[ CAS No. 924304-73-4 ] {[proInfo.proName]}

Name: 924304-73-4|4-Chloroisoindoline hydrochloride|98%
Brand: Ambeed
SKU: A511321
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2D 3D

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Quality Control of [ 924304-73-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 924304-73-4 ]

SDS Specification

Alternatived Products of [ 924304-73-4 ]

Product Details of [ 924304-73-4 ]

CAS No. :	924304-73-4	MDL No. :	MFCD11110370
Formula :	C₈H₉Cl₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BHGGKDRWZHDWRI-UHFFFAOYSA-N
M.W :	190.07	Pubchem ID :	42609644
Synonyms :

Calculated chemistry of [ 924304-73-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.95
TPSA :	12.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.29
Log Po/w (WLOGP) :	2.06
Log Po/w (MLOGP) :	2.37
Log Po/w (SILICOS-IT) :	2.86
Consensus Log Po/w :	1.91

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.86
Solubility :	0.26 mg/ml ; 0.00137 mol/l
Class :	Soluble
Log S (Ali) :	-2.18
Solubility :	1.26 mg/ml ; 0.0066 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.6
Solubility :	0.0479 mg/ml ; 0.000252 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.48

Safety of [ 924304-73-4 ]

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 [ 924304-73-4 ]

* 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 [ 924304-73-4 ]

[ 924304-73-4 ] Synthesis Path-Downstream 1~20

1
[ 924304-73-4 ]
[ 924305-13-5 ]
[ 530-62-1 ]
[ 1078626-63-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With N-ethyl-N,N-diisopropylamine; In toluene; at 60℃;Product distribution / selectivity;	Step 4: Synthesis of (3J?,5S)-1-((S)-4-(but-3-enyIoxy)-2-(tert- butoxycarbonylamino)butanoyl)-5-((li?,25)-1-(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chIoroisoindoline-2-carboxylate[0489] (17?,25)-ethyl l-((25,4i)-1-((5)-4-(but-enyloxy)-2-(tert- butoxycarboalphaylamino)butanoyl)-4-hydroxypyrrolidine-2-carboxamido)-2- vinylcyclopropanecarboxylate (0.55 g, 1.1 mmol) in THF (20 mL) was added 1,1 '- carbonyldiimidazole (0.204 g, 1.26 mmol) in one portion. The reaction was stirred at room temperature for 3 hours. To the reaction was then added the N-ethyl-N-isopropylpropan-2- amine (0.92 mL, 5.3 mmol), followed by <strong>[924304-73-4]4-chloroisoindoline hydrochloride</strong> (0.258 g, 1.37 mmo.). The reaction was stirred at 50 C for 18 hours. The solvent was removed. The residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate solution. <n="164"/>The organic layer was separated and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (HexanerEthyl acetate=l :3) to give (3i?,5£)-1-((S)-4- (but-3-enyloxy)-2-(tert-butoxycarbonylamino)butanoyi)-5-(( IR,2S)- 1 -(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate as white solid (0.49 g, 66%). MS: Calcd.: 702.3; Found: [M+H]+ 703.1.
66%		Step 4: Synthesis of (3J?,5S)-1-((S)-4-(but-3-enyIoxy)-2-(tert- butoxycarbonylamino)butanoyl)-5-((li?,25)-1-(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chIoroisoindoline-2-carboxylate[0489] (17?,25)-ethyl l-((25,4i)-1-((5)-4-(but-enyloxy)-2-(tert- butoxycarboalphaylamino)butanoyl)-4-hydroxypyrrolidine-2-carboxamido)-2- vinylcyclopropanecarboxylate (0.55 g, 1.1 mmol) in THF (20 mL) was added 1,1 '- carbonyldiimidazole (0.204 g, 1.26 mmol) in one portion. The reaction was stirred at room temperature for 3 hours. To the reaction was then added the N-ethyl-N-isopropylpropan-2- amine (0.92 mL, 5.3 mmol), followed by <strong>[924304-73-4]4-chloroisoindoline hydrochloride</strong> (0.258 g, 1.37 mmo.). The reaction was stirred at 50 C for 18 hours. The solvent was removed. The residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate solution. <n="164"/>The organic layer was separated and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (HexanerEthyl acetate=l :3) to give (3i?,5£)-1-((S)-4- (but-3-enyloxy)-2-(tert-butoxycarbonylamino)butanoyi)-5-(( IR,2S)- 1 -(ethoxycarbonyl)-2- vinylcyclopropylcarbamoyl)pyrrolidin-3-yl 4-chloroisoindoline-2-carboxylate as white solid (0.49 g, 66%). MS: Calcd.: 702.3; Found: [M+H]+ 703.1.

Reference： [1]Patent: WO2008/137779,2008,A2 .Location in patent: Page/Page column 161-162
[2]Patent: WO2008/137779,2008,A2 .Location in patent: Page/Page column 161-162

2
[ 924304-73-4 ]
[ 74844-91-0 ]
[ 530-62-1 ]
[ 923590-72-1 ]

Yield	Reaction Conditions	Operation in experiment
91%		Compound 26; Step 2: Synthesis of (2S,4R)-1-(tert-butoxycarbonyl)-4-(4-chloroisoindoline-2- carbonyloxy)pyrrolidine-2-carboxylic acid; To a solution of (25",4lambda)-1-tert-butyI 2-methyl 4-hydroxypyitauolidme-1,2- dicarboxylate (500 mg, 2 04 mmol) in dry THF (6 mL) was added CDI (430 mg, 2 65 mmol) m one portion and the mixture was stirred at rt for 6 h The amine, 4-chloroisomdoline hydrochloride (0 89 g, 4 7 mmol) was then added in portions, followed by slow addition of DIEA (1 07 mL, 6.12 mmol). The reaction was stirred at rt for overnight. The reaction was diluted with 120 mL EtOAc, washed with IN HCl (2 x 50 mL), water and brine (50 mL each), and dried over Na2SO4 and concentrated down to a thick brownish oil The crude was purified by silica chromatography (eluent = hexanes/EtOAc 2 1), giving the ester product, (25,4J?)-1-tert-butyl 2-methyl 4-(4-chloroisoindolme-2-carbonyloxy)pyrrolidine-1,2- dicaiboxylate, as a light pinkish foamy solid (0 79 g, 91 % yield); (25',4R)-1-(tert-butoxycarbonyl)-4-(4-chloroisoindoIine-2-carbonyloxy)pyrrolidine-2- carboxylic acid; To a solution of (2S,4R)- 1 -tert-butyl 2-methyl 4-hydroxypyrrolidine-1,2- dicarboxylate (0.50 g, 2.04 mmol) in dry THF (6 niL) was added CDI (430 mg, 2.65 mmol) in one portion and the mixture was stirred at rt for 6 h. <strong>[924304-73-4]4-chloroisoindoline hydrochloride</strong> (0.89 g, 4.69 mmol) was then added in portions, followed by slow addition of DIEA (1.07 mL, 6.12 mmol). The reaction was stirred at rt for overnight. The reaction was diluted with 120 mL EtOAc, washed with IN HCl (2 x 50 mL), water and brine (50 mL each), and dried over Na2SC>4 and concentrated down to a thick brownish oil. The crude was purified by silica chromatography (eluent = hexanes/EtOAc 2: 1), giving (2S,4R)-1-tert-butyl 2-methyl 4-(4- chloroisoindoIine-2-carbonyloxy)pyrrolidine-l ,2-dicarboxylate as a light pinkish foamy solid (0.79 g, 91 % yield).

Reference： [1]Patent: WO2008/141227,2008,A1 .Location in patent: Page/Page column 106-107; 149-150

3
[ 924304-73-4 ]
[ 924305-09-9 ]
[ 530-62-1 ]
[ 1078626-39-7 ]

Yield	Reaction Conditions	Operation in experiment
86%		Step 3: Synthesis of (2Jff,65>,13a5',14ai?,16a5rZ)-ethyI 6-(tert-butoxycarbonylamino)-2-(4- chloroisoindoline-2~carbonyloxy)-5,16-dioxo-2,3,5,6,7,8,9,ll,13a,14,14a,15,16,16a- tetradecahydro-lH-cyclopropa(e)pyrrolo[2,l-i][l,7,10joxadiazacyclopentadecine-14a- carboxylate[0472] (2R,6S, 13aS, 14aR, 16aS,Z)-ethyl 6-(tert-butoxycarbonylamino)-2-hydroxy- 5,16-dioxo~2,3,5,6,7,8,9,l l,13a,14,14a,15,16,16a4etradecahydro-1H- cyclopropa(e)pyrrolo[2,l-/][l,7,10]oxadiazacyciopentadecine-14a-carboxylate (0.30 g, 0.61 mmol) in toluene (5 mL) was added lj '-carbonyldiimidazole (0.12 g, 0.73 ramol) in one portion. The reaction was stirred at room temperature for 3 hours. To the reaction was then added the N-ethyl-N-isopropylpropan-2-amine (0.53 mL, 3.0 mmol), followed by 4- chloroisoindoline hydrochloride salts (0.15 g, 0.79 mmol). The reaction was stirred at 60 C for 3 hours. The solvent was removed. The residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. After removal of solvent, the residue was purified by chromatography (etaexanerEthyl acetate=l:3) to give (2/?,65,13a5,14aR,16a5',Z)-ethyI 6-{tert- butoxycarbonylamino)-2-(4-chloroisoindoline-2-carbonyloxy)-5,16-dioxo- 2,3,5,6,7,8,9,11, 13a,14,14a,15,16,16a-tetradecahydro-1H-cyclopropa(phiyrrolo[2,l- /][l,7,10]oxadiazacyclopentadecine-14a-carboxylate as white solid (0.18 g, 86%). MS: Calcd.: 674.3; Found: [M+eta]+ 675.1.

Reference： [1]Patent: WO2008/137779,2008,A2 .Location in patent: Page/Page column 139

4
[ 924304-73-4 ]
[ 1083091-89-7 ]