114041-16-6|5,6-Dimethoxyisoindoline| Ambeed

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Quality Control of [ 114041-16-6 ] Purity: 95% SDS Specification

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Product Details of [ 114041-16-6 ]

CAS No. :	114041-16-6
Formula :	C₁₀H₁₃NO₂
M.W :	179.22
SMILES Code :	COC1=CC2=C(C=C1OC)CNC2
MDL No. :	MFCD08234863
InChI Key :	WMIINIMCTOCKNL-UHFFFAOYSA-N
Pubchem ID :	20074351

Safety of [ 114041-16-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 114041-16-6 ]

* 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 [ 114041-16-6 ]
Downstream synthetic route of [ 114041-16-6 ]

[ 114041-16-6 ] Synthesis Path-Upstream 1~4

1
[ 114041-14-4 ]
[ 60-29-7 ]
[ 114041-16-6 ]

References: [1] Patent: US4987235, 1991, A, .

2
[ 1427927-32-9 ]
[ 114041-16-6 ]

References: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 934 - 946.
[2] Patent: WO2013/39854, 2013, A1, . Location in patent: Page/Page column 39.

3
[ 91-16-7 ]
[ 114041-16-6 ]

References: [1] Patent: WO2013/39854, 2013, A1, .
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 934 - 946.

4
[ 26726-81-8 ]
[ 114041-16-6 ]

References: [1] Patent: WO2013/39854, 2013, A1, .
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 934 - 946.

[ 114041-16-6 ] Synthesis Path-Downstream 1~35

1
4-[6-bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene [ No CAS ]
[ 114041-16-6 ]
[ 642-30-8 ]
2-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]-heptyl]-1,2,3,4-tetrahydro-6,7,8-trimethoxyisoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 67 2-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]-heptyl]-1,2,3,4-tetrahydro-6,7,8-trimethoxyisoquinoline The procedure of Example 49 is repeated using 5.31 g 4-[6-bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene, 3.29 g of <strong>[114041-16-6]5,6-dimethoxyisoindoline</strong> and 2.65 g of 6,7,8-trimethoxy-1,2,3,4-tetrahydroisoquinoline. This affords 4.52 g of the desired product as a yellow oil.

References: [1]Patent: US5387685,1995,A .

2
[ 67-56-1 ]
4-[6-bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene [ No CAS ]
[ 114041-16-6 ]
2-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]-heptyl]-2,3-dihydro-5,6-dimethoxy-1H-isoindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In hexane; acetonitrile;	EXAMPLE 49 2-[7-(3,4-Dimethoxyphenyl)-7-[(4-methylphenyl)thio]-heptyl]-2,3-dihydro-5,6-dimethoxy-1H-isoindole A mixture of 1.79 g of 4-[6-bromo-1-[(4-methylphenyl)thio]heptyl]-1,2-dimethoxybenzene, 3.29 g of <strong>[114041-16-6]5,6-dimethoxyisoindoline</strong>, 25 mL of acetonitrile, and 1.74 mL of N,N-diisopropylethylamine is heated under reflux for 2 days. The reaction is concentrated in vacuo and the black residue partitioned between chloroform and aqueous ammonia. The organic layer is dried (sodium sulfate) and the solvent removed at reduced pressure. Chromatography on silica gel with gradient elution progressing from hexane to chloroform to methyl alcohol, twice, gives 1.34 g of the desired product as a brown gum. MS(Hi res): m/z Calcd for C32 H41 NO4 S 535.2756 Found 535.2723 Calcd for C32 H41 NO4 S H2 O C=69.41, H=7.83, N=2.53, S=5.78 Found C=69.59, H=7.51, N=2.53, S=6.19

References: [1]Patent: US5387685,1995,A .

3
[ 114041-14-4 ]
[ 60-29-7 ]
[ 114041-16-6 ]

Yield	Reaction Conditions	Operation in experiment
77.3%	palladium-carbon; In methanol; ethyl acetate;	EXAMPLE 11 Preparation of 5,6-dimethoxyisoindoline 1.20 g (4.46 mmol) of 2-benzyl-5,6-dimethoxyisoindoline was dissolved in 40 ml of methanol at 40 C., and 84 mg of 10% palladium carbon was added thereto. Under a hydrogen stream, catalytic reduction was conducted at the same temperature for 4 hours. The solvent was distilled off under reduced pressure, and a small amount of ethyl acetate and diethylether was added to the residue and stirred. The precipitates were collected to obtain 617 mg (yield: 77.3%) of the above identified compound. Melting point: 131 C. (decomposed) IRnu(KBr): 3360, 3100-2500, 1610, 1500, 1460, 1270, 1210, 1090, 850, 740, 680cm-1 NMRdelta(CDCl3): 2.54(1H, s), 3.87(6H, s), 4.18 (4H, s), 6.77(2H, s)

References: [1]Patent: US4987235,1991,A .

4
[ 114041-16-6 ]
5,6-dihydroxyisoindoline hydrobromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
520 mg (80.3%)	With hydrogen bromide;	EXAMPLE 13 Preparation of 5,6-dihydroxyisoindoline hydrobromide 3.54 ml of 48% hydrobromic acid was added to 500 mg (2.79 mmol) of <strong>[114041-16-6]5,6-dimethoxyisoindoline</strong>, and the mixture was refluxed for 3 hours under stirring. The precipitated crystals were collected, and washed with ethanol/diethyl ether (1/1) to obtain 520 mg (80.3%) of the above identified compound. The melting point, the infrared absorption spectrum and the 1 H-NHR spectrum of this product were the same as those of the compound of Example 8.

References: [1]Patent: US4987235,1991,A .

5
[ 3934-20-1 ]
[ 114041-16-6 ]
[ 1107627-07-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 3h;	Compound 427:Dichloropyrimidine (298 mg, 2.0 mmol) was dissolved in dry THF (10 ml_) with Et3N (280 uL, 2.0 mmol). The mixture was cooled to 0 C, and isoindoline (380 mg, 2.1 mmol) was added. The resulting mixture was warmed to room temperature and stirred for 3 hours. The EtOAc was added to dilute the mixture and the organics was washed with water, brine and dried over Na2SO4. After concentration, the residue was purified with column (silica gel, EtOAc/Hexane = 30:70) to give the product 427 (311 mg) as light yellow solid. HPLC-MS tR = 1.49 min (UV254 nm); mass calculated for formula C14H14CIN3O2 291.1 , observed LCMS m/z 292.1 (M+H).

References: [1]Patent: WO2009/14637,2009,A2 .Location in patent: Page/Page column 178.

6
[ 114041-16-6 ]
[ 1107626-41-4 ]
[ 1107626-42-5 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 80℃; for 1h;	Compound 250:2-chloropyrimidine derivative 249 (50 mg) and isoindoline (50 mg) were dissolved in Acetonitrile (5 mL) and the mixture was heated to 80 C and stirred for 1 hour. The solvent was removed by concentration and the residue was purified by Prep-LC gave compound 250. HPLC-MS tR = 1.63 min (UV254 nm); mass calculated for formula 029H35N7O5 561.3, observed LCMS m/z 562.3 (M+H).

References: [1]Patent: WO2009/14637,2009,A2 .Location in patent: Page/Page column 128-129.

7
[ 114041-16-6 ]
C₁₉H₂₀ClN₇O₃ [ No CAS ]
C₂₉H₃₂N₈O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile; at 100℃; for 0.5h;Microwave irradiation;	Compound 416 :In a 10 mL microwave tube, compound 415 (100 mg, 0.23 mmol) was combined with <strong>[114041-16-6]5,6-dimethoxyisoindoline</strong> (42 mg, 0.23 mmol), triethylamine (69 mg, 0.69 mmol) and acetonitrile (2 mL). The solution was irradiated for 30 minutes at 100 C, then diluted with EtOAc and filtered over a short plug of silica gel, rinsing with EtOAc, to afford the intermediate compound 416. HPLC- MS tR = 1.71 min (UV254 nm); Mass calculated for C24H24N8O3: 572.3; Observed m/z: 573.3 (M+H).

References: [1]Patent: WO2009/14637,2009,A2 .Location in patent: Page/Page column 171; 173.

8
[ 114041-16-6 ]
[ 888855-12-7 ]
[ 888725-11-9 ]

Yield	Reaction Conditions	Operation in experiment
		Step e: simultaneous preparation of 1-(5,6-dimethoxyisoindolin-2-yl)-6-[4-(3-trifluoromethyl-phenyl)piperazin-1-yl]hexan-1-one, 1-isoindolin-2-yl-6-[4-(2-cyanophenyl)piperazin-1-yl]hexan-1-one and 1-isoindolin-2-yl-6-[4-(2-methyl-phenyl)piperazin-1-yl]hexan-1-one A mixture of 0.3 mmol of dicyclohexylcarbodiimide and 0.3 mmol of 1-hydroxybenzotriazole is added to a solution of acid (0.3 mmol) in 2 mL of anhydrous N,N-dimethylformamide. The mixture is left whilst stirring for four hours at 70 C. It is then cooled at ambient temperature, filtered in order to eliminate the dicyclohexylurea. Amine (0.2 mmol) is then added, then it is left for twenty hours at ambient temperature. The N,N-dimethylformamide is evaporated out in a vacuum and the crude is taken up by 2 mL of dichloromethane. It is then washed twice with 1 mL of a normal aqueous solution of soda, then with 1 mL of water. The organic phase is dried then concentrated in a vacuum. Starting from 6-[4-(3-trifluoromethyl-phenyl)piperazin-1-yl]hexanoic acid and <strong>[114041-16-6]5,6-dimethoxyisoindoline</strong>, 1-(5,6-dimethoxyisoindolin-2-yl)-6-[4-(3-trifluoromethylphenyl)piperazin-1-yl]hexan-1-one is obtained in this way. Rf: 0.76 dichloromethane/methanol 85/15

References: [1]Patent: US2008/214542,2008,A1 .Location in patent: Page/Page column 25.

9
[ 114041-16-6 ]
[ 1258447-97-0 ]
N-(2-tert-butoxybenzyl)-6-(4-(2-methoxyphenyl)cyclohexyl)-N-(pyridin-2-ylmethyl)hexan-1-amine [ No CAS ]
N-(2-tert-butoxybenzyl)-6-(5,6-dimethoxyisoindolin-2-yl)-N-(pyridin-2-ylmethyl)hexan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In methanol; methanolic NH3; dichloromethane;	Example 17 N-(2-tert-butoxybenzyl)-6-(5,6-dimethoxyisoindolin-2-yl)-N-(pyridin-2-ylmethyl)hexan-1-amine [13] The same procedure as described for compound 11 was applied to starting material 10 (0.428 g, 0.988 mmol) and <strong>[114041-16-6]5,6-dimethoxyisoindoline</strong> (0.175 g, 0.975 mmol). Purification was carried out on a silica gel TLC plate that was developed in with a 5% methanolic NH3 (7 M NH3 in methanol/95% CH2Cl2. The product was isolated as pale yellow oil (60%). 1H NMR (CDCl3) delta 8.446 (dd, 1H, Ar), 7.72 (m, 3H, Ar), 7.062 (m, 2H, Ar), 6.981 (ddd, 2H, Ar), 6.888 (s, 2H, Ar), 3.816 (s, 4H, -CH2-CH2-), 3.792 (s, 6H, -OCH3-), 3.714 (s, 2H, -CH2-), 3.637 (s, 2H, -CH2-), 2.611 (t, 2H, -CH2-), 2.436 (t, 2H, -CH2-), 1.503 (m, 4H, -CH2-CH2-), 1.319 (s, 9H, -C(CH3)3), 1.275 (m, 4H, -CH2-CH2-). Mass Spec.=531.73 (M+H)+.

References: [1]Patent: US2012/269724,2012,A1 .

10
[ 85-42-7 ]
[ 114041-16-6 ]
[ 127946-77-4 ]
[ 1403499-41-1 ]

References: [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 8827 - 8837,11.

11
[ 91-16-7 ]
[ 114041-16-6 ]

References: [1]Patent: WO2013/39854,2013,A1 .
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 934 - 946.

12
[ 26726-81-8 ]
[ 114041-16-6 ]

References: [1]Patent: WO2013/39854,2013,A1 .
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 934 - 946.

13
[ 1427927-32-9 ]
[ 114041-16-6 ]

Yield	Reaction Conditions	Operation in experiment
		Step 5) The compound 7 (211 mg, 0.45 mmol) was dissolved in the mixture of MeOH/CHCl3 (5 mL/5 mL) and cooled to 0C. TFA (10 mL) was added carefully. After 5 minutes at 0C, the mixture was warmed to room temperature and stirred for another 30 minutes. After concentration, the residue was taken in ether and 1 N HC1. The aqueous was extracted with ether and then basified with 4 N NaOH to pH ~10. The mixture was extracted with DCM (40 mL x 3). The combined organic phase were dried and concentrated. The crude product 8 (81 mg) was used in the next step directly without further purification.

References: [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 934 - 946.
[2]Patent: WO2013/39854,2013,A1 .Location in patent: Page/Page column 39.

14
[ 114041-16-6 ]
2-(1,3-dihydro-5,6-dimethoxy-2H-isoindol-2-yl)-N-[4-(1-piperazinyl)-3-pyridinyl]-4-pyrimidinecarboxamide hydrochloride [ No CAS ]

References: [1]Patent: WO2013/39854,2013,A1 .

15
[ 114041-16-6 ]
[ 1427927-38-5 ]

References: [1]Patent: WO2013/39854,2013,A1 .

16
[ 114041-16-6 ]
[ 1107626-42-5 ]

References: [1]Patent: WO2013/39854,2013,A1 .

17
[ 114041-16-6 ]
[ 75833-38-4 ]
[ 1427927-36-3 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile; at 80℃; for 1h;	Step 8) 2-c oropyrimidine derivative 11 (5.84 g, 42.0 mmol), DIEA (8 mL, 46 mmol) and isoindoline (7.52 mg, 42.0 mmol) were dissolved in Acetonitrile (100 mL) and the mixture was heated to 80C and stirred for 1 hour. The solvent was removed by concentration and water was added. The solid was collected with filtration, washed with water and dried under air. The crude 12 was used in the next step directly without further purification.

References: [1]Patent: WO2013/39854,2013,A1 .Location in patent: Page/Page column 40.

18
[ 114041-16-6 ]
C₁₈H₁₇BrFN [ No CAS ]
3-[4-(5,6-dimethoxyisoindolin-2-yl)butyl]-1-(4-fluorophenyl)-1H-indole [ No CAS ]

References: [1]MedChemComm,2015,vol. 6,p. 1093 - 1103.

19
[ 114041-16-6 ]
2-(5,6-dimethoxyisoindolin-2-yl)ethanamine [ No CAS ]