[ CAS No. 1374639-77-6 ] {[proInfo.proName]}

Name: 1374639-77-6|(2-Chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol|98%
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SKU: A247616
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Quality Control of [ 1374639-77-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1374639-77-6 ]

CAS No. :	1374639-77-6	MDL No. :	MFCD29072793
Formula :	C₁₂H₁₄ClN₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ADHCEFBFOBDYEC-UHFFFAOYSA-N
M.W :	251.71	Pubchem ID :	86693573
Synonyms :

Calculated chemistry of [ 1374639-77-6 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	67.04
TPSA :	50.94 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.55
Log Po/w (XLOGP3) :	1.9
Log Po/w (WLOGP) :	2.54
Log Po/w (MLOGP) :	1.72
Log Po/w (SILICOS-IT) :	2.31
Consensus Log Po/w :	2.2

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.86
Solubility :	0.35 mg/ml ; 0.00139 mol/l
Class :	Soluble
Log S (Ali) :	-2.59
Solubility :	0.643 mg/ml ; 0.00256 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.32
Solubility :	0.12 mg/ml ; 0.000476 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.03

Safety of [ 1374639-77-6 ]

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 [ 1374639-77-6 ]

* 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.

Upstream synthesis route of [ 1374639-77-6 ]
Downstream synthetic route of [ 1374639-77-6 ]

[ 1374639-77-6 ] Synthesis Path-Upstream 1~4

1
[ 1374639-77-6 ]
[ 124-40-3 ]
[ 1211443-61-6 ]

Reference： [1] Patent: US2012/115878, 2012, A1, . Location in patent: Page/Page column 7-8

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[ 1374639-76-5 ]
[ 1374639-77-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	With trifluoroacetic acid In tetrahydrofuran at 29 - 60℃; for 12 h; Inert atmosphere	A solution of compound (3).(5g, 19.9 mmol) in THF (50 mL) was stirred at 29 °C undernitrogen atmosphere, tetrabutylammonium fluoride solution1.0M in THF (45 mL) was added to the mixture and heatedat 60 °C for 12 hours. Progress of the reaction was monitoredby TLC. After completion of the reaction, the resultingmixture was concentrated under vacuum and residue wasdissolved in 2-propanol (10 mL) at 50°C. The clear solutionwas cooled to 29°C, with slowly charged water (75 mL) andstirred for 4 hours. Precipitate was filtered and washed withwater, followed by being dried at 50°C under vacuum toobtain compound (4). Brown solid, Yield: 68percent, mp. 173-175 °C. 1H NMR (400 MHz, DMSO-d6): 1.64-1.65 (m, 2H, -CH2), 1.98-2.03 (m, 4H, CH2), 2.22-2.29 (m, 2H, CH2), 4.67(d, 2H, J=5.12 Hz, CH2OH), 4.87-4.89 (m, 1H, -NH-CH-),5.52 (s, 1H, CH2OH), 6.55 (s, 1H, Ar-H), 8.82 (s, 1H, Ar-H).13C NMR (75.46 MHz, DMSO-d6): 152.3, 151.5, 150.9,144.7, 118.21, 98.5, 56.4, 52.3, 30.7, 24.9. ESI-HRMS (m/z):Calcd. for C12H14ClN3O: 251.7129. Found: m/z 251.8001[M+].
20.2 g	With tetrabutyl ammonium fluoride In tetrahydrofuran at 25 - 60℃; for 4.16667 h;	To a solution of 3-(2-chloro-4-(cyclopentylamino)pyrimidin-5-yl)prop-2-yn-l-ol (27 g) in tetrahydrofuran (270 mL) was added a solution of tetra butyl ammonium fluoride in tetrahydrofuran (1M , 268 mL) at 25-30 °C and stirred for 10 minutes at the same temperature. The reaction mass was then heated to 60 °C and stirred for 4 hours at the same temperature. The reaction mass was then cooled to 25-30 °C and evaporated under reduced pressure at 45 °C. Residue obtained from the evaporation was dissolved in 2-propanol (270 mL) and stirred for 15 minutes at 25-30 °C. Water (270 mL) was added to the above solution and again stirred for 30 minutes at 20 °C. Resulting solid compound was then filtered, washed with water (2 x 30 mL) followed by n- hexane (100 mL) and methyl tert-butyl ether (100 mL), dried for 16 hours at 50 °C to afford the title compound. (0160) Yield: 20 2 g; Purity by HPLC: 95 25 percent

Reference： [1] Combinatorial Chemistry and High Throughput Screening, 2017, vol. 20, # 8, p. 703 - 712
[2] Patent: US2012/115878, 2012, A1, . Location in patent: Page/Page column 7
[3] Patent: WO2018/51280, 2018, A1, . Location in patent: Page/Page column 20

3
[ 1003-03-8 ]
[ 1374639-77-6 ]

Reference： [1] Patent: US2012/115878, 2012, A1,
[2] Combinatorial Chemistry and High Throughput Screening, 2017, vol. 20, # 8, p. 703 - 712

4
[ 733039-20-8 ]
[ 1374639-77-6 ]

Reference： [1] Patent: US2012/115878, 2012, A1,
[2] Combinatorial Chemistry and High Throughput Screening, 2017, vol. 20, # 8, p. 703 - 712

[ 1374639-77-6 ] Synthesis Path-Downstream 1~88

1
[ 1003-03-8 ]
[ 1374639-77-6 ]

Reference： [1]Patent: US2012/115878,2012,A1
[2]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712
[3]Patent: EP3434676,2019,A1

2
[ 1374639-77-6 ]
[ 124-40-3 ]
[ 1211443-61-6 ]

Yield	Reaction Conditions	Operation in experiment
75.1%		Step 3: Synthesis of 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d] pyrimidine-6-carboxamide A tetrahydrofuran solution of dimethylamine (15.8 mL, 2.0 M) and sodium cyanide (0.39 g, 7.9 mmol) were added to a solution of (2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol (2.0 g, 7.9 mmol) in N,N-dimethylformamide (15 mL). The mixed solution was stirred at room temperature to react for 4 min. Active manganese dioxide (30.9 g, 355.5 mmoL) was added in batches to the reaction mixture. The reaction mixture was further stirred at room temperature for 12 h, and filtered. The filtrate was poured into water (100 mL), and extracted with ethyl acetate (100 mL*2). The organic phase was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether: ethyl acetate=4:1) to obtain 2-chloro-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (1.75 g, yield: 75.1 %). 1H NMR (400 MHz, DMSO-d6): 8.95 (1H,s), 6.78 (1H, s), 4.78 (1H, quiv, J=8.8 Hz), 3.03 (3H, s), 2.99 (3H, s), 2.16-2.26 (2H, m), 1.87-2.02 (4H, m), 1.56-1.66 (2H, m).
	With sodium cyanide; In tetrahydrofuran; N,N-dimethyl-formamide; at 17 - 23℃; for 4.25h;Inert atmosphere;	A dry, nitrogen-flushed ACE-100L Reaction vessel is charged with 97.3 g of sodium cyanide, 2,500 g of (2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-c]pyrimidin-6-yl)methanol, A1c, 16,680 g (19.5 L) of dimethylamine, A1a (2.0M solution in THF), and 28,320 g (30.0 L) of anhydrous N,N-dimethylformamide. The mixture is stirred at 20±3 C. for 15 min. 2.06 kg of manganese(IV) oxide is then added. The dark slurry is stirred for 30 min and 12.36 Kg of manganese (IV) oxide is added in three portions (1st portion: 2.06 kg; 2nd portion: 4.12 g, and 3rd portion: 6.18 kg) every 30 min. After the last portion has been added, the sample is held for 1 h and then 6.18 kg of manganese(IV) oxide is added. The sample is held for 1 h. The reaction mixture is then sampled. The reaction is considered complete if the starting material, A1c is ?1.0±0.5% as determined by HPLC analysis. The reaction mixture is then filtered through a pad of celite to remove manganese (IV) oxide. The reactor and cake are rinsed with 23 L of ethyl acetate. The filtrate and distil are combined under reduced pressure (45±3 C., 20 mbar) to remove THF, dimethylamine and ethyl acetate. The sample is further distilled under reduced pressure (70±5 C., 5 mbar) to remove DMF. The concentrate is diluted with 35 L of ethyl acetate. The resulting dark solution is washed with aqueous ferrous sulfate solution (1 kg of FeSO4.7H2O in 14 L of water), 15 L of water and finally 15 L of 10% aqueous NaCl solution. The phases are separated after each wash. The organic phase is distilled (45 C., 50 mbar) to azeotropically remove water. The resulting crude A1 (2,788 g of a dark, thick, semi-solid residue) can be used directly in the next step.; 10 g of crude A1 and 9 mL of 1-propanol are warmed gently until a homogeneous, dark solution is obtained. The solution is cooled to 25+/-3 C. and 30 to 40 mL of hexane is slowly added. The sample is seeded and stirred until crystals are observed. An additional 50 to 60 mL of hexane is slowly added. The total volume of hexane added is about 90 mL. The slurry is held at 22+/-3 C. for 2 h, then cooled to 4 C. and held for an additional 2 h. The solids are filtered. The flask and filter cake are washed with hexane as needed. The filter cake is dried at 50 C., 50 mbar to afford 6.35 g of purified A1 as a light tan, crystalline solid. Recovery: 63.5%.Method 2:A solution of 10 g of crude A1 in 10 mL of EtOAc is prepared and loaded onto a 100 g bed of silica gel. The column is eluded with 300 mL of EtOAc/hexane (2/8) and the eluant is disgarded. The column is then elude with 800 mL of EtOAc/hexane (5/5) and the eluant is collected (No.2) for isolation of the product. The eluant (No.2) is concentrated to thin oil. 100 mL of hexane is slowly added and the sample is stirred at 22+/-3 C. for 2 h. The sample is cooled to 4 C. and held an additional 2 h. The solids are filtered. The flask and filter cake are washed with hexane as needed. The filter cake is dried at 50 C., 50 mbar to afford 6.05 g of purified A1 as a light tan, crystalline solid. Recovery 60.5%.

Reference： [1]Patent: EP3434676,2019,A1 .Location in patent: Paragraph 0109; 0114; 0115
[2]Patent: US2012/115878,2012,A1 .Location in patent: Page/Page column 7-8

3
[ 733039-20-8 ]
[ 1374639-77-6 ]

Reference： [1]Patent: US2012/115878,2012,A1
[2]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712
[3]Patent: EP3434676,2019,A1

4
[ 1374639-76-5 ]
[ 1374639-77-6 ]

Yield	Reaction Conditions	Operation in experiment
81.5%	With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 70℃; for 12h;	Step 2: (2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol Tetrabutylammonium fluoride trihydrate (18.8 g, 59.6 mmol) was added to a solution of 3-(2-chloro-4-(cyclopentylamino)pyrimidin-5-yl)prop-2-yn-1-ol (6.0 g, 23.8 mmol) in tetrahydrofuran (150 mL). The mixed solution was kept at 70 C to react for 12 h. The reaction mixture was cooled, water (150 mL) was added thereto, and the resulting mixture was extracted with ethyl acetate (150 mL*2). The organic phase was dried with anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (petroleum ether: ethyl acetate=10:1) to obtain (2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d] pyrimidin-6-yl)methanol (4.89 g, yield: 81.5 %). 1H NMR (400 MHz, CDCl3): 8.65 (1H, s), 6.43 (1H, s), 4.87-4.95 (1H, m), 4.82 (2H, s), 2.35-2.43 (2H, m), 1.99-2.19 (6H, m).
68%	With trifluoroacetic acid; In tetrahydrofuran; at 29 - 60℃; for 12h;Inert atmosphere;	A solution of compound (3).(5g, 19.9 mmol) in THF (50 mL) was stirred at 29 C undernitrogen atmosphere, tetrabutylammonium fluoride solution1.0M in THF (45 mL) was added to the mixture and heatedat 60 C for 12 hours. Progress of the reaction was monitoredby TLC. After completion of the reaction, the resultingmixture was concentrated under vacuum and residue wasdissolved in 2-propanol (10 mL) at 50C. The clear solutionwas cooled to 29C, with slowly charged water (75 mL) andstirred for 4 hours. Precipitate was filtered and washed withwater, followed by being dried at 50C under vacuum toobtain compound (4). Brown solid, Yield: 68%, mp. 173-175 C. 1H NMR (400 MHz, DMSO-d6): 1.64-1.65 (m, 2H, -CH2), 1.98-2.03 (m, 4H, CH2), 2.22-2.29 (m, 2H, CH2), 4.67(d, 2H, J=5.12 Hz, CH2OH), 4.87-4.89 (m, 1H, -NH-CH-),5.52 (s, 1H, CH2OH), 6.55 (s, 1H, Ar-H), 8.82 (s, 1H, Ar-H).13C NMR (75.46 MHz, DMSO-d6): 152.3, 151.5, 150.9,144.7, 118.21, 98.5, 56.4, 52.3, 30.7, 24.9. ESI-HRMS (m/z):Calcd. for C12H14ClN3O: 251.7129. Found: m/z 251.8001[M+].
	With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 - 60℃; for 1.66667h;Inert atmosphere;	A dry nitrogen-flushed 5 L 4-neck round bottom flask is charged with 100 g (Purity: 98%, 0.389 mol 1.0 eq.) of 3-(2-chloro-4-(cyclopentylamino)pyrimidin-5-yl)prop-2-yn-1-01, (A1d), 880 g (1000 mL) of peroxide free tetrahydrofuran and 753 g, (856 mL) of tetrabutylammonium fluoride, 1.0M solution in THF. The content is stirred at 25 C. for 10 min, and then the solution is warmed to 60 C. This temperature is maintained for 1.5 h until the starting material, A1d, is ?2.5±0.5% as determined by HPLC analysis. The resulting solution is cooled to below 30±3 C. , and distilled under reduced pressure to remove THF. 79 g (100 mL) of 2-propanol is added. The sample is stirred for 15 min and 1000 g (1000 mL) of water then add slowly over 30 min The sample is stirred at 20±3 C. for 30 min and then filtered. The cake is washed twice with 200 g (2*100 mL) of water. The solids are dried at 50 C. for 16 h to afford Compound A1c as a tan, crystalline solid, mp=174-176 C.

20.2 g

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 - 60℃; for 4.16667h;

To a solution of 3-(2-chloro-4-(cyclopentylamino)pyrimidin-5-yl)prop-2-yn-l-ol (27 g) in tetrahydrofuran (270 mL) was added a solution of tetra butyl ammonium fluoride in tetrahydrofuran (1M , 268 mL) at 25-30 C and stirred for 10 minutes at the same temperature. The reaction mass was then heated to 60 C and stirred for 4 hours at the same temperature. The reaction mass was then cooled to 25-30 C and evaporated under reduced pressure at 45 C. Residue obtained from the evaporation was dissolved in 2-propanol (270 mL) and stirred for 15 minutes at 25-30 C. Water (270 mL) was added to the above solution and again stirred for 30 minutes at 20 C. Resulting solid compound was then filtered, washed with water (2 x 30 mL) followed by n- hexane (100 mL) and methyl tert-butyl ether (100 mL), dried for 16 hours at 50 C to afford the title compound. (0160) Yield: 20 2 g; Purity by HPLC: 95 25 %

Reference： [1]Patent: EP3434676,2019,A1 .Location in patent: Paragraph 0109; 0112; 0113
[2]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712
[3]Patent: US2012/115878,2012,A1 .Location in patent: Page/Page column 7
[4]Patent: WO2018/51280,2018,A1 .Location in patent: Page/Page column 20

5
[ 1374639-77-6 ]
[ 1211441-98-3 ]

Reference： [1]Patent: US2012/115878,2012,A1
[2]Patent: WO2018/51280,2018,A1

6
[ 1374639-77-6 ]
[ 1374639-78-7 ]

Reference： [1]Patent: US2012/115878,2012,A1
[2]Patent: WO2018/51280,2018,A1

7
[ 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

8
[ 1374639-77-6 ]
(E)-3-(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-1-(thiophene-2-yl)-prop-2-en-1-one [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

9
[ 1374639-77-6 ]
(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethylene)phenylamine [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

10
[ 1374639-77-6 ]
(4-bromo-phenyl)-(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethylene)amine [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

11
[ 1374639-77-6 ]
(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethylene)-(4-chloro-phenyl)amine [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

12
[ 1374639-77-6 ]
(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl)phenylamine [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

13
[ 1374639-77-6 ]
(4-bromo-phenyl)-(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl)amine [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

14
[ 1374639-77-6 ]
(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-ylmethyl)-(4-chlorophenyl)amine [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

15
[ 1374639-77-6 ]
[ 1211443-55-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	With manganese(IV) oxide; In tetrahydrofuran; at 10 - 29℃; for 2h;Inert atmosphere;	A solution of compound(4) (4 g, 15.9 mmol) in THF (60 mL) was stirred at 10-15 Cunder nitrogen atmosphere, manganese(IV)oxide (2.8 g, 31.7mmol) was added to the mixture and stirring was continuedfor 2 hours at 29 C. Progress of the reaction was monitoredby TLC. After completion of the reaction, the resultingmixture was filtered through celite bed and concentratedunder vacuum. The crude product was purified by columnchromatography using 2% of ethyl acetate and hexane aseluent to obtain compound (5). White crystalline solid,Yield: 72%, 152-154 C. 1H NMR (400 MHz, DMSO-d6):1.65-1.68 (m, 2H, -CH2), 1.99-2.03 (m, 4H, CH2), 2.14-2.16(m, 2H, CH2), 5.60-5.68 (m, 1H, -NH-CH-), 7.72 (s, 1H, Ar-H), 9.92 (s, 1H, Ar-H), 9.98 (s, 1H, CHO). 13C NMR (75.46MHz, DMSO-d6): 184.6, 156.6, 153.5, 137.5, 130.1, 116.9,56.3, 31.03, 24.9. ESI-HRMS (m/z): Calcd. ForC12H12ClN3O:249.6969. Found: m/z 249.0971 [M+].

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

16
[ 1374639-77-6 ]
(E)-3-(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-1-(5-methylfuran-2-yl)prop-2-en-1-one [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

17
[ 1374639-77-6 ]
(E)-3-(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-1-(5-methylthiophen-2-yl)prop-2-en-1-one [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

18
[ 1374639-77-6 ]
(E)-3-(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-1-(2,5-dimethyl-furan-3-yl)prop-2-en-1-one [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

19
[ 1374639-77-6 ]
(E)-3-(2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-1-(2,5-dimethylthiophene-3-yl)prop-2-en-1-one [ No CAS ]

Reference： [1]Combinatorial Chemistry and High Throughput Screening,2017,vol. 20,p. 703 - 712

20
[ 1374639-77-6 ]
ribociclib isethionic acid salt [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

21
[ 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 hydrochloride oxalate [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

22
[ 1374639-77-6 ]
ribociclib tartaric acid salt [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

23
[ 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 hydrochloride phosphate [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

24
[ 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 acetate [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

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[ 1374639-77-6 ]
ribociclib hydrobromic acid salt [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

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[ 1374639-77-6 ]
ribociclib trifluoroacetic acid salt [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

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[ 1374639-77-6 ]
ribociclib citric acid salt [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

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[ 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 hydrochloride sulfate [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

29
[ 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 hydrochloride tosylate [ No CAS ]

Reference： [1]Patent: WO2018/51280,2018,A1

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[ 571188-59-5 ]
[ 1374639-77-6 ]
tert-butyl 4-(6-((7-cyclopentyl-6-(hydroxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)pyridin-3-yl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5.2 g	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; at 25 - 100℃; for 3h;	To a mixture of <strong>[1374639-77-6](2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methanol</strong> (IVa) (4.5 g) and tert-butyl 4-(6-aminopyridin-3-yl)piperazine-l-carboxylate (Va) (4.97 g) in methyl isobutyl ketone (36 mL) was added palladium (II) acetate (0.08 g) and 2,2'- bis(diphenylphosphino)-l, l'-binaphthyl (0.44 g) at 25-30 C. The reaction mass was then heated to 40 C. Cesium carbonate (8.73 g) was added to the above reaction mass portion wise at 40 C. The reaction mass was heated to 100 C and stirred for 3 hours. The reaction mass was cooled to 70 C. Water (36 mL) was added to the above reaction mass at 70 C and again cooled to 50 C. n-Heptane (54 mL) was added to the above reaction mass drop wise at 50 C. The reaction mass was again cooled to 20 C and stirred for 2 hours at the same temperature. Resulting solid compound was then filtered, washed with ^-Heptane (2 chi 10 mL) and dried for 4 hours at 50 C to afford title compound. (0163) Yield: 5 2 g; Purity by HPLC: 97 01 %

Reference： [1]Patent: WO2018/51280,2018,A1 .Location in patent: Page/Page column 20

31
[ 1211443-58-1 ]
[ 1374639-77-6 ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

32
methyl 2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate [ No CAS ]
[ 1374639-77-6 ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

33
[ 1374639-77-6 ]
3-(1-((2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methyl)-1H-1,2,3-triazol-4-yl)aniline [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

34
[ 1374639-77-6 ]
2-chloro-7-cyclopentyl-6-((4-(phenanthren-9-yl)-1H-1,2,3-triazol-1-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

35
[ 1374639-77-6 ]
2-chloro-7-cyclopentyl-6-((4-(3,4-dichlorophenyl)-1H-1,2,3-triazol-1-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

36
[ 1374639-77-6 ]
6-((4-([1,1′-biphenyl]-4-yl)-1H-1,2,3-triazol-1-yl)methyl)-2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

37
[ 1374639-77-6 ]
2-chloro-7-cyclopentyl-6-((4-(4-methoxy-2-methylphenyl)-1H-1,2,3-triazol-1-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

38
[ 1374639-77-6 ]
1-(1-((2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methyl)-1H-1,2,3-triazol-4-yl)hexan-1-ol [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

39
[ 1374639-77-6 ]
2-chloro-7-cyclopentyl-6-((4-(p-tolyl)-1H-1,2,3-triazol-1-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

40
[ 1374639-77-6 ]
2-chloro-6-((4-(3-chloropropyl)-1H-1,2,3-triazol-1-yl)methyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

41
[ 1374639-77-6 ]
2-chloro-7-cyclopentyl-6-((4-heptyl-1H-1,2,3-triazol-1-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

42
[ 1374639-77-6 ]
2-chloro-7-cyclopentyl-6-((4-hexyl-1H-1,2,3-triazol-1-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

43
[ 1374639-77-6 ]
2-chloro-7-cyclopentyl-6-((4-pentyl-1H-1,2,3-triazol-1-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

44
[ 1374639-77-6 ]
(1-((2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)methyl)-1H-1,2,3-triazol-4-yl)methanol [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

45
[ 1374639-77-6 ]
2-chloro-7-cyclopentyl-6-((4-(imidazo[1,2-b]pyridazin-3-yl)-1H-1,2,3-triazol-1-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

46
[ 1374639-77-6 ]
6-(azidomethyl)-2-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

47
[ 1374639-77-6 ]
[ 124-63-0 ]
C₁₃H₁₆ClN₃O₃S [ No CAS ]

Reference： [1]Toxicology in Vitro,2019,vol. 60,p. 87 - 96

48
[ 1374639-77-6 ]
2-((5-acrylamido-4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methoxyphenyl)amino)-N-(3-cyanophenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C 2.1: potassium peroxomonosulfate / N,N-dimethyl-formamide / 20 °C 3.1: N-ethyl-N,N-diisopropylamine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; benzotriazol-1-ol / dichloromethane / 0.33 h 3.2: 6 h / 20 °C 4.1: palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; Cs₂CO₃ / 1,4-dioxane / 10 h / 100 °C / Inert atmosphere