[ CAS No. 117890-55-8 ] {[proInfo.proName]}

Name: 117890-55-8|2-Chloro-6,7-dihydro-5H-cyclopenta[b]pyridine|95%
Brand: Ambeed
SKU: A139767
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Quality Control of [ 117890-55-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 117890-55-8 ]

CAS No. :	117890-55-8	MDL No. :	MFCD09034995
Formula :	C₈H₈ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PBMLTRUXYZHCFT-UHFFFAOYSA-N
M.W :	153.61	Pubchem ID :	15012906
Synonyms :

Calculated chemistry of [ 117890-55-8 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.38
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.87
TPSA :	12.89 Å²

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) :	-5.46 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	2.5
Log Po/w (WLOGP) :	2.22
Log Po/w (MLOGP) :	2.06
Log Po/w (SILICOS-IT) :	3.25
Consensus Log Po/w :	2.42

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.81
Solubility :	0.237 mg/ml ; 0.00154 mol/l
Class :	Soluble
Log S (Ali) :	-2.42
Solubility :	0.589 mg/ml ; 0.00384 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.45
Solubility :	0.054 mg/ml ; 0.000352 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 117890-55-8 ]

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 [ 117890-55-8 ]

* 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 [ 117890-55-8 ]
Downstream synthetic route of [ 117890-55-8 ]

[ 117890-55-8 ] Synthesis Path-Upstream 1~9

1
[ 115122-63-9 ]
[ 117890-55-8 ]

Yield	Reaction Conditions	Operation in experiment
14 kg	With hydrogenchloride In waterReflux; Large scale	In the reaction kettle, 20 kg of the first intermediate was charged.20percent hydrochloric acid 200kg, reflux reaction,After the reaction, 2250 kg of hydrochloric acid was concentrated, discharged, and naturally crystallized.For the dip, there is no hydrogen chloride 2kg gas discharged from the organization, and 14kg of the second intermediate is obtained.

Reference： [1] Patent: CN108395402, 2018, A, . Location in patent: Paragraph 0004; 0006

2
[ 88499-85-8 ]
[ 117890-55-8 ]

Reference： [1] Journal of the American Chemical Society, 1931, vol. 53, p. 3160,3162

3
[ 1092444-79-5 ]
[ 117890-55-8 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 14, p. 3895 - 3898

4
[ 88499-85-8 ]
[ 117890-55-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 266 - 271
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1506 - 1509[3] Angew. Chem., 2017, vol. 129, # 6, p. 1528 - 1531,4

5
[ 856152-69-7 ]
[ 117890-55-8 ]

Reference： [1] Journal of the American Chemical Society, 1931, vol. 53, p. 3160,3162

6
[ 930-91-6 ]
[ 117890-55-8 ]

Reference： [1] Journal of the American Chemical Society, 1931, vol. 53, p. 3160,3162

7
[ 120-92-3 ]
[ 117890-55-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1506 - 1509[2] Angew. Chem., 2017, vol. 129, # 6, p. 1528 - 1531,4
[3] Patent: CN108395402, 2018, A,

8
[ 1192-54-7 ]
[ 117890-55-8 ]

Reference： [1] Patent: CN108395402, 2018, A,

9
[ 4594-77-8 ]
[ 117890-55-8 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 6, p. 1506 - 1509[2] Angew. Chem., 2017, vol. 129, # 6, p. 1528 - 1531,4

[ 117890-55-8 ] Synthesis Path-Downstream 1~60

1
[ 88499-85-8 ]
[ 117890-55-8 ]

Yield	Reaction Conditions	Operation in experiment
43.7%	With N,N-dimethyl-formamide; trichlorophosphate; at 120℃; for 3h;Inert atmosphere;	A mixture of 6,7-dihydro-5H-cyclopenta[b]pyridin-2-ol (70 g, 518 mmol), POCl3 (200.0 ml, 2146 mmol) and DMF (10 mL) was stirred under nitrogen atmosphere at 120 C for 3 h. After cooling, the mixture was poured into ice water, basified with 8 M NaOH aqueous solution and extracted with AcOEt. The extract was washed with brine, dried over anhydrous Na2S04, and concentrated. The resulted crude compound was purified by flash column chromatography (100- 200 silica mesh, eluent was 10% EtOAc in pet ether) to obtained 2-chloro-6,7-dihydro-5H- cyclopenta[b]pyridine (35 g, 43.7% yield) as an off white solid. 1H NMR (400 MHz, CDCl3): d 7.44 (d, / = 7.6 Hz, 1H), 7.06 (d, J = 8.0 Hz, 1H), 3.01 (t, / = 7.2 Hz, 2H), 2.92 (t, / = 7.2 Hz, 2H), 2.18-2.10 (m, 2H). LCMS (ES) m/z 154.09 [M+H]+

Reference： [1]Patent: WO2019/149959,2019,A1 .Location in patent: Page/Page column 64-66
[2]Journal of the American Chemical Society,1931,vol. 53,p. 3160,3162

2
[ 117890-55-8 ]
[ 67-64-1 ]
[ 175228-32-7 ]

Reference： [1]Chemistry Letters,1994,p. 1857 - 1860
[2]Heterocycles,1996,vol. 42,p. 305 - 317

3
[ 117890-55-8 ]
[ 175410-59-0 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 3905 - 3920

4
[ 117890-55-8 ]
(7R,7R')-7,7'-di(1-tert-butyldimethylsiloxy-1-methylethyl)-6,6',7,7'-tetrahydro-5H,5H'-2,2'-bi-1,1'-pyrindine [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 3905 - 3920
[2]Heterocycles,1996,vol. 42,p. 305 - 317

5
[ 117890-55-8 ]
[ 175416-88-3 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 3905 - 3920
[2]Heterocycles,1996,vol. 42,p. 305 - 317

6
[ 117890-55-8 ]
[ 175410-61-4 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 3905 - 3920

7
[ 117890-55-8 ]
[ 175410-63-6 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 3905 - 3920

8
[ 117890-55-8 ]
[ 175521-57-0 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 3905 - 3920

9
[ 117890-55-8 ]
(R)-2-Chloro-7-(2-methyl-oxiranyl)-6,7-dihydro-5H-[1]pyrindine [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 3905 - 3920

10
[ 117890-55-8 ]
[ 175410-62-5 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 3905 - 3920

11
[ 117890-55-8 ]
[ 175410-72-7 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 3905 - 3920

12
[ 117890-55-8 ]
[ 175228-33-8 ]

Reference： [1]Heterocycles,1996,vol. 42,p. 305 - 317

13
[ 856152-69-7 ]
[ 117890-55-8 ]

Reference： [1]Journal of the American Chemical Society,1931,vol. 53,p. 3160,3162

14
[ 930-91-6 ]
[ 117890-55-8 ]

Reference： [1]Journal of the American Chemical Society,1931,vol. 53,p. 3160,3162

15
[ 117890-55-8 ]
[ 911405-87-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 12h;	A solution of m-CPBA (4.7 g, 23.5 mmol, 1.2 eq, 85%) in DCM (25 niL) was added dropwise to a stirring solution of <strong>[117890-55-8]2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine</strong> (CAS 117890-55-8) (3.0 g, 19.6 mmol, 1.0 eq) in DCM (50 mL) and the resulting solution was allowed to stir at rt for 12 h. The reaction mixture was quenched with a saturated aqueous solution of Na2S203 and the organic layer was separated. The aqueous phase was then extracted with DCM (3x30 mL), and the combined organic extracts were washed with aqueous NaHC03, brine, dried over anhydrous Na2S04 and concentrated in vacuo to afford crude product as pale yellow solid (2.9 g, Y: 88%), which was used directly in the next step without further purification. ESI-MS (M+H) +: 170.0. 1H NMR (400 MHz, CDC13) delta: 7.33 (d, J = 7.8 Hz, 1H), 7.11 (d, J = 8.0 Hz, 1H), 3.31 - 3.13 (m, 2H), 3.12 - 2.96 (m, 2H), 2.31 - 2.16 (m, 2H).
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃;	[0233] A solution of 70 percent 3-chlorobenzoperoxoic acid (1.41 g, 5.73 mmol) in CH2C12 (15 ml) was added dropwise to a stirring solution of <strong>[117890-55-8]2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine</strong> (800 mg, 5.21 mmol) in CH2C12 (8 ml) and the resulting solution was allowed to stir at room temperature for overnight. The reaction mixture was quenched with saturated NaHC03 solution and the CH2C12 layer was separated. The aqueous phase was then extracted with CH2C12 (3 x 50 mL). The organic layer was combined, washed with brine (20 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure, the residue was purified by prep-TLC (eluting with hexane/ethyl acetate 1 : 1) to afford <strong>[117890-55-8]2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine</strong> 1 -oxide as a solid. LC/MS = 170 [M+l].
		A solution of m-chloroperbenzoic acid 70% (520.9 mg, 2.113 mmol) in 5 mL of CH2CI2 was added drop wise to a stirring solution of <strong>[117890-55-8]2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine</strong> (295mg, 1.921 mmol) in 3 mL of CH2CI2 and the resulting solution was allowed to stir at room temperature overnight. The reaction mixture was quenched with a saturated aqueous solution of NaHCO3 and the CH2CI2 layer was separated. The aqueous phase was then extracted with CH2CI2 (3X), and the combined organic extracts were washed with brine and then dried over anhydrous Na2SO4. After removing solvent at reduced pressure, the residue was purified by preparative TLC (eluting with 70% EtOAc/Hexane) to afford the title compound (1-1 a).MS calculated = 169.91 , MS+1 observed =170.0

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 266 - 271
[2]Tetrahedron Asymmetry,2009,vol. 20,p. 1425 - 1432
[3]Patent: WO2016/11390,2016,A1 .Location in patent: Page/Page column 111
[4]Patent: WO2016/81290,2016,A1 .Location in patent: Paragraph 0233
[5]Patent: WO2006/103511,2006,A1 .Location in patent: Page/Page column 33

16
[ 88499-85-8 ]
[ 117890-55-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 266 - 271
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 1506 - 1509
Angew. Chem.,2017,vol. 129,p. 1528 - 1531,4

17
[ 117890-55-8 ]
2-((tert-butyldimethylsilyloxy)methyl)cyclopropylboronic acid [ No CAS ]
2-(2-((tert-butyldimethylsilyloxy)methyl)cyclopropyl)-6,7-dihydro-5H-cyclopenta[b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With palladium diacetate; caesium carbonate; catacxium A; In water; at 100℃;	To a stirred solution of S-4 (3.0 g, 13.0 mol) in toluene (50 mL) was added 2- chloro-6,7-dihydro-5H-cyclopenta[b]pyridine (2.0 g, 13.0 mmol), palladium acetate (0.29 g, 1.30 mmol), di(l-adamantyl)-n-butylphosphine (1.40 g, 3.91 mmol), cesium carbonate (12.74 g, 39.10 mmol) and water (16.6 mL). The resulting mixture was heated to 100C overnight. The reaction was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic phase was concentrated and flash column separation using a 0-10% ethyl acetate/ hexane gradient gave S-5 as an oil. (3.19 g, 65%)

Reference： [1]Patent: WO2013/28590,2013,A1 .Location in patent: Page/Page column 50

18
[ 117890-55-8 ]
[ 1564274-58-3 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 140 - 146

19
[ 117890-55-8 ]
[ 1564274-60-7 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 140 - 146

20
[ 117890-55-8 ]
[ 1564274-62-9 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 140 - 146

21
[ 117890-55-8 ]
(S)-7-[(diphenylphosphanyl)methyl]-2-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridine borane adduct [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 140 - 146

22
[ 117890-55-8 ]
(S)-7-[(di-o-tolylphosphanyl)methyl]-2-phenyl-6,7-dihydro-5H-cyclopenta[b]pyridine borane adduct [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 140 - 146

23
[ 117890-55-8 ]
C₂₇H₂₄NP [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 140 - 146

24
[ 117890-55-8 ]
C₂₉H₂₈NP [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 140 - 146

25
[ 117890-55-8 ]
[ 616-38-6 ]
[ 1564274-76-5 ]
methyl (R)-2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 140 - 146

26
[ 117890-55-8 ]
[ 911405-88-4 ]

Reference： [1]Patent: WO2016/11390,2016,A1
[2]Patent: WO2016/81290,2016,A1
[3]Patent: WO2006/103511,2006,A1

27
[ 117890-55-8 ]
[ 911405-91-9 ]

Reference： [1]Patent: WO2016/81290,2016,A1
[2]Patent: WO2006/103511,2006,A1
[3]Patent: WO2016/11390,2016,A1

28
[ 117890-55-8 ]
[ 1150617-92-7 ]

Reference： [1]Patent: WO2016/81290,2016,A1
[2]Patent: WO2016/11390,2016,A1

29
[ 117890-55-8 ]
2-(1-(6-(trifluoromethyl)pyridin-2-yl)-1H-indazol-6-yl)-5H-cyclopenta[b]pyridin-7(6H)-one [ No CAS ]

Reference： [1]Patent: WO2016/11390,2016,A1

30
[ 117890-55-8 ]
2-(1-(6-(trifluoromethyl)pyridin-2-yl)-1H-indazol-6-yl)-5H-cyclopenta[b]pyridin-7(6H)-one oxime [ No CAS ]

Reference： [1]Patent: WO2016/11390,2016,A1

31
[ 117890-55-8 ]
2-(1-(6-(trifluoromethyl)pyridin-2-yl)-1H-indazol-6-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amine [ No CAS ]

Reference： [1]Patent: WO2016/11390,2016,A1

32
[ 117890-55-8 ]
2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amine [ No CAS ]

Reference： [1]Patent: WO2016/81290,2016,A1

33
[ 117890-55-8 ]
2-chloro-N-(2,4-dimethoxybenzyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amine [ No CAS ]

Reference： [1]Patent: WO2016/81290,2016,A1

34
[ 117890-55-8 ]
[ 78-83-1 ]
2-isobutoxy-6,7-dihydro-5H-cyclopenta[b]pyridine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1506 - 1509
Angew. Chem.,2017,vol. 129,p. 1528 - 1531,4

35
[ 120-92-3 ]
[ 117890-55-8 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1506 - 1509
Angew. Chem.,2017,vol. 129,p. 1528 - 1531,4
[2]Patent: CN108395402,2018,A

36
[ 4594-77-8 ]
[ 117890-55-8 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 1506 - 1509
Angew. Chem.,2017,vol. 129,p. 1528 - 1531,4

37
[ 1092444-79-5 ]
[ 117890-55-8 ]
3-chloro-6,7-dihydro-5H-cyclopenta[c]pyridine [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 3895 - 3898

38
[ 117890-55-8 ]
(S)-2-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-N-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxamide [ No CAS ]
(R)-2-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-N-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2017/205536,2017,A2

39
[ 117890-55-8 ]
2-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxylic acid [ No CAS ]

Reference： [1]Patent: WO2017/205536,2017,A2

40
[ 117890-55-8 ]
2-(7-(difluoromethyl)-6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinolin-1(2H)-yl)-N-methyl-6,7-dihydro-5H-cyclopenta[b]pyridine-7-carboxamide [ No CAS ]

Reference： [1]Patent: WO2017/205536,2017,A2

41
[ 117890-55-8 ]
[ 616-38-6 ]
[ 1190392-51-8 ]

Yield	Reaction Conditions	Operation in experiment
38%		To a solution of<strong>[117890-55-8]2-chloro-6,7-dihydro-5H-cyclopenta[b]pyridine</strong> (500 mg,3.26 mmol)indiethyl ether (30 mL)at -30 C was added LiHMDS (2M in THF,3.26 mL,6.51 mmol)dropwised under a nitrogen atmosphere. The mixture was stirred at -30 C for 1 hand dimethylcarbonate (0.30 mL,3.58 mmol)was added. After stirring at -30 C for 1 h,the mixture waswarmed to room temperature and stirred for an additional 12 h. The reaction mixture was15 quenched with sat. aq. NH4Cl (20 mL)and extracted with DCM (20 mL). The organic layer waswashed with water (20 mL x 2),brine (20 mL),dried over anhydrous Na2S04,filtered andconcentrated in vacuo. The crude residue was purified by silica gel column chromatography(EtOAc)to give the title compound (260 mg,38%)as colorless oil. LCMS M/Z (M+H)212

Reference： [1]Patent: WO2017/205536,2017,A2 .Location in patent: Page/Page column 187

42
[ 115122-63-9 ]
[ 117890-55-8 ]

Yield	Reaction Conditions	Operation in experiment
14 kg	With hydrogenchloride; In water;Reflux; Large scale;	In the reaction kettle, 20 kg of the first intermediate was charged.20% hydrochloric acid 200kg, reflux reaction,After the reaction, 2250 kg of hydrochloric acid was concentrated, discharged, and naturally crystallized.For the dip, there is no hydrogen chloride 2kg gas discharged from the organization, and 14kg of the second intermediate is obtained.

Reference： [1]Patent: CN108395402,2018,A .Location in patent: Paragraph 0004; 0006

43
[ 1192-54-7 ]
[ 117890-55-8 ]

Reference： [1]Patent: CN108395402,2018,A

44
[ 117890-55-8 ]
[ 533-37-9 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; In ethanol;Large scale;	35 kg of ethanol was put into the hydrogenation kettle.Catalyst 1,Put the second step intermediate 19kg with stirring.Controlling the temperature to react between certain temperatures,Until the hydrogen is no longer absorbed, after the hydrogenation is completed, the material is discharged.The catalyst was recovered and the ethanol was concentrated to dryness under reduced pressure.

Reference： [1]Patent: CN108395402,2018,A .Location in patent: Paragraph 0005; 0006

45
[ 117890-55-8 ]
[ 911405-90-8 ]
[ 911405-89-5 ]

Reference： [1]Patent: WO2006/103511,2006,A1

46
[ 117890-55-8 ]
[ 911405-92-0 ]

Reference： [1]Patent: WO2006/103511,2006,A1

47
[ 611-10-9 ]
[ 117890-55-8 ]