[ CAS No. 68634-02-6 ] {[proInfo.proName]}

Name: 68634-02-6|Methyl 1-oxo-2,3-dihydro-1H-indene-5-carboxylate|95%
Brand: Ambeed
SKU: A117800
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Quality Control of [ 68634-02-6 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 68634-02-6 ]

CAS No. :	68634-02-6	MDL No. :	MFCD09263429
Formula :	C₁₁H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YYKBHCRUMAMBPY-UHFFFAOYSA-N
M.W :	190.20	Pubchem ID :	10375253
Synonyms :

Calculated chemistry of [ 68634-02-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.27
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.77
TPSA :	43.37 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	1.52
Log Po/w (WLOGP) :	1.6
Log Po/w (MLOGP) :	1.49
Log Po/w (SILICOS-IT) :	2.6
Consensus Log Po/w :	1.85

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.31 mg/ml ; 0.00689 mol/l
Class :	Soluble
Log S (Ali) :	-2.04
Solubility :	1.74 mg/ml ; 0.00914 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.19
Solubility :	0.121 mg/ml ; 0.000638 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Safety of [ 68634-02-6 ]

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

Application In Synthesis of [ 68634-02-6 ]

* 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 [ 68634-02-6 ]
Downstream synthetic route of [ 68634-02-6 ]

[ 68634-02-6 ] Synthesis Path-Upstream 1~10

1
[ 68634-02-6 ]
[ 3470-45-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2018,

2
[ 67-56-1 ]
[ 201230-82-2 ]
[ 34598-49-7 ]
[ 68634-02-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 70℃; for 48 h;	A pressure vessel was charged with 5-bromo-2,3-dihydro-l H-inden-l-one (30 g, 142 mmol), methanol (400 mL), DMF (400 mL), triethylamine (72 g, 0.71 mol), diacetoxypalladium (3.2 g, 14 mmol) and l,3-bis(diphenylphosphino)propane (1 1.7 g, 24 mmol). The sealed vessel was pressurized with carbon monoxide at 50 Psi and heated at 70 °C for 48 h. The vessel was cooled and the reaction mixture was filtered through CELITE and rinsed with MeOH (500 mL). The combined filtrates were concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (petroleum ether: EtOAc=3: l) to afford methyl l-oxo-2,3-dihydro-l H-indene-5-carboxylate (20 g, 74percent) as a yellow solid. MS ESI calc'd. For C_u H₁₀O₃ [M + H] ⁺ 191, found 191.
67%	at 10℃; for 24 h;	Into a 1-L round-bottom flask was placed a solution of 5-bromo-2,3-dihydro-lH- inden-l-one (30 g, 142 mmol, 1 equiv) in MeOH (450 mL), Pd(dppf)Cl₂(15.6 g, 21.32 mmol, 0.15 equiv) and Et3N (57.5 g, 568 mmol, 4 equiv). CO (g) was introduced to the flask. The reaction mixture was stirred for 24 h at 100 °C in an oil bath, then cooled to room temperature. The solids were filtered and the filtrate was concentrated under vacuum. The residue was purified by normal phase chromatography on silica gel using EtOAc/petroleum ether (1:10). The collected fractions were concentrated under vacuum to afford 18 g (67percent yield) of the title compound as a yellow solid.

Reference： [1] Journal of Medicinal Chemistry, 2018,
[2] Patent: WO2014/74422, 2014, A1, . Location in patent: Paragraph 00201
[3] Patent: WO2017/218950, 2017, A1, . Location in patent: Paragraph 00325
[4] Patent: US2007/49603, 2007, A1, . Location in patent: Page/Page column 51

3
[ 91880-84-1 ]
[ 18107-18-1 ]
[ 68634-02-6 ]

Reference： [1] Patent: US2009/75996, 2009, A1, . Location in patent: Page/Page column 21

4
[ 86031-43-8 ]
[ 68634-02-6 ]
[ 68634-03-7 ]

Reference： [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1764 - 1768
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 19, p. 3717 - 3719

5
[ 65898-38-6 ]
[ 68634-02-6 ]

Reference： [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1764 - 1768
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 19, p. 3717 - 3719

6
[ 496-11-7 ]
[ 68634-02-6 ]

Reference： [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1764 - 1768

7
[ 4228-10-8 ]
[ 68634-02-6 ]

Reference： [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1764 - 1768

8
[ 15497-40-2 ]
[ 68634-02-6 ]

Reference： [1] Russian Journal of Organic Chemistry, 2002, vol. 38, # 12, p. 1764 - 1768

9
[ 67-56-1 ]
[ 3470-45-9 ]
[ 68634-02-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1978, vol. 26, p. 2475 - 2482

10
[ 186581-53-3 ]
[ 105469-25-8 ]
[ 105500-35-4 ]
[ 68634-02-6 ]
[ 129539-54-4 ]
[ 111057-60-4 ]

Reference： [1] Journal of Organic Chemistry, 1990, vol. 55, # 23, p. 5854 - 5861

[ 68634-02-6 ] Synthesis Path-Downstream 1~71

1
[ 186581-53-3 ]
[ 105469-25-8 ]
[ 105500-35-4 ]
[ 68634-02-6 ]
[ 129539-54-4 ]
[ 111057-60-4 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 5854 - 5861

2
[ 67-56-1 ]
[ 3470-45-9 ]
[ 68634-02-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1978,vol. 26,p. 2475 - 2482

3
[ 38622-91-2 ]
[ 68634-02-6 ]
[ 68634-04-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1978,vol. 26,p. 2475 - 2482

4
[ 86031-43-8 ]
[ 68634-02-6 ]
[ 68634-03-7 ]

Reference： [1]Russian Journal of Organic Chemistry,2002,vol. 38,p. 1764 - 1768
[2]Journal of Medicinal Chemistry,1995,vol. 38,p. 3717 - 3719

5
[ 151-50-8 ]
[ 68634-02-6 ]
[ 168560-81-4 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3717 - 3719

6
[ 143-33-9 ]
[ 506-87-6 ]
[ 68634-02-6 ]
2',4'-dioxoindan-1-spiro-5'-imidazolidine-5-carboxylic acid [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2002,vol. 38,p. 1764 - 1768

7
[ 68634-02-6 ]
[ 762-04-9 ]
[ 100-46-9 ]
1-benzylamino-1-(diethoxy-phosphoryl)-indan-5-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Synlett,2003,p. 2321 - 2324

8
[ 41879-39-4 ]
[ 68634-02-6 ]
[ 927806-65-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	toluene-4-sulfonic acid; In toluene; at 150℃; for 4h;	Step B: Preparation of methyl 1-(tert-butyldimethylsilyloxyimino)-2,3-dihydro-1H-indene-5-carboxylate: A 50 mL toluene solution containing <strong>[68634-02-6]methyl 1-oxo-2,3-dihydro-1H-indene-5-carboxylate</strong> (0.500 g, 2.63 mmol), TBS-ONH2 (0.387 g, 2.63 mmol) and catalytic toluenesulfonic acid (0.0500 g, 0.263 mmol) in a round bottom flask equipped with a Dean-Stark trap was heated to 150 C. for 4 hours and the solution azeotroped. The reaction mixture was concentrated, and the residue was taken up in ether, washed with water, dried over sodium sulfate, filtered and concentrated to an off-white solid. The solid was dissolved in CH2Cl2 and purified by column chromatography eluting with 100% hexanes-15% EtOAc/Hexanes. The desired product was isolated in 91% yield as a white solid.

Reference： [1]Patent: US2007/49603,2007,A1 .Location in patent: Page/Page column 51

9
[ 496-11-7 ]
[ 68634-02-6 ]

Reference： [1]Russian Journal of Organic Chemistry,2002,vol. 38,p. 1764 - 1768

10
[ 4228-10-8 ]
[ 68634-02-6 ]

Reference： [1]Russian Journal of Organic Chemistry,2002,vol. 38,p. 1764 - 1768

11
[ 65898-38-6 ]
[ 68634-02-6 ]

Reference： [1]Russian Journal of Organic Chemistry,2002,vol. 38,p. 1764 - 1768
[2]Journal of Medicinal Chemistry,1995,vol. 38,p. 3717 - 3719

12
[ 15497-40-2 ]
[ 68634-02-6 ]

Reference： [1]Russian Journal of Organic Chemistry,2002,vol. 38,p. 1764 - 1768

13
[ 68634-02-6 ]
1-aminoindan-1,5-dicarboxylic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 3717 - 3719

14
[ 68634-02-6 ]
[ 68634-06-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1978,vol. 26,p. 2475 - 2482

16
[ 67-56-1 ]
[ 201230-82-2 ]
[ 34598-49-7 ]
[ 68634-02-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; triethylamine; In N,N-dimethyl-formamide; at 70℃; under 2585.81 Torr; for 48h;	A pressure vessel was charged with 5-bromo-2,3-dihydro-l H-inden-l-one (30 g, 142 mmol), methanol (400 mL), DMF (400 mL), triethylamine (72 g, 0.71 mol), diacetoxypalladium (3.2 g, 14 mmol) and l,3-bis(diphenylphosphino)propane (1 1.7 g, 24 mmol). The sealed vessel was pressurized with carbon monoxide at 50 Psi and heated at 70 C for 48 h. The vessel was cooled and the reaction mixture was filtered through CELITE and rinsed with MeOH (500 mL). The combined filtrates were concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (petroleum ether: EtOAc=3: l) to afford methyl l-oxo-2,3-dihydro-l H-indene-5-carboxylate (20 g, 74%) as a yellow solid. MS ESI calc'd. For Cu H10O3 [M + H] + 191, found 191.
67%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; at 10℃; for 24h;	Into a 1-L round-bottom flask was placed a solution of 5-bromo-2,3-dihydro-lH- inden-l-one (30 g, 142 mmol, 1 equiv) in MeOH (450 mL), Pd(dppf)Cl2(15.6 g, 21.32 mmol, 0.15 equiv) and Et3N (57.5 g, 568 mmol, 4 equiv). CO (g) was introduced to the flask. The reaction mixture was stirred for 24 h at 100 C in an oil bath, then cooled to room temperature. The solids were filtered and the filtrate was concentrated under vacuum. The residue was purified by normal phase chromatography on silica gel using EtOAc/petroleum ether (1:10). The collected fractions were concentrated under vacuum to afford 18 g (67% yield) of the title compound as a yellow solid.
	With triethylamine;palladium diacetate; triphenylphosphine; at 70℃; under 4395.87 Torr;	Step A: Preparation of methyl 1-oxo-2,3-dihydro-1H-indene-5-carboxylate: 5-Bromo-2,3-dihydroinden-1-one (10 g, 48 mmol, 1 equiv.) and triethylamine (20 mL, 3 equiv.) were slurried in MeOH (100 mL) in a reaction bomb and the solution was degassed with Argon for 5 minutes. Pd(OAc)2 (0.54 g, 0.05 equiv.) and PPh3 (2.5 g, 0.2 equiv.) were added and the bomb was pressurized with CO to 85 psi and heated to 70 C. overnight. The reaction was cooled to room temperature and the volatiles were removed by rotary evaporation. The residue was taken up in EtOAc and 1N HCl, and the solids were filtered off solids through GF/F paper. The layers were separated and the organic layer was washed with saturated NaHCO3 and brine. The combined aqueous extracts were extracted with EtOAc and the combined organic extracts were dried over MgSO4, filtered, and concentrated to afford 10 g of the desires product as an off-white solid, which was carried on crude to the next step.

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 11039 - 11060
[2]Patent: WO2014/74422,2014,A1 .Location in patent: Paragraph 00201
[3]Patent: WO2017/218950,2017,A1 .Location in patent: Paragraph 00325
[4]Patent: US2007/49603,2007,A1 .Location in patent: Page/Page column 51

17
[ 91880-84-1 ]
[ 18107-18-1 ]
[ 68634-02-6 ]

Yield	Reaction Conditions	Operation in experiment
		To a suspension of 1-oxo-indan-5-carbonitrile (100 mg, 0.64 mmol) in KOH (25%, 0.21 mL) at 0 C., is added H2O2 (0.32 mL). The mixture is stirred at rt for 30 min, then at 50 C. for 1 h. After cooling to room temperature, the mixture is extracted with EtOAc (3×10 mL). The combined organic phases are washed with brine and dried over Na2SO4. Evaporation of the solvent affords 1-oxo-indan-5-carboxylic acid amide as a white solid. Aqueous HCl (4N, 3 mL) is added to the solid. The mixture is heated to 90 C. for 2 h. Then the reaction mixture is extracted with EtOAc (3×10 mL). The combined organic phasea are washed with brine. MeOH (5 mL) is added to the solution, followed by trimethylsilyldiazomethane (2M in ether) dropwise until all the carboxylic acid was consumed. Evaporation of solvent affords crude product, 1-oxo-indan-5-carboxylic acid methyl ester, which is pure enough for the next step. ESMS m/z 191.1 (M+H+).

Reference： [1]Patent: US2009/75996,2009,A1 .Location in patent: Page/Page column 21

18
(6-chloro-pyridin-3-yl)-imidazol-1-yl-methanone [ No CAS ]
[ 68634-02-6 ]
[ 760993-73-5 ]

Yield	Reaction Conditions	Operation in experiment
92%		Example 238A (2.7 g, 14.2 mmol) in 45 ML of THF was treated with NaH (60%, 1.14 g, 28.4 MMOL). After the addition of Example 230A (7.4 g, 35.5 mmol), the reaction mixture was stirred overnight and poured into ice water. The resulting mixture was acidified with concentrated HCl. Yellow solid was collected by filtration, washed with water and hot ethanol. The title product (4.3 g) was obtained at 92% yield. MS (DCI/NH3) m/z : 330.01 (M+H) +.

Reference： [1]Patent: WO2004/80973,2004,A1 .Location in patent: Page 186

19
[ 68634-02-6 ]
[ 613-94-5 ]
[ 1260116-74-2 ]

Reference： [1]Russian Chemical Bulletin,2010,vol. 59,p. 411 - 417

20
[ 68634-02-6 ]
[ 613-94-5 ]
[ 1260116-91-3 ]

Reference： [1]Russian Chemical Bulletin,2010,vol. 59,p. 411 - 417

21
[ 1407500-62-2 ]
[ 68634-02-6 ]
[ 1407501-70-5 ]

Yield	Reaction Conditions	Operation in experiment
39%		Step 1: A solution of 4-methyl-6-(thiazol-5-yl)-N-(4-(trifluoromethyl)pyridin-2- yl)pyridin-2-amine (1.5 g, 4.46 mmol) in THF (35.7 mL) was cooled to -78 C. LDA (2M, 6.69 mL, 13.38 mmol) solution was slowly added, and the resulting mixture was stirred as at -78 C for 30 minutes. In a separate dry flask, methyl l-oxo-2,3-dihydro-lH-indene-5-carboxylate (1.06 g, 5.57 mmol) was dissolved in THF (5 mL), then this solution was added to the reaction mixture, which was then allowed to warm to rt over a period of 3 hrs, then stirred at rt for an additional 13 h. The reaction was quenched by addition of 2 mL MeOH and then loaded directly onto a silica gel chromatography column and purified with a gradient solvent system of 0-100% EtOAc/hexanes. The product-containing fractions were evaporated to give methyl 1 -hydroxy- 1- (5-(4-methyl-6-((4-(trifluoromethyl)py^lH-indene-5-carboxylate 16C (912 mg, 39%) as a light yellow solid. MS ESI calcd forC26H2,F3N403S [M + H]+ 527, found 527.

Reference： [1]Patent: WO2012/151137,2012,A1 .Location in patent: Page/Page column 81

22
[ 1407500-62-2 ]
[ 68634-02-6 ]
[ 1407501-71-6 ]

Reference： [1]Patent: WO2012/151137,2012,A1

23
[ 6298-96-0 ]
[ 68634-02-6 ]
[ 1415502-43-0 ]

Yield	Reaction Conditions	Operation in experiment
452 mg		Preparation Example 174 To 713 mg of methyl 1-oxoindane-5-carboxylate were added 612 mg of (1S)-1-(4-methoxyphenyl)ethanamine, 0.23 ml of acetic acid, 600 mg of Molecular Sieves 4A, and 12 ml of toluene, followed by heating to reflux using a Dean-Stark type reflux device for 4 hours under reduced pressure (213 mbar). Then, 0.23 ml of acetic acid and 300 mg of Molecular Sieves 4A were added thereto, followed by heating to reflux using a Dean-Stark type reflux device for 4 hours under reduced pressure (213 mbar). The insoluble material was removed by filtration and the solvent was then evaporated under reduced pressure to obtain an intermediate product. To a solution of the obtained intermediate product in 13 ml of ethanol was added 161 mg of sodium borohydride under ice-cooling, followed by stirring for 1 hour under ice-cooling. The solvent was evaporated under reduced pressure, and to the obtained residue were added water, a saturated aqueous sodium hydrogen carbonate solution, and ethyl acetate to carry out a layer separation operation. The organic layer was washed with water and saturated brine in this order, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 452 mg of methyl (1S)-1-[(1S)-1-(4-methoxyphenyl)ethyl]amino}indane-5-carboxylate.

Reference： [1]Patent: US2014/88080,2014,A1 .Location in patent: Paragraph 0348

24
[ 68634-02-6 ]
[ 903557-36-8 ]

Reference： [1]Patent: US2014/88080,2014,A1

25
[ 68634-02-6 ]
[ 1609947-99-0 ]

Reference： [1]Patent: WO2014/74422,2014,A1

26
[ 68634-02-6 ]
[ 1609947-97-8 ]

Reference： [1]Patent: WO2014/74422,2014,A1

27
[ 68634-02-6 ]
(R)-methyl 1-(5-(6-amino-4-methylpyridin-2-yl)thiazol-2-yl)-1-hydroxy-2,3-dihydro-1H-indene-5-carboxylate [ No CAS ]

Reference： [1]Patent: WO2014/74422,2014,A1

28
[ 68634-02-6 ]
(R)-methyl 1-hydroxy-1-(5-(4-methyl-6-((4-methylpyridin-2-yl)amino)pyridin-2-yl)thiazol-2-yl)-2,3-dihydro-1H-indene-5-carboxylate [ No CAS ]

Reference： [1]Patent: WO2014/74422,2014,A1

29
[ 288-47-1 ]
[ 68634-02-6 ]
[ 1609947-95-6 ]