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CAS No. : | 1208319-27-0 | MDL No. : | MFCD30533388 |
Formula : | C19H27N5O6S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VQIGDTLRBSNOBV-BTJKTKAUSA-N |
M.W : | 453.51 | Pubchem ID : | 44631937 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
Multi-step reaction with 4 steps 1.1: hydrogen; 10% palladium charcoal / water; methanol / 16 h / 70 °C / 1551.49 Torr 2.1: potassium carbonate / water; acetonitrile / 4 h / 75 °C 3.1: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 3 h / 35 °C 3.2: 15 °C 4.1: water / 37 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: potassium carbonate / water; acetonitrile / 4 h / 75 °C 2.1: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 3 h / 35 °C 2.2: 15 °C 3.1: water / 37 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.6% | With pyrographite In ethanol at 78 - 80℃; | 5; 10 Preparation of trans-N-methyl-4-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)cyclohexylmethanesulfonamide maleate Add 150ml of 95 ethanol and 24.0g of trans-N-methyl-4-(methyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)cyclohexylmethanesulfonamide to a 500ml reaction flask. 0.071mol) and 8.2g (0.071mol) of maleic acid, 1.0g of activated carbon, heat up to 78-80°C, keep the temperature for 1-2 hours, filter with suction, cool the filtrate to 5-10°C, stir for 1-2 hours, pump Filter, rinse the filter cake with 95% ethanol, and dry the filter cake in vacuum at 50-60°C to obtain white trans-N-methyl-4-(methyl-7H-pyrrolo[2,3-d] Pyrimidine-4-ylamino)cyclohexylmethanesulfonamide maleate 30.6g, the yield was 95.6%. |
In water at 37 - 60℃; | 1 Formula 1 Compound Salt Formation, Example 1 To a flask was charged maleic acid (9.5 g, 81.8 mmol), N-methyl-1-{trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}methanesulfonamide (Formula 1 compound; 25 g, 74.1 mmol), and water (250 mL). This was heated to about 60° C. and the materials formed a clear solution. The solution was cooled to about 55° C. and seeded with previously isolated maleic acid salt of the Formula 1 compound (25 mg, 0.7 mmol). The reaction was cooled to about 37° C. at a rate of about 1° C. per hour and then to about 5° C. at a rate of about 3° C. per hour. The product was isolated by filtration and washed with water (100 mL). This afforded 30.9 g of white material, N-methyl-1-{trans-4-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}methanesulfonamide, maleate, as the monohydrate, Form B(A). 1H NMR (600 MHz, DMSO-d6) 12.0 (s, 1H), 8.18 (s, 1H), 7.25 (br s, 1H), 6.90 (q, 1H), 6.64 (br s, 1H), 6.19 (s, 2H), 4.55 (br s, 1H), 3.20 (s, 3H), 2.95 (d, 2H), 2.58 (d, 3H), 2.05 (d, 2H), 1.85 (m, 1H), 1.72 (br s, 4H), 1.30 (m, 2H). | |
253.0 g | In water; butan-1-ol at 20℃; for 18h; | 8 Example 8: Preparation of Oclacitinib maleate A mixture of the compound of Example 7 of Oclacitinib (212.0 g, 628.3 mmol) and maleic acid (67.2 g, 579.0 mmol) in 1-butanol (3200 ml) and water (400 ml) was stirred at room temperature for 18 hours.The volume of the mixture was reduced to 1600 ml by vacuum distillation (55 °C, 100 mbar) and then cooled to 0 °C.The resulting solid was collected by filtration, washed with hexane (500 ml) and dried in vacuo at 35 °C to give Oclacitinib maleate (253.0 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: sodium sulfite / water; acetonitrile / 4 h / 80 °C 2.1: copper(I) bromide / water / 16 h / 90 °C 3.1: hydrogen; 10% palladium charcoal / water; methanol / 16 h / 70 °C / 1551.49 Torr 4.1: potassium carbonate / water; acetonitrile / 4 h / 75 °C 5.1: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 3 h / 35 °C 5.2: 15 °C 6.1: water / 37 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: copper(I) bromide / water / 16 h / 90 °C 2.1: hydrogen; 10% palladium charcoal / water; methanol / 16 h / 70 °C / 1551.49 Torr 3.1: potassium carbonate / water; acetonitrile / 4 h / 75 °C 4.1: thionyl chloride; N,N-dimethyl-formamide / tetrahydrofuran / 3 h / 35 °C 4.2: 15 °C 5.1: water / 37 - 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 8 steps 1.1: n-butyllithium / tetrahydrofuran / 0.17 h / -30 °C / Inert atmosphere 1.2: 1 h / -30 °C / Inert atmosphere 2.1: pyridine; thionyl chloride / 12 h / 0 °C 3.1: triphenylphosphine hydrochloride; 1,1'-bis-(diphenylphosphino)ferrocene; hydrogen / toluene / Autoclave 4.1: hydrogenchloride / tetrahydrofuran; water / 1 h 5.1: methanol / 1.5 h / 0 °C 5.2: 5 h / -30 °C 6.1: potassium carbonate / water; 1,4-dioxane / 24 h / Reflux 7.1: sulfuric acid / 3.67 h / 0 °C 8.1: water; butan-1-ol / 18 h / 20 °C | ||
Multi-step reaction with 8 steps 1.1: n-butyllithium / tetrahydrofuran / 0.17 h / -30 °C / Inert atmosphere 1.2: 1 h / -30 °C / Inert atmosphere 2.1: pyridine; thionyl chloride / 12 h / 0 °C 3.1: triphenylphosphine hydrochloride; 1,1'-bis-(diphenylphosphino)ferrocene; hydrogen / toluene / Autoclave 4.1: hydrogenchloride / tetrahydrofuran; water / 1 h 5.1: methanol / 1.5 h / 0 °C 5.2: 5 h / -30 °C 6.1: potassium carbonate / water; 1,4-dioxane / 24 h / Reflux 7.1: sulfuric acid / 3.67 h / 0 °C 8.1: water; butan-1-ol / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1.1: pyridine; thionyl chloride / 12 h / 0 °C 2.1: triphenylphosphine hydrochloride; 1,1'-bis-(diphenylphosphino)ferrocene; hydrogen / toluene / Autoclave 3.1: hydrogenchloride / tetrahydrofuran; water / 1 h 4.1: methanol / 1.5 h / 0 °C 4.2: 5 h / -30 °C 5.1: potassium carbonate / water; 1,4-dioxane / 24 h / Reflux 6.1: sulfuric acid / 3.67 h / 0 °C 7.1: water; butan-1-ol / 18 h / 20 °C | ||
Multi-step reaction with 7 steps 1.1: pyridine; thionyl chloride / 12 h / 0 °C 2.1: triphenylphosphine hydrochloride; 1,1'-bis-(diphenylphosphino)ferrocene; hydrogen / toluene / Autoclave 3.1: hydrogenchloride / tetrahydrofuran; water / 1 h 4.1: methanol / 1.5 h / 0 °C 4.2: 5 h / -30 °C 5.1: potassium carbonate / water; 1,4-dioxane / 24 h / Reflux 6.1: sulfuric acid / 3.67 h / 0 °C 7.1: water; butan-1-ol / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: triphenylphosphine hydrochloride; 1,1'-bis-(diphenylphosphino)ferrocene; hydrogen / toluene / Autoclave 2.1: hydrogenchloride / tetrahydrofuran; water / 1 h 3.1: methanol / 1.5 h / 0 °C 3.2: 5 h / -30 °C 4.1: potassium carbonate / water; 1,4-dioxane / 24 h / Reflux 5.1: sulfuric acid / 3.67 h / 0 °C 6.1: water; butan-1-ol / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: triphenylphosphine hydrochloride; 1,1'-bis-(diphenylphosphino)ferrocene; hydrogen / toluene / Autoclave 2.1: hydrogenchloride / tetrahydrofuran; water / 1 h 3.1: methanol / 1.5 h / 0 °C 3.2: 5 h / -30 °C 4.1: potassium carbonate / water; 1,4-dioxane / 24 h / Reflux 5.1: sulfuric acid / 3.67 h / 0 °C 6.1: water; butan-1-ol / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: hydrogenchloride / tetrahydrofuran; water / 1 h 2.1: methanol / 1.5 h / 0 °C 2.2: 5 h / -30 °C 3.1: potassium carbonate / water; 1,4-dioxane / 24 h / Reflux 4.1: sulfuric acid / 3.67 h / 0 °C 5.1: water; butan-1-ol / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: methanol / 1.5 h / 0 °C 1.2: 5 h / -30 °C 2.1: potassium carbonate / water; 1,4-dioxane / 24 h / Reflux 3.1: sulfuric acid / 3.67 h / 0 °C 4.1: water; butan-1-ol / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / water; 1,4-dioxane / 24 h / Reflux 2: sulfuric acid / 3.67 h / 0 °C 3: water; butan-1-ol / 18 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 4 h / 105 °C 1.2: 7 h / -10 - -5 °C 1.3: 16 h / 20 - 25 °C 2.1: sodium sulfite / ethanol; water / 24 h / 75 - 85 °C 3.1: pyridine; oxalyl dichloride / acetonitrile / 3 h / 5 - 10 °C 3.2: 0 - 10 °C 4.1: hydrogenchloride / water / 10 h / 95 - 98 °C 4.2: 30 h / 65 °C 5.1: pyrographite / ethanol / 78 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: pyridine; oxalyl dichloride / acetonitrile / 3 h / 5 - 10 °C 1.2: 0 - 10 °C 2.1: hydrogenchloride / water / 10 h / 95 - 98 °C 2.2: 30 h / 65 °C 3.1: pyrographite / ethanol / 78 - 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium sulfite / ethanol; water / 24 h / 75 - 85 °C 2.1: pyridine; oxalyl dichloride / acetonitrile / 3 h / 5 - 10 °C 2.2: 0 - 10 °C 3.1: hydrogenchloride / water / 10 h / 95 - 98 °C 3.2: 30 h / 65 °C 4.1: pyrographite / ethanol / 78 - 80 °C |