the title compound, Intermediate A13, as an orange solid (146 mg, 85% purity, 15%); Rt 1.34 min (Method 2); m/z 323 (M+H)+, (ES+). This material was used in subsequent steps without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With sulfuric acid; sodium nitrite; In water; at 0 - 100℃; | Preparation 1 1-(4-Hydroxyphenyl)-N-methyl-methanesulfonamide Add sulfuric acid (2.5 mL, 44.9 mmol) to a suspension of <strong>[109903-35-7]1-(4-aminophenyl)-N-methyl-methanesulfonamide</strong> (7.5 g, 37.5 mmol) in water (56.2 mL) and chill the reaction mixture to 0 C. Slowly, drop wise add a solution of sodium nitrite (2.8 g; 41.2 mmol) in water (37.5 mL) to this slurry. Stir the resulting mixture at 0 C. for 20 m, then remove the ice bath and heat the reaction at 100 C. Cool the mixture to room temperature. Quench the reaction with an excess of water and extract with EtOAc. Combine the EtOAc extracts, wash the extracts with brine; dry over MgSO4; filter; and concentrate the filtrate under reduced pressure to yield the title compound as an orange solid (6.2 g, 66%). MS (m/z): 219 (M+H2O). |
Tags: 109903-35-7 synthesis path| 109903-35-7 SDS| 109903-35-7 COA| 109903-35-7 purity| 109903-35-7 application| 109903-35-7 NMR| 109903-35-7 COA| 109903-35-7 structure
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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. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
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. |
P284 | Wear respiratory protection. |
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: |
P309 | IF exposed or if you feel unwell: |
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. |
P361 | Remove/Take off immediately all contaminated clothing. |
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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