[ CAS No. 827022-33-3 ] {[proInfo.proName]}

Name: 827022-33-3|6-Acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one 2-hydroxyethanesulfonate|98%
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Quality Control of [ 827022-33-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 827022-33-3 ]

SDS Specification

Alternatived Products of [ 827022-33-3 ]

Product Details of [ 827022-33-3 ]

CAS No. :	827022-33-3	MDL No. :
Formula :	C₂₆H₃₅N₇O₆S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LYYVFHRFIJKPOV-UHFFFAOYSA-N
M.W :	573.66	Pubchem ID :	11478676
Synonyms :	PD 0332991 isethionate	Chemical Name :	6-Acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one 2-hydroxyethanesulfonate

Calculated chemistry of [ 827022-33-3 ]

Physicochemical Properties

Num. heavy atoms :	40
Num. arom. heavy atoms :	16
Fraction Csp3 :	0.5
Num. rotatable bonds :	7
Num. H-bond acceptors :	10.0
Num. H-bond donors :	4.0
Molar Refractivity :	159.46
TPSA :	188.02 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 :	No
Log Kp (skin permeation) :	-11.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.44
Log Po/w (XLOGP3) :	-2.04
Log Po/w (WLOGP) :	2.15
Log Po/w (MLOGP) :	0.48
Log Po/w (SILICOS-IT) :	2.51
Consensus Log Po/w :	1.11

Druglikeness

Lipinski :	2.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.17

Water Solubility

Log S (ESOL) :	-1.95
Solubility :	6.5 mg/ml ; 0.0113 mol/l
Class :	Very soluble
Log S (Ali) :	-1.38
Solubility :	23.8 mg/ml ; 0.0414 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-6.49
Solubility :	0.000186 mg/ml ; 0.000000324 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.17

Safety of [ 827022-33-3 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P264-P270-P301+P310-P321-P330-P405-P501	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 827022-33-3 ]

* 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 [ 827022-33-3 ]

[ 827022-33-3 ] Synthesis Path-Downstream 1~7

1
[ 571190-30-2 ]
[ 107-36-8 ]
PD 0332991 isethionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.8%	In methanol; at -8 - 20℃;Conversion of starting material;	EXAMPLE 7 Preparation of A MONO-ISETHIONATE salt of 6-ACETYL-8-CVCLOPENTYL-5-METHYL-5- IPERAZIN-1-VL-PVRIDIN-2-VLAMINO)-8H-PVRIDOF2,. 3-DLPVRIMIDIN-7-ONE (Form B) The free base (Formula 1, 0. 895 mg, 2 MMOL) was mixed with 10 mL of MeOH and seeded with 33 mg of A MONO-ISETHIONATE SALT OF THE COMPOUND OF FORMULA L (FORM B). THEN 5.6 mL of A 0. 375 M solution of isethionic acid in MeOH (2. 1 MMOL) was added in 10 even portions over 75 min time period. The mixture was stirred for an additional hour and a sample was TAKEN FOR PXRD ANALYSIS. IT CONFIRMED FORMATION OF CRYSTALLINE FORM B. THE MIXTURE WAS stirred at RT overnight and another PXRD was taken. There was no change in the crystal form. The mixture was cooled in a refrigerator AT-8C overnight, filtered, and dried at 50C in a vacuum oven to give 1.053 g (91.8 % of theory) of the above-named compound (Form B). HPLC-99.8 %, CHNS, H-NMR, IR are consistent with the structure, PXRD-Form B.
52.5%	In methanol; at 20℃; for 3h;	5L three bottles, put into 290.0g (0.65mol) free base, 1.2L methanol, stirred at room temperature, the moment after dropping 98.2g isethionic (0.78mol) and 500mL methanol mixture, the suspension system gradually became clear there are large amount of solid precipitated, continued stirring for 3 hours at room temperature, suction filtered, the filter cake rinsed with methanol, 45 blast drying to give a pale yellow solid, constant weight 196.0g, a yield of 52.5%.
	In methanol; water;pH 5.2;	EXAMPLE 4 Preparation of A mono-isethionate salt of 6-ACETVL-8-CVCLOPENTYL-5-METHYL-2- (5- PIPERAZIN-1-YL-PYRIDIN-2-VLAMINO)-8H-PVRIDOF2. 3-DLPVRIMIDIN-7-ONE (Form B) To A slurry of 6-ACETYL-8-CYCLOPENTYL-5-METHYL-2- (5-PIPERAZIN-1-YL-PYRIDIN-2-YLAMINO)- 8H-PYRIDO [2, 3-DIPYRIMIDIN-7-ONE (7.0 g, 15.64 MMOL, prepared as in Example 3 following contact with NaOH) dispersed in 250 mL of water was added drop-wise 30 mL OF A 0. 52 M solution of isethionic acid in MeOH (15. 64 MMOL) to A pH of 5. 2. The solution was filtered through A glass filter (fine) and the clear solution was freeze-dried to give 9. 4 G of the amorphous salt. The amorphous salt (3. 16 g) was mixed with 25 mL of MEC) H AND AFTER almost complete dissolution A new precipitate formed. Another 25 mL of MeOH was added and the mixture was stirred at 46C to 49C for four hours. The mixture was slowly cooled to 32C and put in a cold room (+4C) overnight. A sample was taken for PXRD, which indicated formation of Form B. The mixture was filtered and the precipitate was dried overnight at 50C in a vacuum oven. This furnished 2.92 G of the mono-isethionate salt of the compound of Formula 1 in 92 % yield.

In methanol; water;pH 5.2;

Preparation 4 Preparation of a mono-isethionate salt of 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (Form B) To a slurry of 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (7.0 g, 15.64 mmol, prepared as in Example 3 following contact with NaOH) dispersed in 250 mL of water was added drop-wise 30 mL of a 0.52 M solution of isethionic acid in MeOH (15.64 mmol) to a pH of 5.2. The solution was filtered through a glass filter (fine) and the clear solution was freeze-dried to give 9.4 g of the amorphous salt. The amorphous salt (3.16 g) was mixed with 25 mL of MeOH and after almost complete dissolution a new precipitate formed. Another 25 mL of MeOH was added and the mixture was stirred at 46 C. to 49 C. for four hours. The mixture was slowly cooled to 32 C. and put in a cold room (+4 C.) overnight. A sample was taken for PXRD, which indicated formation of Form B. The mixture was filtered and the precipitate was dried overnight at 50 C. in a vacuum oven. This furnished 2.92 g of the mono-isethionate salt of the compound of Formula 1 in 92% yield. HPLC-99.25%, PXRD-Form B, CHNS, H-NMR were consistent with the structure.

Reference： [1]Patent: WO2005/5426,2005,A1 .Location in patent: Page/Page column 23
[2]Patent: CN105541832,2016,A .Location in patent: Paragraph 0050; 0051; 0052; 0053; 0054; 0055; 0069-0071
[3]Patent: WO2005/5426,2005,A1 .Location in patent: Page/Page column 22
[4]Patent: US2005/222163,2005,A1 .Location in patent: Page/Page column 26

2
tert‑butyl 4‑(6‑((6‑(1‑butoxyvinyl)‑8‑cyclopentyl‑5‑methyl‑7‑oxo‑7,8‑dihydropyrido[2,3‑d]pyrimidin‑2‑yl)amino)pyridin‑3‑yl)piperazine‑1‑carboxylate [ No CAS ]
[ 107-36-8 ]
PD 0332991 isethionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		EXAMPLE 12 Preparation of a mono-isethionate salt of 6-ACETVL-8-CYCLOPENTYL-5-METHYL-2- 5- PIPERAZIN-1-VL-VRIDIN-2-YLAMINO)-8H-PVRIDO [2, 3-DLPVRIMIDIN-7-ONE (FORM B) A 22-L, three-necked, round-bottomed flask, equipped with a mechanical stirrer, A thermocouple, and A nitrogen inlet/outlet vented through A silicone oil bubbler was placed under a nitrogen atmosphere and charged with 4-{6-[6-(1-butoxy-vinyl)-8-cyclopentyl-5- methyl-7-oxo-7, 8-DIHYDRO-PYRIDO [2, 3-DJPYRIMIDIN-2-YLAMINO]-PYRIDIN-3-YL}-PIPERAZINE-1- carboxylic acid TERT-BUTYL ester (725 g, 1.20 mol, prepared as in Example 11) and MEOH (14 L). The slurry was stirred at RT as it was charged with a solution of isethionic acid (530 g, 4.20 mol, prepared as in Example 10), MEOH (1.5 L), and water (70 mL, 3.89 MOL). The resulting slurry was heated to 55C over 30 minutes and then stirred at 55C for 30 minutes. A solution of 175 g (1.73 mol) of Et3N (ALDRICH) in 200 mL of MeOH was charged to the slurry as it was cooled to 30C. The slurry was held at 30C as a solution of 128 g (1.26 mol) of Et3N in 2 L of MEOH was added dropwise over 6 hours. The resulting slurry was sampled to determine crystal form (Form B). The slurry was cooled and held at 5C for 15 minutes and was subsequently filtered through a coarse-fritted filter. The resulting filter cake was washed with multiple washes of 200 mL of COLD MEOH. The solid product was dried at 55T under vacuum to yield 710 g (91 % yield) of the title compound as yellow crystals.
91%		Preparation 12 Preparation of a mono-isethionate salt of 6-acetyl-8-cyclopentyl-5-methyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-one (Form B) A 22-L, three-necked, round-bottomed flask, equipped with a mechanical stirrer, a thermocouple, and a nitrogen inlet/outlet vented through a silicone oil bubbler was placed under a nitrogen atmosphere and charged with 4-{6-[6-(1-butoxy-vinyl)-8-cyclopentyl-5-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-2-ylamino]-pyridin-3-yl}-piperazine-1-carboxylic acid tert-butyl ester (725 g, 1.20 mol, prepared as in Example 11) and MeOH (14 L). The slurry was stirred at RT as it was charged with a solution of isethionic acid (530 g, 4.20 mol, prepared as in Example 10), MeOH (1.5 L), and water (70 mL, 3.89 mol). The resulting slurry was heated to 55 C. over 30 minutes and then stirred at 55 C. for 30 minutes. A solution of 175 g (1.73 mol) of Et3N (ALDRICH) in 200 mL of MeOH was charged to the slurry as it was cooled to 30 C. The slurry was held at 30 C. as a solution of 128 g (1.26 mol) of Et3N in 2 L of MeOH was added dropwise over 6 hours. The resulting slurry was sampled to determine crystal form (Form B). The slurry was cooled and held at 5 C. for 15 minutes and was subsequently filtered through a coarse-fritted filter. The resulting filter cake was washed with multiple washes of 200 mL of cold MeOH. The solid product was dried at 55 C. under vacuum to yield 710 g (91% yield) of the title compound as yellow crystals. It is to be understood that the above description is intended to be illustrative and not restrictive. Many embodiments will be apparent to those of skill in the art upon reading the above description. The scope of the invention should, therefore, be determined not with reference to the above description, but should instead be determined with reference to the appended claims, along with the full scope of equivalents to which such claims are entitled. The disclosures of all articles and references, including patents, patent applications, and patent publications, are incorporated herein by reference in their entirety and for all purposes.
	With methanol; water; at 55 - 60℃; for 6h;	Example 6: Preparation of e-acetyl-delta-cyclopentyl-S-methyl^^S-piperazin-i-yl-pyridin^-ylaminoJ-delta/-/- pyrido[2,3-c(]pyrimidin-7-one11.6 g (1.00 eq, 19.2mmol) of-intermediate 5, water- (10.1 equiv; 193 mmoles; 3.48 ml 3.48 g) and methanol (3.62 moles; 146 ml 116 g) were combined and heated to 55-600C. lsethionic acid was added slowly until a clear solution was obtained; 3.3g isethionic acid solution was necessary to reach this end point. The resulting clear orange solution was filtered through paper and rinsed through with 20ml methanol, after which the filtrate was reheated to 55-600C and the remaining isethionic acid was added (a total of 9.93g was added). The reaction mixture precipitated and thickened for 6 hours.after which it was cooled and held at 30-350C while triethylamine ( 2.92g; 28.8mmoles) was added slowly as a 10% solution in methanol over 12hrs. About halfway through the addition of triethylamine, desired polymorphic seeds were added to help formation of the desired polymorph. The resulting slurry was cooled and held at 5C for 15 minutes and the crystals were filtered and washed with methanol. The solid product was dried in vacuo at 550C to obtain 11 g of yellow crystals of the title compound.

Reference： [1]Patent: WO2005/5426,2005,A1 .Location in patent: Page/Page column 25; 26
[2]Patent: US2005/222163,2005,A1 .Location in patent: Page/Page column 28
[3]Patent: WO2008/32157,2008,A2 .Location in patent: Page/Page column 28

3
[ 571188-59-5 ]
[ 827022-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: isopropyl chloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Large scale 1.2: 70 °C / Large scale 2.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 0.5 h / 20 °C / Inert atmosphere 2.2: 3 h / 80 - 100 °C / Inert atmosphere 3.1: methanesulfonic acid / water; acetone / 0.5 h / 45 - 55 °C 4.1: methanol / 3 h / 20 °C

Reference： [1]Current Patent Assignee: NANJING NMG ADDS - CN105541832, 2016, A

4
[ 1016636-76-2 ]
[ 827022-33-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: isopropyl chloride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Large scale 1.2: 70 °C / Large scale 2.1: N-ethyl-N,N-diisopropylamine / butan-1-ol / 0.5 h / 20 °C / Inert atmosphere 2.2: 3 h / 80 - 100 °C / Inert atmosphere 3.1: methanesulfonic acid / water; acetone / 0.5 h / 45 - 55 °C 4.1: methanol / 3 h / 20 °C

Reference： [1]Current Patent Assignee: NANJING NMG ADDS - CN105541832, 2016, A

5
[ 571188-82-4 ]
PD 0332991 isethionate [ No CAS ]

Reference： [1]Patent: CN105541832,2016,A

6
[ 866084-31-3 ]
[ 827022-33-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: tert‑butyl 4‑(6‑((6‑(1‑butoxyvinyl)‑8‑cyclopentyl‑5‑methyl‑7‑oxo‑7,8‑dihydropyrido[2,3‑d]pyrimidin‑2‑yl)amino)pyridin‑3‑yl)piperazine‑1‑carboxylate With 2-hydroxyethanesulfonic acid; water In methanol at 55℃; for 0.5h; Stage #2: With triethylamine In methanol at 30℃;	3 Preparation of palbociclib isethionate A solution of tert-butyl 4-(6-[6-(1-butoxyethenyl)-8-cyclopentyl-5-methyl-7-oxo-7H,8H-pyrido[2,3-d]pyrimidin-2-yl]amino}pyridin-3-yl)piperazine-1-carboxylate(7.25 g, 12.0 mmoL) was added to methanol(140 mL), and then a mixed solution of isethionic acid (5.3 g, 42.0 mmol), methanol (15.0 mL) and water (0.70 mL, 38.9 mmoL) was slowly added dropwise. After the addition is completed,The system was heated to 55 ° C and stirred at this temperature for 30 minutes.A solution of triethylamine (1.8 g, 13.0 mmoL) in methanol (3.0 mL) was added dropwise,During this process, the temperature of the reaction system dropped to 30 ° C.Triethylamine (1.3 g, 12.6 mmoL) in methanol (20.0 mL) was added dropwise at 30 ° C, and the dropwise addition was completed over 6.0 hours. Stir overnight.Placed at 4 ° C for 1.0 hour, filtered,The solid was washed with methanol (2.0 mL)Vacuum drying at 55 ° C for 1.0 hour afforded 6.8 g of pure yellow solid in 87% yield.

Reference： [1]Current Patent Assignee: SUZHOU GUOKUANG PHARMACEUTICAL TECH - CN106397431, 2017, A Location in patent: Paragraph 0097; 0098; 0099; 0100

7
[ 827022-33-3 ]
[ 571190-30-2 ]

Yield	Reaction Conditions	Operation in experiment
0.68 g	With sodium hydrogencarbonate In water at 20℃; for 4h;	6 Preparation of palbociclib Form A and Form C mixed crystals The product from Example 3 (0.72 g) was added slowly to a saturated solution of sodium bicarbonate (13.0 mL) andDistilled water (15.0 mL) and stirred at room temperature for 4.0 hours. Filter, solid with distilled water (3 x 5.0 mL)Washed and dried to constant weight in an air bath at 50 ° C to give 0.68 g of a pure yellow solid.

Reference： [1]Current Patent Assignee: SUZHOU GUOKUANG PHARMACEUTICAL TECH - CN106397431, 2017, A Location in patent: Paragraph 0117; 0118; 0119; 0120

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[ 827022-33-3 ]

A295334[ 571190-30-2 ]

6-Acetyl-8-cyclopentyl-5-methyl-2-((5-(piperazin-1-yl)pyridin-2-yl)amino)pyrido[2,3-d]pyrimidin-7(8H)-one

Reason: Free-salt

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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
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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. 827022-33-3 ] {[proInfo.proName]}

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[ 827022-33-3 ] Synthesis Path-Downstream 1~7

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