[ CAS No. 1344701-44-5 ] {[proInfo.proName]}

Name: 1344701-44-5|6-Hydroxy-2-methylisoindolin-1-one|97%
Brand: Ambeed
SKU: A158831
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Quality Control of [ 1344701-44-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1344701-44-5 ]

SDS Specification

Alternatived Products of [ 1344701-44-5 ]

Product Details of [ 1344701-44-5 ]

CAS No. :	1344701-44-5	MDL No. :	MFCD20441063
Formula :	C₉H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NSDPMSCJMHMIKP-UHFFFAOYSA-N
M.W :	163.17	Pubchem ID :	70310067
Synonyms :

Calculated chemistry of [ 1344701-44-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.32
TPSA :	40.54 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.49
Log Po/w (XLOGP3) :	0.6
Log Po/w (WLOGP) :	0.45
Log Po/w (MLOGP) :	0.84
Log Po/w (SILICOS-IT) :	1.23
Consensus Log Po/w :	0.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.6
Solubility :	4.1 mg/ml ; 0.0251 mol/l
Class :	Very soluble
Log S (Ali) :	-1.03
Solubility :	15.4 mg/ml ; 0.0944 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.98
Solubility :	1.72 mg/ml ; 0.0106 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.26

Safety of [ 1344701-44-5 ]

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 [ 1344701-44-5 ]

* 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 [ 1344701-44-5 ]

[ 1344701-44-5 ] Synthesis Path-Downstream 1~11

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide In methanol at 25℃; for 16h;	Step 2: Methyl 2-(5-hydroxy-1H-indazol-1-yl)acetate General procedure: To a solution of methyl methyl 2-(1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazol-3-yl)acetate (200 mg, 0.606 mmol) in MeOH (4 mL) was added H2O2 (35%, 0.265 mL, 3.03 mmol). The mixture was stirred at 25° C. for 16 h. The reaction was quenched with aqueous, saturated Na2SO3 (10 mL) and then partitioned with water (10 mL) and EtOAc (20 mL×3). The combined organic phases were washed brine (5 mL), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by reverse phase HPLC (ACN/water with 0.1% TFA modifier) to afford the title compound. MS: 221 (M+1).
	With water; dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0℃; for 0.5h;	Step 2: l-(Cvclopropylmethyl)-lH-pyrazol-4-ol General procedure: To a solution of l-(cyclopropylmethyl)-4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lH-pyrazole (500 mg, 2.02 mmol) and NaOH (161 mg, 4.03 mmol) in THF (5 mL) at 0 °C was added hydrogen peroxide (30%, 457 mg, 4.03 mmol). After 30 min at 0 °C, the mixture was diluted with aqueous NaHSC^ (saturated, 20 mL) and extracted with EtOAc (70 mL x 3). The combined organic layers were washed with water (40 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (100:0-5: 1 petroleum ether/ EtOAc) to give the title compound. XH NMR (400 MHz, CDC13): δ 6.89 (1 H, s), 6.87 (1 H, s), 3.55 (2 H, d, J = 6.8 Hz), 2.15 (1 H, br s), 0.30 (2 H, d, J = 7.2 Hz), 0.21 (2 H, d, J= 5.2 Hz).

2
[ 5292-43-3 ]
[ 1344701-44-5 ]
[ 2319646-64-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 2.5h;	596.596A Example 596A: tert-butyl 2-((2-methyl-3-oxoisoindolin-5-yl)oxy)acetate To a solution of 6-hydroxy-2-methylisoindolin-l-one (0.50 g, 3.1 mmol) in N,N- dimethylformamide (3.6 mL) at ambient temperature was added potassium carbonate (0.847 g, 6.13 mmol) and teri-butyl bromoacetate (0.52 mL, 3.5 mmol). This mixture was warmed to 70 °C and was allowed to stir for 2.5 hours. Then the mixture was allowed to cool to ambient temperature and was diluted with ethyl acetate (50 mL) and water (50 mL). The layers were separated, and the aqueous layer was extracted with ethyl acetate (3 x 15 mL). The combined organic layers were dried over anhydrous Na2SO/t, filtered, and concentrated under reduced pressure to give the title compound (0.85 g, 3.1 mmol, quantitative yield), which was carried forward without purification. JH NMR (501 MHz, DMSO- 7.14 (dd, J = 8.3, 2.5 Hz, 1H), 7.10 (d, J = 2.4 Hz, 1H), 4.74 (s, 2H), 4.37 (s, 2H), 3.06 (s, 3H), 1.42 (s, 9H); MS (ESI+) m/z 278 (M+H)+.

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2019/90069, 2019, A1 Location in patent: Page/Page column 530

3
[ 1344701-44-5 ]
[ 2319646-65-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2019/90069, 2019, A1

4
[ 1344701-44-5 ]
[ 2319646-66-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2019/90069, 2019, A1

5
[ 1344701-44-5 ]
[ 2319646-67-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2019/90069, 2019, A1

6
[ 1344701-44-5 ]
[ 2319643-88-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 3: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 20 °C 5: triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / N,N-dimethyl-formamide / 20 °C

Reference： [1]Current Patent Assignee: ABBVIE INC - WO2019/90069, 2019, A1

7
[ 1254319-51-1 ]
[ 1344701-44-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate / 1,4-dioxane / 1.5 h / 80 °C 2: sodium hydroxide; dihydrogen peroxide / tetrahydrofuran / 0.5 h / 0 °C

Reference： [1]Current Patent Assignee: SHANGHAI APEIRON BIOTECHNOLOGY - CN113234079, 2021, A

8
[ 1313399-38-0 ]
[ 1344701-44-5 ]

Yield	Reaction Conditions	Operation in experiment
93.54%	With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0℃; for 0.5h;	25.2 Step 2: Synthesis6-Hydroxy-2-methyl-2,3-dihydro-1H-isoindol-1-one (25-4) The 2-methyl-6-(tetramethyl-1,3,2-dioxolane-2-yl)-2,3-dihydro-1H-isoindol-1-one (1.7g, 6.224 mmol)And sodium hydroxide (0.50g, 12.448mmol)Dissolved in tetrahydrofuran (50mL),The reaction mixture is reduced to 0°C and addedHydrogen peroxide (1.21 g, 12.448 mmol).The mixture was stirred and reacted at 0°C for 30 minutes.The reaction solution was poured into saturated sodium bisulfite aqueous solution (150 mL),Extract with ethyl acetate (200mL),The extract is dried with anhydrous sodium sulfate,Filter to remove anhydrous sodium sulfate,Crude product by silica gel column chromatography(Petroleum ether: ethyl acetate = 80:20 (v/v))Purified the target product as a red solid(950 mg, 5.822 mmol, 93.54% yield).

Reference： [1]Current Patent Assignee: SHANGHAI APEIRON BIOTECHNOLOGY - CN113234079, 2021, A Location in patent: Paragraph 0497; 0498; 0502; 0503; 0504

9
[ 1344701-44-5 ]
[ 2718254-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 2: ammonium hydroxide / tetrahydrofuran; isopropyl alcohol / 48 h / 85 °C

Reference： [1]Current Patent Assignee: SHANGHAI APEIRON BIOTECHNOLOGY - CN113234079, 2021, A

10
[ 1344701-44-5 ]
[ 2718254-08-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 2: ammonium hydroxide / tetrahydrofuran; isopropyl alcohol / 48 h / 85 °C 3: trifluoroacetic acid / water / 5 h

Reference： [1]Current Patent Assignee: SHANGHAI APEIRON BIOTECHNOLOGY - CN113234079, 2021, A

11
[ 2086765-78-6 ]
[ 1344701-44-5 ]
[ 2718254-69-2 ]

Yield	Reaction Conditions	Operation in experiment
71.11%	With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	25.3 Step 3: Synthesis6-[(3aR,4R,6R,6As)-6-{4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2,2-dimethyl-hexahydro Pent[d][1,3]dioxool-4-yl]methoxy}-2-methyl-2,3-dihydro-1H-isoindol-1-one (25-5) The compound [(3aR,4R,6R,6As)-6-{4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl}-2,2-dimethyl-hexahydrocyclopenta [d][1,3]dioxo-4-yl]methyl 4-toluene-1-sulfonate (430mg, 0.900mmol)Dissolve in DMF (4mL).Add cesium carbonate (879.87mg, 2.699mmol)And 6-hydroxy-2-methyl-2,3-dihydro-1H-isoindol-1-one (161.48 mg, 0.990 mmol).The mixture was stirred at room temperature for 16 hours.Pour the reaction solution into water (30mL),Extract with ethyl acetate (70mL),The extract is dried with anhydrous sodium sulfate,Filter to remove anhydrous sodium sulfate,Chromatography on silica gel column (petroleum ether: ethyl acetate=50:50(v/v))After purification, a yellow oily target product is obtained(300mg, 0.640mmol, yield 71.11%).

Reference： [1]Current Patent Assignee: SHANGHAI APEIRON BIOTECHNOLOGY - CN113234079, 2021, A Location in patent: Paragraph 0497; 0498; 0505; 0506; 0507

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Ghs Precautionary Statements

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Physical hazards
Code	Phrase
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
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H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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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
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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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Health hazards
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H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
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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. 1344701-44-5 ] {[proInfo.proName]}

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[ 1344701-44-5 ] Synthesis Path-Downstream 1~11

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Indolines

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