[ CAS No. 3680-69-1 ] {[proInfo.proName]}

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2D 3D

Structure of 3680-69-1 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 3680-69-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3680-69-1 ]

SDS Specification

Alternatived Products of [ 3680-69-1 ]

Product Citations

Synthesis and biological evaluation of selected 7H-pyrrolo[2,3-d]pyrimidine derivatives as novel CDK9/CyclinT and Haspin inhibitors

Pieterse, Lianie ; Beteck, Richard M. ; Baratte, Blandine , et al. Chem.-Biol. Interac.,2021,349,109643. DOI: 10.1016/j.cbi.2021.109643 PubMed ID: 34508710

Abstract: Protein kinases, including CDK9/CyclinT and Haspin, are regarded as potential drug targets in cancer therapy. Findings from a previous study suggested 7-azaindole as a privileged scaffold for producing inhibitors of CDK9/CyclinT and Haspin. Inspired by these findings, the current study synthesized and evaluated thirteen (13) C6-substituted 7-azaindole and twenty (20) C4-substituted structurally related 7H-pyrrolo[2,3-d]pyrimidine derivatives against a panel of protein kinases, including CDK9/CyclinT and Haspin. Eleven of the 7H-pyrrolo[2,3-d]pyrimidine derivatives exhibited activity toward CDK9/CyclinT, while 4 of compounds had activity against Haspin. The best CDK9/CyclinT (IC50 of 0.38 μM) and Haspin (IC50 of 0.11 μM) activities were achieved by compounds 7d and 7f, resp. Hence, these compounds may be valuable starting points for development of new anti-cancer drugs.

Keywords: 7-Deazapurine ; Anticancer ; CDK9/CylinT ; Haspin ; Protein kinase

Purchased from AmBeed: 98437-24-2 ; 71597-85-8 ; 3680-69-1 ; 6165-68-0 ; 51067-38-0 ; 87199-18-6

Product Details of [ 3680-69-1 ]

CAS No. :	3680-69-1	MDL No. :	MFCD01686865
Formula :	C₆H₄ClN₃	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	BPTCCCTWWAUJRK-UHFFFAOYSA-N
M.W :	153.57	Pubchem ID :	5356682
Synonyms :		Chemical Name :	4-Chloro-7H-pyrrolo[2,3-d]pyrimidine

Calculated chemistry of [ 3680-69-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	38.9
TPSA :	41.57 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.43
Log Po/w (XLOGP3) :	1.62
Log Po/w (WLOGP) :	1.61
Log Po/w (MLOGP) :	0.78
Log Po/w (SILICOS-IT) :	2.24
Consensus Log Po/w :	1.54

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.51 mg/ml ; 0.00332 mol/l
Class :	Soluble
Log S (Ali) :	-2.11
Solubility :	1.21 mg/ml ; 0.00785 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.14
Solubility :	0.112 mg/ml ; 0.000728 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.27

Safety of [ 3680-69-1 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3680-69-1 ]

* 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 [ 3680-69-1 ]
Downstream synthetic route of [ 3680-69-1 ]

[ 3680-69-1 ] Synthesis Path-Upstream 1~3

1
[ 100-44-7 ]
[ 3680-69-1 ]
[ 16019-34-4 ]

Reference： [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 19, p. 3884 - 3888
[2] Patent: US2002/19526, 2002, A1,

2
[ 100-39-0 ]
[ 3680-69-1 ]
[ 16019-34-4 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 18, p. 5473 - 5482

3
[ 3680-69-1 ]
[ 16019-34-4 ]

Reference： [1] Tetrahedron Letters, 1998, vol. 39, # 32, p. 5685 - 5688

[ 3680-69-1 ] Synthesis Path-Downstream 1~4

1
[ 52133-67-2 ]
[ 3680-69-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5247 - 5250
[2]European Journal of Organic Chemistry,1998,p. 827 - 835
[3]Russian Journal of Bioorganic Chemistry,1995,vol. 21,p. 756 - 761
Bioorganicheskaya Khimiya,1995,vol. 21,p. 874 - 880
[4]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4064 - 4067
[5]Patent: CN107033206,2017,A
[6]Archiv der Pharmazie,2018,vol. 351
[7]Patent: WO2007/125315,2007,A2
[8]Patent: CN108794479,2018,A

2
[ 32202-61-2 ]
[ 3680-69-1 ]
N-(2,3-dihydro-1H-inden-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
5%		To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.075 g, 0.488 mmol) and <strong>[32202-61-2]4-aminoindan</strong> (0.072 g, 0.537mmol) in isopropanol (1 ml) was added concentrated HCl (2 drops). The reaction was heated at 600C for 5 h, then cooled to room temperature and concentrated to dryness. The reaction was diluted with ethyl acetate (5 ml) and washed with saturated aqueous NaHCO3 solution (3 x 5 ml). The organic extract was washed with H2O (5 ml), washed with brine (5 ml), dried (Na2SO4), and concentrated. The crude material was purified by column chromatography on silica gel (0-5 percent DCM/MeOH). The resulting material was recrystallized from ethyl acetate/hexanes to give the desired product (0.0060 g, 5percent) as a white solid.1H NMR (300 MHz, CD3OD) delta ppm: 2.06 (t, J = 7 Hz, 2 H), 2.82 (t, J = 7 Hz, 2 H), 2.99 (t, J = 7 Hz, 2 H), 6.29 (d, J = 4 Hz, 1 H), 7.09 (d, J = 4 Hz, 1 H), 7.16 - 7.23 (m, 3 H), 8.10 (s, 1 H). HPLC: 100percent at 2.100 minutes; Sunfire C18 4.6 x 50 mm; 10-90percent methanol: water with 0.1percent TFA; Gradient time = 2 min; 3.5 ml/ min; 254 nm. MS = 251 M+H+.
5%		To a stirred solution of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (0.075 g, 0.488 mmol) and <strong>[32202-61-2]4-aminoindan</strong> (0.072 g, 0.537mmol) in isopropanol (1 ml) was added concentrated HCl (2 drops). The reaction was heated at 600C for 5 h, then cooled to room temperature and concentrated to dryness. The reaction was diluted with ethyl acetate (5 ml) and washed with saturated aqueous NaHCO3 solution (3 x 5 ml). The organic extract was washed with H2O (5 ml), washed with brine (5 ml), dried (Na2SO4), and concentrated. The crude material was purified by column chromatography on silica gel (0-5 percent DCM/MeOH). The resulting material was recrystallized from ethyl acetate/hexanes to give the desired product (0.0060 g, 5percent) as a white solid.1H NMR (300 MHz, CD3OD) delta ppm: 2.06 (t, J = 7 Hz, 2 H), 2.82 (t, J = 7 Hz, 2 H), 2.99 (t, J = 7 Hz, 2 H), 6.29 (d, J = 4 Hz, 1 H), 7.09 (d, J = 4 Hz, 1 H), 7.16 - 7.23 (m, 3 H), 8.10 (s, 1 H). HPLC: 100percent at 2.100 minutes; Sunfire C18 4.6 x 50 mm; 10-90percent methanol: water with 0.1percent TFA; Gradient time = 2 min; 3.5 ml/ min; 254 nm. MS = 251 M+H+.

Reference： [1]Patent: WO2008/89307,2008,A2 .Location in patent: Page/Page column 38
[2]Patent: WO2008/89310,2008,A2 .Location in patent: Page/Page column 41

3
[ 3680-69-1 ]
[ 876343-10-1 ]

Reference： [1]European Journal of Pharmaceutical Sciences,2014,vol. 59,p. 69 - 82
[2]Patent: WO2015/959,2015,A1

4
[ 1175298-09-5 ]
[ 3680-69-1 ]
tert-butyl (3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; water; at 100℃; for 14h;Inert atmosphere;	To 4-chloro-7H-pyrrolo[2,3-d]pyrimidin (2.97 g), the compound (9.39 g) of Reference Example 1(2a) and tripotassiumphosphate (10.2 g), 1,4-dioxane (66 mL) and water (11 mL) were added, followed by nitrogen substitution, andPdCl2(dppf)CH2Cl2 (1.41 g) was then added to the reaction mixture. The thus obtained mixture was stirred at 100C for14 hours. Thereafter, the reaction mixture was cooled to a room temperature, and ethyl acetate and water were thenadded to the mixture. Thereafter, the thus obtained mixture was filtered through Celite. The filtrate was then extractedwith ethyl acetate, and the gathered organic layer was then washed with water and then with a saturated saline. Theresultant was dried over anhydrous sodium sulfate, and was then concentrated under a reduced pressure. The obtainedresidue was purified by silica gel chromatography (chloroform : methanol) to obtain tert-butyl (3-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)cyclohex-3-en-1-yl)carbamate. The above obtained compound was used in the subsequent reaction withoutfurther purification.

Reference： [1]Patent: EP3330271,2018,A1 .Location in patent: Paragraph 0122; 0123

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

Pharmaceutical Intermediates of
[ 3680-69-1 ]

Ruxolitinib Related Intermediates

[ 1146629-77-7 ]

(4-(1H-Pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl pivalate

[ 269410-08-4 ]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

[ 591769-05-0 ]

3-Cyclopentylacrylonitrile

[ 73183-34-3 ]

4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi(1,3,2-dioxaborolane)

[ 2075-45-8 ]

4-Bromo-1H-pyrazole

Baricitinib Related Intermediates

[ 91-00-9 ]

Diphenylmethanamine

[ 398489-26-4 ]

tert-Butyl 3-oxoazetidine-1-carboxylate

[ 1029716-44-6 ]

1-(1-Ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

[ 941685-26-3 ]

4-Chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidine

[ 141699-55-0 ]

tert-Butyl 3-hydroxyazetidine-1-carboxylate

Related Functional Groups of
[ 3680-69-1 ]

Chlorides

[ 7781-10-4 ]

4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.96

[ 84955-31-7 ]

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Similarity: 0.91

[ 90213-66-4 ]

2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.91

[ 16019-34-4 ]

7-Benzyl-4-chloro-7H-pyrrolo[2,3-d] pyrimidine

Similarity: 0.89

[ 90213-67-5 ]

2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.87

Related Parent Nucleus of
[ 3680-69-1 ]

Other Aromatic Heterocycles

[ 7781-10-4 ]

4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.96

[ 84955-31-7 ]

4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Similarity: 0.91

[ 90213-66-4 ]

2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.91

[ 16019-34-4 ]

7-Benzyl-4-chloro-7H-pyrrolo[2,3-d] pyrimidine

Similarity: 0.89

[ 90213-67-5 ]

2,4-Dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

Similarity: 0.87

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[ CAS No. 3680-69-1 ] {[proInfo.proName]}

Quality Control of [ 3680-69-1 ]

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Product Details of [ 3680-69-1 ]

Calculated chemistry of [ 3680-69-1 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 3680-69-1 ]

Application In Synthesis of [ 3680-69-1 ]

[ 3680-69-1 ] Synthesis Path-Upstream 1~3

[ 3680-69-1 ] Synthesis Path-Downstream 1~4

Technical Information

Pharmaceutical Intermediates of [ 3680-69-1 ]

Ruxolitinib Related Intermediates

Baricitinib Related Intermediates

Related Functional Groups of [ 3680-69-1 ]

Chlorides

Related Parent Nucleus of [ 3680-69-1 ]

Other Aromatic Heterocycles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Pharmaceutical Intermediates of
[ 3680-69-1 ]

Related Functional Groups of
[ 3680-69-1 ]

Related Parent Nucleus of
[ 3680-69-1 ]