[ CAS No. 1156390-49-6 ]

Name: 1156390-49-6|6-Chloro-2-oxoindoline-5-carboxylic acid|97%
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Quality Control of [ 1156390-49-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1156390-49-6 ]

Product Details of [ 1156390-49-6 ]

CAS No. :	1156390-49-6	MDL No. :	MFCD12174764
Formula :	C₉H₆ClNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GALGGHJFGWMWCN-UHFFFAOYSA-N
M.W :	211.60 g/mol	Pubchem ID :	43457499
Synonyms :

Calculated chemistry of [ 1156390-49-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.11
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	53.7
TPSA :	66.4 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.97
Log Po/w (XLOGP3) :	0.93
Log Po/w (WLOGP) :	0.96
Log Po/w (MLOGP) :	1.29
Log Po/w (SILICOS-IT) :	1.83
Consensus Log Po/w :	1.2

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.99
Solubility :	2.17 mg/ml ; 0.0103 mol/l
Class :	Very soluble
Log S (Ali) :	-1.91
Solubility :	2.6 mg/ml ; 0.0123 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.88
Solubility :	0.276 mg/ml ; 0.0013 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.69

Safety of [ 1156390-49-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H317	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1156390-49-6 ]

* 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 [ 1156390-49-6 ]
Downstream synthetic route of [ 1156390-49-6 ]

[ 1156390-49-6 ] Synthesis Path-Upstream 1~2

1
[ 118307-04-3 ]
[ 1156390-49-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 13, p. 3500 - 3511

2
[ 56341-37-8 ]
[ 1156390-49-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 13, p. 3500 - 3511

[ 1156390-49-6 ] Synthesis Path-Downstream 1~11

1
[ 1156390-49-6 ]
[ 51639-48-6 ]
[ 1374752-87-0 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃;	A solution of l-(4-(piperazin-l-yl)phenyl)ethanone (86.0 mg, 0.420 mmol; available from Aldrich), 6- chloro-2-oxoindoline-5-carboxylic acid (74.1 mg, 0.350 mmol; available from Ryan Scientific) in DMF (2.00 mL) will be treated at room temperature with EDC (67.0 mg, 0.350 mmol) and DMAP (43.0 mg, 0.350 mmol). The reaction mixture will be stirred at room temperature for overnight. The crude mixture will be filtered through a frit and purified by preparative HPLC to give the final product.

Reference： [1]Patent: WO2012/61597,2012,A1 .Location in patent: Page/Page column 37; 38

2
[ 1156390-49-6 ]
N-[(1R,3r,5S)-8-(4-aminopiperidine-1-sulfonyl)-8-azabicyclo[3.2.1]octan-3-yl]-6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxamide hydrochloride [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 134 - 138
[2]Patent: KR2017/45749,2017,A

3
[ 1156390-49-6 ]
N-[(1R,3r,5S)-8-[4-(benzylamino)piperidine-1-sulfonyl]-8-azabicyclo[3.2.1]octan-3-yl]-6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxamide trifluoroacetate [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 134 - 138

4
[ 1156390-49-6 ]
tert-butyl N-[1-[(1R,3r,5S)-3-amino-8-azabicyclo[3.2.1]octane-8-sulfonyl]piperidin-4-yl]carbamate [ No CAS ]
tert-butyl N-[1-[(1R,3r,5S)-3-(6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxamido)-8-azabicyclo[3.2.1]octane-8-sulfonyl]piperidin-4-yl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 0 - 20℃; for 2h;	Into a 25-mL round-bottom flask was placed 6-chloro-2-oxo-2,3-dihydro-1H- indole-5-carboxylic acid (170 mg, 0.80 mmol, 1.00 equiv), dichloromethane (10 mL), HOBT (216 mg, 1.60 mmol, 2.00 equiv), EDCI (306 mg, 1.60 mmol, 2.00 equiv), and tert-butyl N-1-[(1R,3r,5S)-3-amino-8-azabicyclo[3.2.1]octane-8-sulfonyl]piperidin-4- ylcarbamate (375 mg, 0.97 mmol, 1.20 equiv). This was followed by the addition of TEA (400 mg, 3.95 mmol, 5.00 equiv) dropwise with stirring at 0oC. The resulting solution was stirred for 2 h at room temperature. The reaction mixture was diluted with 10 mL of dichloromethane and washed with 2x5 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was chromatographed on a silica gel column with ethyl acetate/petroleum ether (3:1). This resulted in 300 mg (64%) of tert-butyl N-[1-[(1R,3r,5S)-3-(6-chloro-2-oxo-2,3-dihydro- 1H-indole-5-carboxamido)-8-azabicyclo[3.2.1]octane -8- sulfonyl] piperidin-4- yl]carbamate as a red solid

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 134 - 138
[2]Patent: KR2017/45749,2017,A .Location in patent: Paragraph 0790; 0793-0795

5
[ 1156390-49-6 ]
(1R,3S,5S)-8-([[1-(4,4,4-trifluorobutyl)piperidin-4-yl]methane]sulfonyl)-8-azabicyclo[3.2.1]octan-3-amine [ No CAS ]
6-chloro-2-oxo-N-[(1R,3S,5S)-8-([[1-(4,4,4-trifluorobutyl)piperidin-4-yl]methane]sulfonyl)-8-azabicyclo[3.2.1]octan-3-yl]-2,3-dihydro-1H-indole-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 10℃; for 12h;	Into a 100-mL round-bottom flask, was placed N,N-dimethylformamide (10 mL), (1R,3S,5S)-8-([[1-(4,4,4-trifluorobutyl)piperidin-4-yl]methane]sulfonyl)-8- azabicyclo[3.2.1]octan-3-amine (50 mg, 0.13 mmol, 1.00 equiv), 6-chloro-2-oxo-2,3- dihydro-1H-indole-5-carboxylic acid (46 mg, 0.22 mmol, 1.73 equiv), 1H-1,2,3- benzotriazol-1-ol (35 mg, 0.26 mmol, 2.06 equiv), EDCI (50 mg, 0.26 mmol, 2.07 equiv), TEA (0.3 mL). The resulting solution was stirred for 12 h at 10oC. The solids were filtered out. The resulting mixture was diluted with 10 mL of water. The resulting solution was extracted with of 2x10 mL dichloromethane and the organic layers combined. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude reside was purified by Prep-HPLC with the following conditions (2-Waters 2767-2(HPLC-08)): Column, Xbridge Prep Phenyl, 5 um, 19x150 mm; mobile phase, Water with 50 mmol ammonium bicarbonate and acetonitrile (10.0% acetonitrile up to 33.0% in 2 min, up to 53.0% in 8 min, up to 100.0% in 1 min, down to 10.0% in 1 min); Detector, UV 254 nm. This resulted in 5.7 mg (8%) of 6-chloro-2-oxo- N-[(1R,3S,5S)-8-([[1-(4,4,4-trifluorobutyl)piperidin-4-yl]methane]sulfonyl)-8- azabicyclo[3.2.1]octan-3-yl]-2,3-dihydro-1H-indole-5-carboxamide as a light pink solid

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 134 - 138
[2]Patent: KR2017/45749,2017,A .Location in patent: Paragraph 0802; 0803; 0823-0825

6
[ 56341-37-8 ]
[ 1156390-49-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3500 - 3511

7
[ 118307-04-3 ]
[ 1156390-49-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3500 - 3511

8
[ 1156390-49-6 ]
(3Z)-6-chloro-N-[(1S)-2-hydroxy-1-phenylethyl]-3-(1H-pyrrol-2-ylmethylidene)-2-oxoindole-5-carboxamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3500 - 3511

9
[ 1156390-49-6 ]
[ 20989-17-7 ]
C₁₇H₁₅ClN₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3500 - 3511

10
[ 1156390-49-6 ]
N-[(1R,3r,5S)-8-[4-(benzylamino)piperidine-1-sulfonyl]-8-azabicyclo[3.2.1]octan-3-yl]-6-chloro-2-oxo-2,3-dihydro-1H-indole-5-carboxamide trifluoroacetate [ No CAS ]

Reference： [1]Patent: KR2017/45749,2017,A

11
[ 1156390-49-6 ]
tert-butyl ((2S)-1-(4-(1-aminoethyl)piperidin-1-yl)-1-oxopropan-2-yl)carbamate [ No CAS ]
tert-butyl ((2S)-1-(4-(1-(6-chloro-2-oxoindoline-5-carboxamido)ethyl)piperidin-1-yl)-1-oxopropan-2-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20℃; for 3h;	To a mixture of <strong>[1156390-49-6]6-chloro-2-oxoindoline-5-carboxylic acid</strong> (100.00 mg, 472.59 umol, 1.00 Eq), HATU (179.69 mg, 472.59 umol, 1.00 Eq) and TEA (47.82 mg, 472.59 umol, 1.00 Eq) in DCM (10 mL) was added tert-butyl ((2S)-1-(4-(1- aminoethyl)piperidin-1-yl)-1-oxopropan-2-yl)carbamate (141.50 mg, 472.59 umol, 1.00 Eq).The mixture was stirred at 20oC for 3 hours. LCMS showed the reaction was complete. Water (5 mL) was added to the reaction and the aqueous phase was extracted with DCM (10 mL x 3). The combined organic phase was dried over anhydrous Na2SO4, filtered and concentrated in vacuum to afford tert-butyl ((2S)-1-(4-(1-(6-chloro-2- oxoindoline-5-carboxamido)ethyl)piperidin-1-yl)-1-oxopropan-2-yl)carbamate (100.00 mg, crude)

Reference： [1]Patent: KR2017/45749,2017,A .Location in patent: Paragraph 0646; 0649-0651

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[ CAS No. 1156390-49-6 ]

Quality Control of [ 1156390-49-6 ]

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[ 1156390-49-6 ] Synthesis Path-Upstream 1~2

[ 1156390-49-6 ] Synthesis Path-Downstream 1~11

Related Parent Nucleus of [ 1156390-49-6 ]

Indolines

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