[ CAS No. 1450833-55-2 ] {[proInfo.proName]}

Name: 1450833-55-2|((1R,2R,3S,4R)-2,3-Dihydroxy-4-((2-(3-((trifluoromethyl)thio)phenyl)pyrazolo[1,5-a]pyrimidin-7-yl)amino)cyclopentyl)methyl sulfamate|98%
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Quality Control of [ 1450833-55-2 ]

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SDS Specification

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Product Details of [ 1450833-55-2 ]

CAS No. :	1450833-55-2	MDL No. :	MFCD28964160
Formula :	C₁₉H₂₀F₃N₅O₅S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KJDAGXLMHXUAGV-DGWLBADLSA-N
M.W :	519.52	Pubchem ID :	71715374
Synonyms :	MLN7243	Chemical Name :	((1R,2R,3S,4R)-2,3-Dihydroxy-4-((2-(3-((trifluoromethyl)thio)phenyl)pyrazolo[1,5-a]pyrimidin-7-yl)amino)cyclopentyl)methyl sulfamate

Safety of [ 1450833-55-2 ]

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:

Application In Synthesis of [ 1450833-55-2 ]

* 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 [ 1450833-55-2 ]

[ 1450833-55-2 ] Synthesis Path-Downstream 1~5

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water In methanol; N,N-dimethyl-formamide for 1h;	7 Step 2: (s.e.)-((1R,2R,3S,4R)-2,3-dihydroxy-4-{([2-(1-naphthyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino}cyclopentyl)methyl sulfamate (I-98) General procedure: Step 2: (s.e.)-((1R,2R,3S,4R)-2,3-dihydroxy-4-{([2-(1-naphthyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino}cyclopentyl)methyl sulfamate (I-98) To a vial charged with (s.e.)-((3aR,4R,6R,6aS)-2,2-dimethyl-6-[2-(1-naphthyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino}tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methanol (1.76 g, 4.09 mmol) in N,N-dimethylformamide (7.20 mL) is added chlorosulfonamide (1.42 g, 12.3 mmol; obtained by the method described in J. Am. Chem. Soc. 2005, 127, 15391). After 1 hr, the reaction is quenched with methanol (5 mL). 6.0 M hydrochloric acid in water (3.41 mL, 20.4 mmol) is added and the mixture is stirred for 1 hr. Solvent is removed in vacuo and the crude material is purified by preparative HPLC to provide (s.e.)-((1R,2R,3S,4R)-2,3-dihydroxy-4-[2-(1-naphthyl)pyrazolo[1,5-a]pyrimidin-7-yl]amino}cyclopentyl)methyl sulfamate. LCMS: (AA) M+1 470; 1H NMR (400 MHz, MeOD) δ 8.48-8.40 (m, 1H), 8.19 (d, J=5.5 Hz, 1H), 7.99-7.90 (m, 2H), 7.81-7.75 (m, 1H), 7.60-7.47 (m, 3H), 6.69 (s, 1H), 6.37 (d, J=5.6 Hz, 1H), 4.24-4.06 (m, 3H), 4.04-3.99 (m, 1H), 3.96-3.89 (m, 1H), 2.55-2.45 (m, 1H), 2.45-2.35 (m, 1H), 1.60-1.48 (m, 1H).

2
[ 1450833-55-2 ]
[ 1450834-90-8 ]
[ 1450834-91-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-chloro-succinimide In N,N-dimethyl-formamide at 0 - 20℃;	17 Example 17 Synthesis of (s.e.)-{(1R,2R,3S,4R)-4-[(3,6-dichloro-2-{3-[(trifluoromethyl)sulfanyl]phenyl}pyrazolo[1,5-a]pyrimidin-7-yl)amino]-2,3-dihydroxycyclopentyl}methyl sulfamate (I-124) and (s.e.)-{(1R,2R,3S,4R)-4-[(6-chloro-2-{3-[(trifluoromethyl)sulfanyl]phenyl}pyrazolo[1,5-a]pyrimidin-7-yl)amino]-2,3-dihydroxycyclopentyl}methyl sulfamate (I-125) To a vial containing (s.e.)-{(1R,2R,3S,4R)-2,3-dihydroxy-4-[(2-{3-[(trifluoromethyl)sulfanyl]phenyl}pyrazolo[1,5-a]pyrimidin-7-yl)amino]cyclopentyl}methyl sulfamate (0.82 g, 0.0015 mol) and cooled to 0° C. is added N-chlorosuccinimide (126 mg, 0.000943 mol) as a solution in 12 mL of N,N-dimethylformamide. The reaction mixture is stirred overnight with warming to rt. Saturated sodium bicarbonate solution is added and the reaction mixture is extracted with ethyl acetate, washed with brine, dried over sodium sulfate and concentrated in vacuo. The crude material is first purified by column chromatography (eluent: methanol/methylene chloride) and then purified by HPLC to afford both the dichloro (LCMS: (FA) M+1 588) and mono chloro (LCMS: (FA) M+1 554) title compounds.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2013/217682, 2013, A1 Location in patent: Paragraph 0425; 0426

3
tert-butyl [({(3aR,4R,6aS)-2,2-dimethyl-6-[(2-{3-(trifluoromethylthio)phenyl}pyrazolo[1,5-a]pyrimidin-7-yl)amino]tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}methoxy)sulfonyl]carbamate [ No CAS ]
[ 1450833-55-2 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphoric acid In acetonitrile at 0 - 20℃; for 4h;	19.2 Step 2: Step 2: (s.e.)-((1R,2R,3S,4R)-2,3-dihydroxy-4-(2-(3-(trifluoromethylthio)-phenyl)pyrazolo[1,5-a]pyrimidin-7-ylamino)cyclopentyl)methyl sulfamate Form 1 anhydrous To a solution of tert-butyl-[({(3aR,4R,6aS)-2,2-dimethyl-6-[(2-{3-(trifluoromethylthio)phenyl}pyrazolo[1,5-a]pyrimidin-7-yl)amino]tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl}methoxy)sulfonyl]carbamate (4.0 g) in acetonitrile (20.0 mL) at 0° C. was added phosphoric acid (20.0 mL) while maintaining the temperature below 10° C. This mixture was warmed to ambient temperature and stirred for 4 hours. At this time HPLC analysis showed that <1% starting material or reaction intermediates remained. To the reaction was added ethyl acetate (20 mL) and water (20 mL). After this addition was complete saturated Na2CO3 (80.0 mL) was added until the pH was between 6-7. After stirring for 10 minutes the phases were separated and the aqueous layer was back extracted with ethyl acetate (20 mL). The organic layers were combined and dried with Na2SO4. The organic layer was then concentrated to 4 vol of ethyl acetate. The solution started to precipitate within 5 minutes. This mixture was stirred for 16 hours. The resulting white solids were collected using a filter over 5 minutes. The solid was dried in a vacuum oven under full vacuum overnight (35° C., 16 hours). This yielded (s.e.)-((1R,2R,3S,4R)-2,3-dihydroxy-4-(2-(3-(trifluoromethylthio)-phenyl)pyrazolo[1,5-a]pyrimidin-7-ylamino)cyclopentyl)methyl sulfamate anhydrous Form 1. (2.85 g, 84%). XRPD data is shown in ; DSC data is shown in ; TGA is shown in ; Raman data is shown in , 5A, 6A and 7A.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - US2013/217682, 2013, A1 Location in patent: Paragraph 0429

4
[(3aR,4R,6R,6aS)-6-amino-2,2-dumethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl]methanol hydrochloride [ No CAS ]
[ 1450833-55-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: triethylamine / 6 h / 80 °C / Inert atmosphere 2: pyridinium p-toluenesulfonate / 2-methyltetrahydrofuran / 5 h / 20 °C 3: phosphoric acid / acetonitrile / 4 h / 10 - 20 °C

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2016/69393, 2016, A1

5
((3aR,4R,6R,6aS)-2,2-dimethyl-6-((2-(3-((trifluoromethyl)thio)phenyl)pyrazolo[1,5-a]pyrimidin-7-yl)amino)tetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)methyl tert-butoxycarbonylsulfamate [ No CAS ]
[ 1450833-55-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	With phosphoric acid In acetonitrile at 10 - 20℃; for 4h;	2.6 Step 6: f R,2R3S.4R)-2J-dihvdroxy-4-((2-(3-fftrifluoromethvDthio^phenvnpyrazolori.5- a]pyrimidin-7-yl)aminokvcl nentl)methyl sulfamate Step 6: f R,2R3S.4R)-2J-dihvdroxy-4-((2-(3-fftrifluoromethvDthio^phenvnpyrazolori.5- a]pyrimidin-7-yl)aminokvcl nentl)methyl sulfamate [0165] To a solution of ((3aR,4R,6R FontWeight="Bold" FontSize="10" 6aS)-2,2-dimethyl-6-((2-(3- ((trifluoromethyl)thio)phenyl)pyrazolo[l,5-a]pyrimidin-7-yl)amino)tetrahydro-3aH- cyclopenta[d][l,3]dioxol-4-yl)methyl tert-butoxycarbonylsulfamate (2.0 g) in acetonitrile (11 mL) at 0°C was added phosphoric acid (1 1 mL) while maintaining the temperature below 10°C. This mixture was warmed to ambient temperature and stirred for 4 hours. At this time HPLC analysis showed that <1% ((3aR,4R,6R,6aS)-2,2-dimethyl-6-((2-(3 -((trifluoromethyl)thio)phenyl)pyrazolo[ 1 ,5-a]pyrimidin-7- yl)amino)tetrahydro-3aH-cyclopenta[d][l,3]dioxol-4-yl)methyl tert-butoxycarbonylsulfamate starting material or reaction intermediates remained. To the reaction was added ethyl acetate (1 1 mL) and water (11 mL) and saturated Na2C03 (10 mL) dropwise. After this addition was complete saturated Na2C03 was added until the pH was between 6-7. The phases were separated and to the organic layer was added acetonitrile (30 mL) and the mixture was concentrated on a rotovap to ~16 mL. The mixture was stirred overnight. During this time a white slurry formed. The white solids were filtered using a medium filtted filter. The solid was dried in a vacuum oven at full vacuum overnight (40°C). The reaction was then analyzed by HPLC and NMR to give ((lR,2R,3S,4R)-2,3-dihydroxy-4-((2-(3- ((trifluoromethyl)thio)phenyl)pyrazolo[ 1 ,5-a]pyrimidin-7-yl)amino)cyclopentyl)methyl sulfamate (1.5g ,84%). lH NMR (300 MHz, DMSO-c) δ ppm 1.44 - 1.61 (m, 1 H) 2.20 - 2.42 (m, 2 H) 3.78 (q, J-4.50 Hz, 1 H) 3.90 - 4.09 (m, 3 H) 4.09 - 4.22 (m, 1 H) 4.80 (d, ^5.28 Hz, 1 H) 5.03 (d, J=5.28 Hz, 1 H) 6.31 (d, J=5.57 Hz, 1 H) 7.05 (s, 1 H) 7.48 (s, 2 H) 7.62 - 7.72 (m, 1 H) 7.77 (d, J=7.92 Hz, 2 H) 8.17 (d, J=5.28 Hz, 1 H) 8.31 (dt, ^7.70, 1.43 Hz, 1 H) 8.47 (s, 1 H).

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2016/69393, 2016, A1 Location in patent: Paragraph 0164-0165

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[ CAS No. 1450833-55-2 ] {[proInfo.proName]}

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[ 1450833-55-2 ] Synthesis Path-Downstream 1~5

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