[ CAS No. 1374639-75-4 ]

Name: 1374639-75-4|7-Cyclopentyl-N,N-dimethyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide succinate|98%
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SKU: A182102
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{[proInfo.proName]} (Synonyms:Ribociclib Succinate) ,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 1374639-75-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1374639-75-4 ]

SDS Specification

Alternatived Products of [ 1374639-75-4 ]

Product Details of [ 1374639-75-4 ]

CAS No. :	1374639-75-4	MDL No. :	MFCD28167746
Formula :	C₂₇H₃₆N₈O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NHANOMFABJQAAH-UHFFFAOYSA-N
M.W :	552.63 g/mol	Pubchem ID :	57334219
Synonyms :	1. LEE011 succinate

Calculated chemistry of [ 1374639-75-4 ]

Physicochemical Properties

Num. heavy atoms :	40
Num. arom. heavy atoms :	15
Fraction Csp3 :	0.48
Num. rotatable bonds :	9
Num. H-bond acceptors :	9.0
Num. H-bond donors :	4.0
Molar Refractivity :	157.38
TPSA :	165.81 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-10.29 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.63
Log Po/w (XLOGP3) :	-0.87
Log Po/w (WLOGP) :	1.97
Log Po/w (MLOGP) :	1.06
Log Po/w (SILICOS-IT) :	1.09
Consensus Log Po/w :	1.38

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.11

Water Solubility

Log S (ESOL) :	-2.4
Solubility :	2.19 mg/ml ; 0.00397 mol/l
Class :	Soluble
Log S (Ali) :	-2.13
Solubility :	4.09 mg/ml ; 0.00741 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.51
Solubility :	0.00169 mg/ml ; 0.00000306 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	4.07

Safety of [ 1374639-75-4 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P273-P301+P310-P305+P351+P338-P314	UN#:	2811
Hazard Statements:	H301-H315-H319-H372-H400	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1374639-75-4 ]

* 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 [ 1374639-75-4 ]

[ 1374639-75-4 ] Synthesis Path-Downstream 1~10

1
[ 1003-03-8 ]
[ 1374639-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: N-ethyl-N,N-diisopropylamine / ethyl acetate / 7 h / 18 - 40 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / bis-triphenylphosphine-palladium(II) chloride / water; tetrahydrofuran / 2 h / 25 - 67 °C / Inert atmosphere 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.67 h / 25 - 60 °C / Inert atmosphere 4.1: sodium cyanide / N,N-dimethyl-formamide; tetrahydrofuran / 4.25 h / 17 - 23 °C / Inert atmosphere 5.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 4-methyl-2-pentanone / 3.25 h / 37 - 103 °C / Inert atmosphere 6.1: hydrogenchloride; water / toluene / 1.08 h / 9 - 28 °C / Inert atmosphere 6.2: Si-thiol functionalized silica gel / 6 h / 30 - 53 °C / pH 2.9 - 3.5 7.1: isopropyl alcohol / 27 - 83 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2012/115878, 2012, A1

2
[ 110-15-6 ]
[ 1211441-98-3 ]
7-cyclopentyl-N,N-dimethyl-2-[5-(piperazin-1-yl)pyridin-2-yl]amino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide succinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.9%	In isopropyl alcohol; at 27 - 83℃;Inert atmosphere;	A nitrogen-flushed, 1 L, 4-neck, round bottom flask is charged with 11.16 g (0.0945 mol, 1.05 eq.) of succinic acid (A5), and 245 g (312 mL) of 2-propanol. The suspension is stirred and warmed to 65±3 C. to obtain a clear solution. The solution is filtered while warmed through glass-fiber filter paper. The filtrate is held at 30±3 C. for addition to A4. A nitrogen-flushed 2 L, 4-neck, round bottom flask is charged with 39.11 g (0.09 mol, 1.0 eq) of 7-cyclopentyl-N,N-dimethyl-2-(5-(piperazin-1-yl)pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (A4) and 1115 g (1420 mL) of 2-propanol. The resulting suspension is stirred and heated to 80±3 C. to obtain a hazy yellow solution. The solution is cooled to 70±3 C. and filtered through a 25 g pad of Celite. The warm, filtered A4 solution is transferred to a nitrogen-flushed, 3 L, Argonaut reactor system and re-heated to 80±3 C. The succinic acid/2-propanol solution is added over 1 h maintaining 80±3 C. throughout the addition. The batch is seeded after 80% of the succinic acid solution has been added. The sample is stirred at 80±3 C. for 1 h after the addition is completed and cooled to 20±3 C. over 1 h, held 30 minutes and the solids are filtered. The filter cake is washed with 78 g (100 mL) of 2-propanol. The solids are dried at 60 C. for at least 16 h or until the LOD is 1% to afford 47.16 g (94.9%, corrected) of Compound A6 as a yellow, crystalline solid, mp 202-203 C.
78.7%	In water; acetone; at 0 - 50℃;Flow reactor; Inert atmosphere;	In a glove box under inert atmosphere (nitrogen), a solution of succinic acid (0.8 g) in water (9.6 mL) was prepared at 50 C (solution A). Ribociclib base (2.8 g) was charged in a 100 mL reactor. Solution A was added to Ribociclib base. The mixture was further diluted with water (10 mL), then succinic acid (0.72 g) was added to the mixture affording complete dissolution. Water was then distilled under vacuum to a residual volume of 10 mL at 50 C. Acetone (56 mL) was added at 50 C and precipitation was observed after addition of about 30 mL of acetone. The suspension was then cooled down to 0 C in 1 h and kept under stirring at 0 C for 30 min. The solid was isolated by filtration and washed with acetone (10 mL). Ribociclib succinate was dried under vacuum at 50 C for 18 h (2.8 g, 78.7% yield, 99.04%) purity).

Reference： [1]Patent: US2012/115878,2012,A1 .Location in patent: Page/Page column 12
[2]Patent: WO2019/40567,2019,A1 .Location in patent: Page/Page column 20-23; 26-27

3
[ 571188-59-5 ]
[ 1374639-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 4-methyl-2-pentanone / 3.25 h / 37 - 103 °C / Inert atmosphere 2.1: hydrogenchloride; water / toluene / 1.08 h / 9 - 28 °C / Inert atmosphere 2.2: Si-thiol functionalized silica gel / 6 h / 30 - 53 °C / pH 2.9 - 3.5 3.1: isopropyl alcohol / 27 - 83 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2012/115878, 2012, A1

4
[ 571189-16-7 ]
[ 1374639-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: hydrogen / palladium 10% on activated carbon / water; methanol / 0.25 h / 19 - 54 °C / 1551.49 - 2327.23 Torr / Inert atmosphere 2.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 4-methyl-2-pentanone / 3.25 h / 37 - 103 °C / Inert atmosphere 3.1: hydrogenchloride; water / toluene / 1.08 h / 9 - 28 °C / Inert atmosphere 3.2: Si-thiol functionalized silica gel / 6 h / 30 - 53 °C / pH 2.9 - 3.5 4.1: isopropyl alcohol / 27 - 83 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2012/115878, 2012, A1

5
[ 733039-20-8 ]
[ 1374639-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: tetrabutyl ammonium fluoride / bis-triphenylphosphine-palladium(II) chloride / water; tetrahydrofuran / 2 h / 25 - 67 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.67 h / 25 - 60 °C / Inert atmosphere 3.1: sodium cyanide / N,N-dimethyl-formamide; tetrahydrofuran / 4.25 h / 17 - 23 °C / Inert atmosphere 4.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 4-methyl-2-pentanone / 3.25 h / 37 - 103 °C / Inert atmosphere 5.1: hydrogenchloride; water / toluene / 1.08 h / 9 - 28 °C / Inert atmosphere 5.2: Si-thiol functionalized silica gel / 6 h / 30 - 53 °C / pH 2.9 - 3.5 6.1: isopropyl alcohol / 27 - 83 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2012/115878, 2012, A1

6
[ 1211443-61-6 ]
7-cyclopentyl-N,N-dimethyl-2-[5-(piperazin-1-yl)pyridin-2-yl]amino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide succinate [ No CAS ]

Reference： [1]Patent: US2012/115878,2012,A1

7
[ 1374639-76-5 ]
[ 1374639-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.67 h / 25 - 60 °C / Inert atmosphere 2.1: sodium cyanide / N,N-dimethyl-formamide; tetrahydrofuran / 4.25 h / 17 - 23 °C / Inert atmosphere 3.1: caesium carbonate / palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 4-methyl-2-pentanone / 3.25 h / 37 - 103 °C / Inert atmosphere 4.1: hydrogenchloride; water / toluene / 1.08 h / 9 - 28 °C / Inert atmosphere 4.2: Si-thiol functionalized silica gel / 6 h / 30 - 53 °C / pH 2.9 - 3.5 5.1: isopropyl alcohol / 27 - 83 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US2012/115878, 2012, A1

8
[ 1374639-77-6 ]
7-cyclopentyl-N,N-dimethyl-2-[5-(piperazin-1-yl)pyridin-2-yl]amino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide succinate [ No CAS ]

Reference： [1]Patent: US2012/115878,2012,A1

9
[ 110-15-6 ]
[ 1211441-98-3 ]
7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide succinate salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97.1%	In tetrahydrofuran; at 25 - 70℃;	Tetrahydrofuran (120 mL) and Ribociclib (3.0g, 0.0069 moles) were charged into 250 mL 4 neck round bottomed flask at 30±5C and stirred for 5-10 min. to get cream colored suspension. Reaction mass was heated to 65-70C and stirred for 15 min to get clear solution. The solution of succinic acid (0.85g, 0.0072moles) in tetrahydrofuran (60 mL) was added to the above reaction mass dropwise through addition funnel at 65-70C. After addition of succinic acid solution, pale yellow coloured suspension was formed in the reaction mass and was stirred for lh. Then the reaction mass was cooled to 25-35C and stirred for lh. Product was filtered off under suction. Product was dried in vacuum oven at 65-70C to afford title compound as cream coloured solid. Weight of the product: 3.7g (97.1% by theory) as cream coloured solid. Purity by HPLC > 99.0%. (0115) The obtained crystalline compound is characterized by PXRD as illustrated in figure- 1.
95%	In isopropyl alcohol; at 85℃; for 0.5h;	dd 100g of Rebizzini (Formula 4), 1200g of isopropanol to a 2L three-necked flask, heat to 85 C, while 28.53gSuccinic acid was added to 240 g of isopropanol and dissolved by heating. Then, a succinic acid/isopropanol mixed solution was added dropwise to a 2 L three-necked flask.After the addition is completed, a large amount of solid is precipitated, stirred for 30 minutes, naturally cooled to room temperature, stirred for 2 to 3 hours, filtered, and used less.The mixture was washed with cold isopropanol and dried under reduced pressure at 60 C for 24 hours. Resino succinate (Formula 5) dry product 120g, yield 95.0%, byThe purity by HPLC (area normalization method) was 99.91%, the maximum single impurity was 0.06%, and the palladium residue was 0.2 ppm.
90%	In methanol; dichloromethane; at 20 - 30℃;	Method-1 Ribociclib (2 g) and succinic acid (600 mg) were added in the solution of dichloromethane (30 mL) and methanol (10 mL) at 20-30C. Reaction mixture was stirred for 5 0-60 mm followed by addition of diisopropyl ether (20 mL) at the same temperature. The reaction mixture was stirred for 4-5 hrs. The solid soformed, was collected by filtration and dried to give Ribociclib succinate form-N (2.3g).Yield: 90%; HPLC Purity: 99.76%

	In methanol; acetonitrile; at 50℃; for 48h;	10141] 30.7 mg of the non-hydrate form (prepared according to patent CN103201275A) was added into 2.2 mL of acetonitrile/methanol (v/v=10/1), then stirred at 50 C. for 48 hours, until solids precipitate out.The XRPD data of the mono-succinate Form Iproduced in this example is listed in Table 4 and the XRPDpattern was displayed in FIG. 5.The ?H NMR spectrum of the mono-succinateForm I produced in this example is displayed in FIG. 6. ?HNMR data is shown as following: ?H NMR (400 MHz, DM50) oe 9.33 (s, 1H), 8.76(s, 1H), 8.16 (d, J=9.1 Hz, 1H), 8.00 (d, J=2.9 Hz, 1H), 7.45(dd, J9.1, 3.0 Hz, 1H), 6.60 (s, 1H), 4.79-4.68 (m, 1H),3.16-3.00 (m, 14H), 2.34 (s, 4H), 1.98 (s, 4H), 1.64 (d, J=5.5Hz, 2H). ?H NMR results show that Form I is a monosuccinate of compound I.DSC curve of mono-succinate Form I was displayed in FIG. 7. Form I is an anhydrate, the DSC data showed an endothermic peak at 197 C. (onset temperature).TGA curve of mono-succinate Form I was displayed in FIG. 8. The TGA data showed 2.0% weight loss up to 178 C
435 mg	In isopropyl alcohol; at 25 - 75℃; for 16h;	Ribociclib free base (500 mg) was added to iso-propanol (30 mL) and stirred at 75C for 25 minutes to obtain a reaction mixture. Iso-propanol (2.5 mL) with succinic acid (150 mg) was added to the reaction mixture and stirring was continued at 75C for 4 hours. Iso-propanol (10 mL) was again added to the reaction mixture and the mixture was stirred at ambient temperature for 12 hours to obtain a solid. The solid obtained wascollected by filtration and then dried at 50C under vacuum for 10 hours to obtain the titlecompound. Yield: 435 mg
1.2 g	In water; at 25 - 55℃;	Succinic acid (0.285 g, 0.0024mol) was charged into a reaction flask containing water (5.0 rnL) at 25-30C. Reaction mass was heated to 50-55C. Charged Ribociclib base (1.0 g, 0.0023mol) at 50-55C and stirred for 2hours minutes at 50-55C. Reaction mass filtered through 0.22 micron filter and washed with water (2.0 mL). Concentrated the reaction mass under vacuum at 65-70C with Heptane, isolated the product. Dried the material under vacuum at 55-60C for 12- 15 hours.Yield: 1.2 g.
	In 1,4-dioxane; at 25 - 30℃; for 4h;	To a suspension of ribociclib base (1.0 g) in l,4-dioxane (30ml) was added succinic acid (0.28g ) at 25-30C. The reaction mixture was stirred at 25-30C for 4 hr. The solids were isolated by filtration and dried at 50C under vacuum, resulted the title compound (T l5g) and identified by XRD as Form-C2, as presented in figure 1.
	In isopropyl alcohol;	Weigh 5.0mg succinic acid in 1.0mL isopropanol, weigh 20.0mg of compound (I) suspended in 1.0mL isopropanol,A solution of succinic acid in isopropanol was added dropwise, filtered, and the filter cake was dried in vacuum at 40 C to obtain a solid.

Reference： [1]Patent: WO2019/142206,2019,A1 .Location in patent: Page/Page column 16-17
[2]Patent: CN109400612,2019,A .Location in patent: Paragraph 0055-0057
[3]Patent: WO2019/82143,2019,A1 .Location in patent: Page/Page column 43; 44
[4]Patent: US2017/342075,2017,A1 .Location in patent: Paragraph 0141; 0142; 0143; 0144; 0145; 0146; 0147
[5]Patent: WO2019/111160,2019,A1 .Location in patent: Page/Page column 2; 14; 15
[6]Patent: WO2019/123364,2019,A1 .Location in patent: Page/Page column 15; 16
[7]Patent: WO2019/167068,2019,A1 .Location in patent: Page/Page column 33
[8]Patent: CN110964017,2020,A .Location in patent: Paragraph 0151-0153

10
[ 1374639-78-7 ]
7-cyclopentyl-N,N-dimethyl-2-[5-(piperazin-1-yl)pyridin-2-yl]amino}-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide succinate [ No CAS ]

Reference： [1]Patent: WO2019/40567,2019,A1

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[ 1374639-75-4 ]

A288696[ 1211441-98-3 ]

7-Cyclopentyl-N,N-dimethyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Reason: Free-salt

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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

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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

[ CAS No. 1374639-75-4 ]

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Physicochemical Properties

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[ 1374639-75-4 ] Synthesis Path-Downstream 1~10

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