[ CAS No. 1208319-27-0 ] {[proInfo.proName]}

Name: 1208319-27-0|N-methyl-1-(trans-4-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)cyclohexyl)methanesulfonamide maleate(1:x)|98%
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Quality Control of [ 1208319-27-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1208319-27-0 ]

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 :

Safety of [ 1208319-27-0 ]

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:

Application In Synthesis of [ 1208319-27-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 1208319-27-0 ]

[ 1208319-27-0 ] Synthesis Path-Downstream 1~15

1
[ 2124221-11-8 ]
[ 1208319-27-0 ]

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

Reference： [1]Current Patent Assignee: ZOETIS INC. - US2017/233397, 2017, A1

2
[ 2124221-12-9 ]
[ 1208319-27-0 ]

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

Reference： [1]Current Patent Assignee: ZOETIS INC. - US2017/233397, 2017, A1

3
[ 1208319-26-9 ]
[ 110-16-7 ]
[ 1208319-27-0 ]

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).

Reference： [1]Current Patent Assignee: LIANYUNGANG YAHUI PHARMACHEM; CHANGZHOU YABANG QH PHARMACHEM; INNER MONGOLIA QIHUI PHARMACEUTICAL - CN112279854, 2021, A Location in patent: Paragraph 0064-0066; 0083-0085
[2]Current Patent Assignee: ZOETIS INC. - US2017/233397, 2017, A1 Location in patent: Paragraph 0135
[3]Current Patent Assignee: ZHEJIANG JIUZHOU PHARMACEUTICAL CO., LTD. - CN107365312, 2017, A Location in patent: Paragraph 0102; 0103

4
[ 589-15-1 ]
[ 1208319-27-0 ]

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

Reference： [1]Current Patent Assignee: ZOETIS INC. - US2017/233397, 2017, A1

5
[ CAS Unavailable ]
[ 1208319-27-0 ]

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

Reference： [1]Current Patent Assignee: ZOETIS INC. - US2017/233397, 2017, A1

6
[ 4746-97-8 ]
[ 1208319-27-0 ]

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

Reference： [1]Current Patent Assignee: ZHEJIANG JIUZHOU PHARMACEUTICAL CO., LTD. - CN107365312, 2017, A
[2]Current Patent Assignee: ZHEJIANG JIUZHOU PHARMACEUTICAL CO., LTD. - CN107365312, 2017, A

7
[ 2160581-82-6 ]
[ 1208319-27-0 ]

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

8
[ 2160581-83-7 ]
[ 1208319-27-0 ]

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