[ CAS No. 100122-02-9 ]

Name: 100122-02-9|4-Chloro-6,7-dimethoxy-2-methylquinoline|95%
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Quality Control of [ 100122-02-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 100122-02-9 ]

Product Details of [ 100122-02-9 ]

CAS No. :	100122-02-9	MDL No. :	MFCD11868302
Formula :	C₁₂H₁₂ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RBFMLSFDCICSHW-UHFFFAOYSA-N
M.W :	237.68	Pubchem ID :	39732475
Synonyms :

Calculated chemistry of [ 100122-02-9 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	64.7
TPSA :	31.35 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.82
Log Po/w (XLOGP3) :	3.16
Log Po/w (WLOGP) :	3.21
Log Po/w (MLOGP) :	1.99
Log Po/w (SILICOS-IT) :	3.54
Consensus Log Po/w :	2.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.63
Solubility :	0.0551 mg/ml ; 0.000232 mol/l
Class :	Soluble
Log S (Ali) :	-3.49
Solubility :	0.0771 mg/ml ; 0.000325 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.97
Solubility :	0.00257 mg/ml ; 0.0000108 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.83

Safety of [ 100122-02-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 100122-02-9 ]

* 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 [ 100122-02-9 ]

[ 100122-02-9 ] Synthesis Path-Downstream 1~12

1
[ 100122-02-9 ]
[ 105911-73-7 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium methylate

Reference： [1]Current Patent Assignee: BAYER AG - US2783234, 1952, A

2
[ 803630-29-7 ]
[ 100122-02-9 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate

Reference： [1]Current Patent Assignee: BAYER AG - US2783234, 1952, A

3
[ 72407-17-1 ]
[ 13061-96-6 ]
[ 100122-02-9 ]

Yield	Reaction Conditions	Operation in experiment
18%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 120℃;	To a solution of intermediate l-04c (4 g, 0.016 mol) in dioxane (60 ml_) was added methylboronic acid (R-04a) (1 .02 g, 0.017 mol), K2CO3 (4.3 g, 0.0312 mol), Pd(Ph3)4 (1 .8 g, 0.0016 mol), the solution was heated to 120 C overnight. The reaction mixture was concentrated and extracted with AcOEt. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product which was purified by column chromatography (eluent gradient PE:EA=1 :0 to 3:1 ) to give intermediate l-09a (0.7g, 18% yield) as a yellow solid. ESI-MS (M+1 ): 238 calc. for C12H12CINO2: 237.0.

Reference： [1]Patent: WO2020/141470,2020,A1 .Location in patent: Paragraph 001172; 001175
[2]Patent: WO2015/192981,2015,A1 .Location in patent: Page/Page column 56

4
[ 41838-46-4 ]
[ 100122-02-9 ]
[ 76-05-1 ]
6,7-dimethoxy-2-methyl-N-(1-methyl-4-piperidyl)quinolin-4-amine 2,2,2-trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.15%	Stage #1: 4-Amino-1-methylpiperidine; 4-chloro-6,7-dimethoxy-2-methylquinoline With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; CyJohnPhos In 1,2-dimethoxyethane at 110℃; for 3h; Microwave irradiation; Stage #2: trifluoroacetic acid In water; acetonitrile at 20℃;	Preparation of compound 3-01 : 6,7-dimethoxy-2-methyl-N-(1 -methyl-4- piperidyl)quinolin-4-amine;2,2,2-trifluoroacetic acid To a solution of intermediate l-09a (100 mg, 0.42 mmol) in DME (5 ml_) was added K3PO4 (0.26 g, 1 .26 mmol), Biphenyl-2-yl-dicyclohexyl-phosphane (0.022 g, 0.063 mmol), Pd2(dba)3 (0.57 , 0.063 mmol), 1 -methylpiperidin-4- amine (R-03a) (0.24 g, 2.1 mmol), the mixture was heated to 1 10 °C for 3h under microwave. The solution was concentrated and extracted with AcOEt. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the crude product which was purified by prep-HPLC (General procedure, Method 1 ) to give compound 3-01 as TFA salt (0.02 g, 0.15% yield). ESI-MS (M+1 ): 316.2 calc. for C18H25N3O2. C2HF3O2: 429.2; Rt is 1 .54.

Reference： [1]Current Patent Assignee: FUNDACION PARA LA INVESTIGACION MEDICA APLICADA - WO2015/192981, 2015, A1 Location in patent: Page/Page column 49; 58

Yield	Reaction Conditions	Operation in experiment
22%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In 1,4-dioxane; water at 110℃; for 3h; Microwave irradiation;	Preparation of intermediate l-05a: 4-chloro-6-methoxy-2-methyl-7-(3-pyrrolidin-1-ylpropoxy)quinoline General procedure: To A solution of intermediate l-04a (1 .6 g, 4.52 mmol) in 1 ,4-dioxane/H20 (10:1 , 1 1 mL) was added K2C03(1 .25 g, 9.04 mmol), Pd(PPh3)4(0.53 g, 0.452 mmol) and methylboronic acid (R-02a, 0.30 g, 4.98 mmol) and the solution was heated to 1 10 °C for 3 hours under Microwave. Then the mixture was concentrated and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2S04.filtered and concentrated to give the crude product which was purified by column chromatography (Si02, DCM/MeOH = 1 :0 to 4:1 ) to give pure intermediate l-05a (0.18 g, 12%) as a yellow solid. ESI-MS (M+1 ): 335 calc. for Ci8H23CIN202: 334.1 .

6
[ 100122-02-9 ]
[ 24313-88-0 ]
6,7-dimethoxy-2-methyl-N-(3,4,5-trimethoxyphenyl)quinolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In ethanol for 18h; Reflux;	General procedure for the synthesis of 4-anilinoquin(az)olines General procedure: 4-chloroquin(az)oline derivative (1.0 eq.), aniline derivative (1.1 eq.), were suspended in ethanol (10 mL) and refluxed for 18 h. The crude mixture was purified by flash chromatography using EtOAc:hexane followed by 1-5 % methanol in EtOAc; After solvent removal under reduced pressure, the product was obtained as a free following solid or recrystallized from ethanol/water. Compounds 6-54 were synthesized as previous described32 and 60-61 as previously reported.28.

Reference： [1]Saul, Sirle; Pu, Szu-Yuan; Zuercher, William J.; Einav, Shirit; Asquith, Christopher R.M. [Bioorganic and Medicinal Chemistry Letters, 2020, vol. 30, # 16]

7
[ 55717-45-8 ]
[ 100122-02-9 ]
4-((6-bromopyridin-3-yl)oxy)-6,7-dimethoxy-2-methylquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap In chlorobenzene at 110℃;	51.B Step B: A mixture of 4-chloro-6,7-dimethoxy-2-methylquinoline (0.144 g, 0.606 mmol), 2-bromo-5-hydroxypyridine (0.1 16 g, 0.666 mmol) and DMAP (0.00370 g, 0.0303 mmol) in chlorobenzene (1 .2 mL), was heated to 1 10 °C overnight. The mixture was cooled and partitioned between water (50 mL) and DCM (3 x 50 mL). The organic layers were combined, washed with brine (15 mL), dried over Na2S04, filtered and concentrated in vacuo to obtain crude 4-((6-bromopyridin-3-yl)oxy)-6,7-dimethoxy-2-methylquinoline (0.220 g, 0.586 mmol, 96.8 % yield).

Reference： [1]Current Patent Assignee: PFIZER INC - WO2020/141470, 2020, A1 Location in patent: Paragraph 001172-001174; 001176

8
[ 55717-45-8 ]
[ 100122-02-9 ]
5-((6,7-dimethoxy-2-methylquinolin-4-yl)oxy)pyridin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dmap / chlorobenzene / 110 °C 2: lithium hexamethyldisilazane; CyJohnPhos; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / tetrahydrofuran / 1 h / 80 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: PFIZER INC - WO2020/141470, 2020, A1

9
[ 603954-49-0 ]
[ 100122-02-9 ]
ethyl 2-[4-[[(6,7-dimethoxy-2-methyl-4-quinolyl)amino]methyl]-1-piperidyl]pyrimidine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In 1,4-dioxane at 120℃; for 48h; Inert atmosphere;

Reference： [1]Rabal, Obdulia; San José-Enériz, Edurne; Agirre, Xabier; Sánchez-Arias, Juan Antonio; De Miguel, Irene; Ordoñez, Raquel; Garate, Leire; Miranda, Estíbaliz; Saéz, Elena; Vilas-Zornoza, Amaia; Pineda-Lucena, Antonio; Estella, Ander; Zhang, Feifei; Wu, Wei; Xu, Musheng; Prosper, Felipe; Oyarzabal, Julen [Journal of Medicinal Chemistry, 2021, vol. 64, # 6, p. 3392 - 3426]

10
[ 100122-02-9 ]
2-[4-[[(6,7-dimethoxy-2-methyl-4-quinolyl)amino]methyl]-1-piperidyl]pyrimidine-5-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 48 h / 120 °C / Inert atmosphere 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 20 °C 2.2: pH 6

11
[ 100122-02-9 ]
2-[4-[[(6,7-dimethoxy-2-methyl-4-quinolyl)amino]methyl]-1-piperidyl]-N-tetrahydropyran-2-yloxy-pyrimidine-5-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 48 h / 120 °C / Inert atmosphere 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 20 °C 2.2: pH 6 3.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

12
[ 100122-02-9 ]
2-[4-[[(6,7-dimethoxy-2-methyl-4-quinolyl)amino]methyl]-1-piperidyl]pyrimidine-5-carbohydroxamic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 48 h / 120 °C / Inert atmosphere 2.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 16 h / 20 °C 2.2: pH 6 3.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere 4.1: hydrogenchloride / ethyl acetate / 16 h / 20 °C

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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
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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
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H316	Causes mild skin irritation
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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. 100122-02-9 ]

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Application In Synthesis of [ 100122-02-9 ]

[ 100122-02-9 ] Synthesis Path-Downstream 1~12

Related Parent Nucleus of [ 100122-02-9 ]

Quinolines

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