[ CAS No. 27404-31-5 ] {[proInfo.proName]}

Name: 27404-31-5|2-(Benzofuran-3-yl)ethanamine|96%
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SKU: A176453
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Quality Control of [ 27404-31-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 27404-31-5 ]

CAS No. :	27404-31-5	MDL No. :	MFCD08271905
Formula :	C₁₀H₁₁NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NEHYFMQXSNIAMZ-UHFFFAOYSA-N
M.W :	161.20	Pubchem ID :	12420812
Synonyms :

Calculated chemistry of [ 27404-31-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.2
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.69
TPSA :	39.16 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) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.0
Log Po/w (XLOGP3) :	1.64
Log Po/w (WLOGP) :	1.93
Log Po/w (MLOGP) :	1.26
Log Po/w (SILICOS-IT) :	2.33
Consensus Log Po/w :	1.83

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.3
Solubility :	0.816 mg/ml ; 0.00506 mol/l
Class :	Soluble
Log S (Ali) :	-2.08
Solubility :	1.36 mg/ml ; 0.00841 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.73
Solubility :	0.0303 mg/ml ; 0.000188 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.44

Safety of [ 27404-31-5 ]

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 [ 27404-31-5 ]

* 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.

Upstream synthesis route of [ 27404-31-5 ]
Downstream synthetic route of [ 27404-31-5 ]

[ 27404-31-5 ] Synthesis Path-Upstream 1~11

1
[ 52407-43-9 ]
[ 27404-31-5 ]

Reference： [1] Patent: US4835276, 1989, A,
[2] Journal of Medicinal Chemistry, 1985, vol. 28, # 12, p. 1756 - 1759
[3] Pharmacy and Pharmacology Communications, 1999, vol. 5, # 3, p. 177 - 181
[4] Patent: US4916223, 1990, A,
[5] Patent: US4686226, 1987, A,
[6] Patent: US4673680, 1987, A,
[7] Patent: US4710504, 1987, A,
[8] Patent: US4831035, 1989, A,
[9] Patent: US4690928, 1987, A,
[10] Patent: US2005/54634, 2005, A1,

2
[ 7169-34-8 ]
[ 27404-31-5 ]

Reference： [1] Pharmacy and Pharmacology Communications, 1999, vol. 5, # 3, p. 177 - 181
[2] Journal of Medicinal Chemistry, 1985, vol. 28, # 12, p. 1756 - 1759

3
[ 118-93-4 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

4
[ 63815-27-0 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

5
[ 1878-62-2 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

6
[ 21535-97-7 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

7
[ 4687-25-6 ]
[ 21535-97-7 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

8
[ 4687-23-4 ]
[ 21535-97-7 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

9
[ 67713-99-9 ]
[ 21535-97-7 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

10
[ 1023290-69-8 ]
[ 21535-97-7 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

11
[ 441055-15-8 ]
[ 21535-97-7 ]
[ 27404-31-5 ]
[ 24673-56-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 31, p. 9021 - 9024[2] Angew. Chem., 2015, vol. 127, p. 9149 - 9152,4

[ 27404-31-5 ] Synthesis Path-Downstream 1~67

1
[ 27404-31-5 ]
[ 108-24-7 ]
[ 67714-01-6 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1963,vol. 13,p. 819 - 821

2
[ 52407-43-9 ]
[ 27404-31-5 ]

Yield	Reaction Conditions	Operation in experiment
71%	aluminum nickel; In methanol;	Step B: Preparation of 2-(3-benzo[b]furanyl)ethylamine STR9 To a solution of 3.1 g of 3-cyanomethylbenzo[b]furan in 40 mL of methanol was added 2.4 g of Raney nickel. The reaction was agitated at 25 C. in a Parr apparatus under 40 psi hydrogen for 21/2 hours. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 2.2 g (71% yield) of oily product.
	In diethyl ether; water;	Step B: Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 grams (0.025 mole) of 3-cyanomethylbenzo[b]furan in 200 milliliters of diethyl ether was slowly added to a refluxing suspension of 3.84 grams (0.1 mole) of lithium aluminum hydride in 400 milliliters of ether and the mixture was heated 3 hours, then cooled and water was slowly added. The suspension was filtered and the filtrate was evaporated to obtain an oily product, the hydrochloride salt of which has m.p. 183-185 C.
	In diethyl ether; water;	Step B: Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 g (0.025 mole) of 3-cyanomethylbenzo[b]furan in 200 mL of diethyl ether was slowly added to a refluxing suspension of 3.84 g (0.1 mole) of lithium aluminum hydride in 400 mL of ether. The reaction was heated 3 hrs., cooled and water was slowly added. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 3.2 g of oily product. The hydrochloride salt has m.p. 183-185 C.

	In diethyl ether; water;	Step B: Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 g (0.025 mole) of 3-cyanomethylbenzo[b]furan in 200 mL of diethyl ether was slowly added to a refluxing suspension of 3.84 g (0.1 mole) of lithium aluminum hydride in 400 mL of ether. The reaction was heated 3 hours., cooled and water was slowly added. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 3.2 g of oily product. The hydrochloride salt has m.p. 183-185 C.
	In diethyl ether; water;	Step B Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 grams (0.025 mole) of 3-cyanomethylbenzo[b]furan in 200 milliliters of diethyl ether was slowly added to a refluxing suspension of 3.84 grams (0.1 mole) of lithium aluminum hydride in 400 milliliters of ether and the mixture was heated 3 hours, then cooled and water was slowly added. The suspension was filtered and the filtrate was evaporated to obtain an oily product, the hydrochloride salt of which has m.p. 183-185 C.
	In diethyl ether; water;	Step B Preparation of 2-(3-benzo[b]furanyl)ethylamine A solution of 3.97 g (0.025 mole) of 3-cyanomethylbenzo[b]furan in 200 mL of diethyl ether was slowly added to a refluxing suspension of 3.84 g (0.1 mole) of lithium aluminum hydride in 400 mL of ether. The reaction was heated 3 hours., cooled and water was slowly added. The suspension was filtered through a pad of filter aid and the filtrate was evaporated to give 3.2 g of oily product. The hydrochloride salt has m.p. 183-185 C.
		A. In a manner similar to that described in Step D of Example 32, but replacing 2-(1-tert-butoxycarbonyl indol-3-yl) propionitrile with 3-benzofuranylacetonitrile, the intermediate 3(2-aminoethyl) benzofuran was prepared; MS (ES): 162 (MH+).

Reference： [1]Patent: US4835276,1989,A
[2]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759
[3]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181
[4]Patent: US4916223,1990,A
[5]Patent: US4686226,1987,A
[6]Patent: US4710504,1987,A
[7]Patent: US4831035,1989,A
[8]Patent: US4690928,1987,A
[9]Patent: US2005/54634,2005,A1

3
[ 27404-31-5 ]
[ 109-94-4 ]
[ 100480-86-2 ]

Yield	Reaction Conditions	Operation in experiment
		Step C: Preparation of 3-(2-formamidoethyl)benzo[b]furan A solution of 2.35 grams (0.015 mole) of 2-(3-benzo[b]furanyl)ethylamine and 5 milliliters of ethyl formate was heated at 60 C. for 3 hours, poured into 2N HCl extracted with methylene chloride, the latter washed with 5% sodium hydroxide, dried, filtered and concentrated to obtain the product.
		Step C: Preparation of 3-(2-Formamidoethyl)benzo[b]furan A solution of 2.35 g (0.015 mole) of 2-(3-benzo[b]furanyl)ethylamine and 5 mL of ethyl formate was heated at 60 C. for 3 hours, poured into 2N HCl and washed with methylene chloride which in turn was washed with 5% sodium hydroxide (w/v), dried (MgSO4), filtered and concentrated to give 2.70 g of product.
		Step C: Preparation of 3-(2-Formamidoethyl)benzo[b]furan A solution of 2.35 g (0.015 mole) of 2-(3-benzo[b]furanyl)ethylamine and 5 mL of ethyl formate was heated at 60 C. for 3 hours, poured into 2 N HCl and washed with methylene chloride which in turn was washed with 5% sodium hydroxide (w/v), dried (MgSO4), filtered and concentrated to give 2.70 g of product.

		Step C Preparation of 3-(2-formamidoethyl)benzo[b]furan A solution of 2.35 grams (0.015 mole) of 2-(3-benzo[b]furanyl)ethylamine and 5 milliliters of ethyl formate was heated at 60 C. for 3 hours, poured into 2N HCl extracted with methylene chloride, the latter washed with 5% sodium hydroxide, dried, filtered and concentrated to obtain the product.
		Step C: Preparation of 3-(2-Formamidoethyl)benzo[b]furan STR10 A solution of 121 g of 2-(3-benzo[b]furanyl)-ethylamine and 300 mL of ethyl formate was heated at 60 C. for 3 hours, poured into 2N HCl and washed with methylene chloride which in turn was washed with 5% sodium hydroxide (w/v), dried (Na2 SO4), charcoaled and concentrated to give 118 g of product.
		Step C Preparation of 3-(2-Formamidoethyl)benzo-[b]furan A solution of 2.35 g (0.015 mole) of 2-(3benzo[b]furanyl)ethylamine and 5 mL of ethyl formate was heated at 60 C. for 3 hours, poured into 2N HCl and washed with methylene chloride which in turn was washed with 5% sodium hydroxide (w/v), dried (MgSO4), filtered and concentrated to give 2.70 g of product.

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759
[2]Patent: US4916223,1990,A
[3]Patent: US4686226,1987,A
[4]Patent: US4710504,1987,A
[5]Patent: US4831035,1989,A
[6]Patent: US4835276,1989,A
[7]Patent: US4690928,1987,A

Yield	Reaction Conditions	Operation in experiment
93%		The catalyst was filtered through a plug of Arbocel and the yellow-brown filtrate chromatographed using 0-5% MeOH in DCM to provide the title product (380 mg, 93%); 1H-NMR (400 MHz, CDCl3) delta: 1.20 (brs., 2H), 2.80 (t, 2H), 3.02 (t, 2H), 7.15-7.25 (m, 2H), 7.43 (dd, 2H), 7.55 (dd, 1H); LRMS: M+H, 162. (ES+).
		Preparation 131 2-(2,3-Dihydro-1-benzofuran-3-yl)-ethylamine The product from Preparation 130 (200 mg, 1.24 mmol) was mixed with ethanol (20 ml) and 20 mg of 10wt % Pd/C and hydrogenated at 40p.s.i. hydrogen pressure for 48 h. A further 20 mg of catalyst was added, and the whole hydrogenated at 60p.s.i. and 40 C. for a further 72 h.
		Step B: Preparation of 3-(2-aminoethyl)benzo[b]furan STR9 A solution of 3.1 g of nitrile 2 was treated with 2.4 g of Raney Nickel in 40 ml methanol at 40 PSI of hydrogen for 12 hours or until a theoretical amount of hydrogen was absorbed (2.0 equivalents). The catalyst was removed by filtration and the methanol was removed in vacuo to give 2.2 g (71%) yield of amine 3.

6
[ 27404-31-5 ]
[ 625-38-7 ]
N-[2-(benzo[b]furan-3-yl)ethyl]vinylacetamide [ No CAS ]

Reference： [1]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181

7
N-2-(benzo[b]furan-3-yl)ethylamine hydrochloride [ No CAS ]
[ 27404-31-5 ]

Reference： [1]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181

8
[ 27404-31-5 ]
[ 7560-50-1 ]
3-[4-[[[2-(3-benzofuranyl)ethyl]amino]methyl]phenyl]-(2E)-2-propenoic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4609 - 4624

9
[ 20697-04-5 ]
[ 27404-31-5 ]
2-(2-benzofuran-3-yl-ethylamino)-1-(3-chloro-phenyl)-ethanol [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 184 - 198

10
[ 27404-31-5 ]
[ 19351-63-4 ]
(4S,5R,6S)-4-[(S)-1-(1,2,3,4-Tetrahydro-benzo[4,5]furo[2,3-c]pyridin-1-yl)methyl]-6-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-5-vinyl-5,6-dihydro-4H-pyran-3-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2475 - 2478

11
[ 26726-16-9 ]
[ 27404-31-5 ]
[ 906344-96-5 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5432 - 5439

12
[ 27404-31-5 ]
[ 530-62-1 ]
[ 909708-04-9 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

13
[ 73746-79-9 ]
[ 27404-31-5 ]
C₁₆H₁₇NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 29; la-Methyl-1, 3,4, 5,6, 11b-hexahydro-2H-ll-oxa-4a-aza-benzola] fluoren-1- ol; To a solution of 0.48 g (3.0 mmol) of 2- (3-benzo [b] furanyl) ethylamine in 5.0 ml of xylene was added 0.34 g (3.0 mmol) of ot-methyl-o-valerolactone. The mixture was refluxed for 7.5 h. After evaporation of the solvent the residue was dissolved in 6.0 ml of toluene, 0.72 ml of freshly distilled phosphorus oxychloride was added and the reaction mixture was refluxed for 11 h. The solution was evaporated in vacuum and the obtained oil was mixed with a 20% solution of acetic acid (3 x 20 ml). The solid was filtered off and the aqueous solution was made alkaline (pH 11) with 25% ammonium hydroxide under cooling and extracted with dichloromethane (3 x 20 ml). To the combined organic phases was added 12.5 ml of 4 M sodium hydroxide and this mixture was refluxed for 1 h. The organic phase was dried over sodium sulfate, the drying agent was filtered off and the filtrate was concentrated to give the corresponding enamine, which was oxidised as described in example 9. NMR: 1.18 (s, 3H), 3.25 (br d, 1H), 7.10-7. 50 (m, 4H). MS: 257 (25%), 242 (10%), 172 (100%).

Reference： [1]Patent: WO2003/82866,2003,A1 .Location in patent: Page/Page column 40

14
[ 27404-31-5 ]
cis-1,2-cyclohexane dicarboxylic anhydride [ No CAS ]
C₁₈H₁₉NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 40; 5,6, 7, 7ap, 8,9, 10, 11, 11ap, 11ba-Decahydro-12-oxa-6a-aza-indeno [1, 2- a] fluorene; To a solution of 0.70 g (0.43 mmol) of 2- (3-benzo [b] furanyl) ethylamine in 30 ml of chlorobenzene was added 0.13 g (0.87 mmol) of cis-1, 2- cyclohexanedicarboxylic anhydride. The mixture was irradiated in a microwave oven (1000 W, T=130C) for 30 min. Chlorobenzene was replaced by ethanol (5 ml) and 82.7 mg (2.18 mmol) of sodium borohydride was added. The mixture was stirred at rt for 18 h, after which water was added and the product was isolated in the usual manner. Trifluoroacetic acid (0.12 ml, 1.53 mmol) in dichloromethane (10 ml) was added and the reaction mixture was stirred for 2 h at rt. Alkaline work-up (4 M sodium hydroxide), gave the amide intermediate, which was dissolved in diethyl ether (15 ml), 0.1 g (2.63 mmol) of lithium aluminum hydride was added and the reaction mixture was refluxed for 1.5 h. Water was slowly added under cooling. After normal extraction procedures, the crude product was purified by column chromatography (silica gel, dichloromethane/methanol, 90: 10). NMR: 1.77 (m, 2H), 2.07 (m, 1H), 2.29 (m, 1H), 2.48 (m, 1H), 3.04 (m, 1H), 3.20 (m, 1H), 4.13 (s, 1H), 7.18-7. 50 (m, 4H). MS: 267 (46%), 266 (100%), 185 (52%), 170 (12%).

Reference： [1]Patent: WO2003/82866,2003,A1 .Location in patent: Page/Page column 44

15
[ 27404-31-5 ]
[ 610783-13-6 ]
C₁₉H₂₄ClNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In dichloromethane; at 20℃; for 0.75h;	EXAMPLE 45; loc-Methyl-1, 3,4, 5,6, llboc-hexahydro-2H-11-oxa-4a-aza- benzo [a] fluorene-l-carboxylic acid ethyl ester; To a mixture of 0.375 g (2.33 mmol) of 2- (3-benzo [b] furanyl) ethylamine and triethylamine (0.97 ml, 7.0 mmol) in dichloromethane (3 ml) was added 0.56 g (2.33 mmol) 5-chloro-2-ethoxycarbonyl-2-methylvaleroyl chloride (prepared according to the process described for the corresponding 2-ethyl derivative in J Org. Cliem. 45 (1980) 32-34) in dichloromethane (4 ml). After stirring at rt for 45 min, water was added and the mixture was extracted with dichloromethane. Drying over sodium sulfate, filtration of the drying agent and evaporation of the solvent gave the crude amide, which was purified by column chromatography (ethyl acetate/heptane, 1: 1). The pure amide (0.3 g, 0.82 mmol) was dissolved in toluene (3 ml) and 0.38 ml (4.1 mmol) of phosphorus oxychloride was added. The mixture was refluxed for 2 h, after which it was evaporated to dryness. The residue was dissolved methanol (3 ml) and 57 mg (1.5 mmol) of sodium borohydride was added in portions. After stirring at rt for 1 h, water was added and the mixture was extracted with ethyl acetate. Drying over sodium sulfate, followed by filtration and evaporation gave the crude ester which was purified by column chromatography (silica gel, ethyl acetate/heptane, 1: 1). NMR : 0.65 (t, 3H), 1.55 (s, 3H), 3.30 (br s, 1H), 7.16-7. 50 (m, 4H). MS: 313 (70%), 312 (100%), 284 (22%), 240 (32%), 198 (80%), 171 (35%), 170 (95%).

Reference： [1]Patent: WO2003/82866,2003,A1 .Location in patent: Page/Page column 46

16
[ 27404-31-5 ]
[ 909708-06-1 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

17
[ 27404-31-5 ]
[ 909708-05-0 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

18
[ 27404-31-5 ]
[ 909708-07-2 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

19
[ 27404-31-5 ]
C₁₉H₁₉NO₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

20
[ 27404-31-5 ]
[ 909708-18-5 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

21
[ 27404-31-5 ]
C₂₁H₂₃NO₅ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 10589 - 10595

22
[ 27404-31-5 ]
3-(2-benzofuran-3-yl-ethyl)-7-bromo-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]-dec-8-en-2-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5432 - 5439

23
[ 27404-31-5 ]
[ 913169-58-1 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5432 - 5439

24
[ 27404-31-5 ]
3-(2-benzofuran-3-yl-ethyl)-7-bromo-6,6-dimethyl-10-oxa-3-aza-tricyclo[5.2.1.0^1,5]-dec-8-en-2-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 5432 - 5439

25
[ 27404-31-5 ]
N-hydroxy-3-[4-[[[2-(benzofuran-3-yl)-ethyl]-amino]methyl]phenyl]-(2E)-2-propenamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2003,vol. 46,p. 4609 - 4624

26
[ 7169-34-8 ]
[ 27404-31-5 ]

Reference： [1]Pharmacy and Pharmacology Communications,1999,vol. 5,p. 177 - 181
[2]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759

27
[ 27404-31-5 ]
[ 97456-65-0 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759

28
[ 27404-31-5 ]
[ 98678-87-6 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759

29
[ 27404-31-5 ]
[ 100480-87-3 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759

30
[ 27404-31-5 ]
[ 98678-88-7 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759

31
[ 27404-31-5 ]
[ 98678-89-8 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1756 - 1759

32
[ 27404-31-5 ]
[ 65619-20-7 ]
1,1-(3-dimethylamino-3-phenyl-pentamethylen)-1,2,3,4-tetrahydro-benzo[4,5]furo[2,3-c]pyridine [ No CAS ]

Reference： [1]Patent: WO2004/43967,2004,A1 .Location in patent: Page/Page column 56

33
[ 27404-31-5 ]
[ 629662-33-5 ]

Yield	Reaction Conditions	Operation in experiment
		B. In a manner similar to that described in Step E of Example 32, but replacing 2-(1H-indol-3-yl)propylamine with 3(2-aminoethyl) benzofuran, the intermediate 6,7-dihydro-5H-10-oxa-7-azabenzo[a]azulene-9-carboxylic acid ethyl ester was prepared; MS (ES): 258 (MH+).

Reference： [1]Patent: US2005/54634,2005,A1

34
[ 50-00-0 ]
[ 27404-31-5 ]
[ 106792-29-4 ]

Yield	Reaction Conditions	Operation in experiment
		13. 1 -(4-CYCLOBUTYL-PIPERAZIN- 1 - YL)-2 -(3 ,4-DIHYDRO- 1 H- BENZO[4,5]FURO[2,3-C]PYRIDIN-2 -YL)-ETHANONE (SCHEME 11); Step 1. l,2,3,4-Tetrahydro-benzo[4,5]furo[2,3-c]pyridine; <n="68"/>To a solution of 2-benzofuran-3-yl-ethylamine (510 g, 23.16mmol) in formic acid (3 mL) at rt is added paraformaldehyde (104 mg, 3.17 mmol, 1.1 eq.). The mixture is stirred at 500C for 3 h. Formic acid is evaporated. The residue is dissolved in DCM (10 mL) and washed with 2.0 N aqueous NaOH solution. The aqueous layer is extracted with DCM twice (2 x 5 mL). The combined organics are dried over sodium sulfate. The solvent is removed under reduced pressure to yield a residue which is purified through chromatography eluting with DCM/MeOH (90:10) to give the title compound. MS (+VE) m/z 174.1 (M+ +1).

Reference： [1]Patent: WO2009/3003,2008,A2 .Location in patent: Page/Page column 66-67

35
[ 27404-31-5 ]
[ 108-59-8 ]
[ 1226974-80-6 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 499 - 518

36
[ 27404-31-5 ]
[ 105-53-3 ]
[ 1226974-85-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 499 - 518

37
[ 27404-31-5 ]
[ 1258503-51-3 ]
[ 1258502-33-8 ]

Yield	Reaction Conditions	Operation in experiment
9%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	EXAMPLE 91 - PREPARATION OF Lambda/-(2-(benzofuran-3-yl)ethyl)-5-(3- fluorobenzyl)isoxazole-3-carboxamide.; A solution of the 5-(3-fluorobenzyl)isoxazole-3-carboxylic acid (0.057 g, 0.257 mmol), 2- (benzofuran-3-yl)ethanamine (0.042 g; 0.260 mmol), HATU (0.108 g; 0.285 mmol) and N,N-diisoprpylethylamine (0.1 12 mL; 0.649 mmol) in DMF (3 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified by preparative HPLC (method 2) to yield 0.008 g (9%) of the title compound as a white solid. ESI/APCI(+):365 (M+H). ESI/APCI(+):363 (M-H).

Reference： [1]Patent: WO2010/142801,2010,A1 .Location in patent: Page/Page column 236

38
[ 943818-65-3 ]
[ 27404-31-5 ]
[ 1355024-76-8 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 844 - 847

39
[ 943818-65-3 ]
[ 27404-31-5 ]
[ 1355024-57-5 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 844 - 847

40
[ 27404-31-5 ]
[ 778531-36-5 ]
[ 1571-08-0 ]
[ 1569976-46-0 ]

Reference： [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 2334 - 2356

41
[ 27404-31-5 ]
[ 99-61-6 ]
[ 76-05-1 ]
1-(3-nitrophenyl)-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	In dichloromethane; at 0℃; for 38.16h;Reflux;	Preparation of 1-(3-nitrophenyl)-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine (5). [0042] 3-Nitrobenzaldehyde (111.8 mg, 0.74 mmol) and <strong>[27404-31-5]2-(benzofuran-3-yl)ethanamine</strong> (119.3 mg, 0.74 mmol) were dissolved in anhydrous dichloromethane (5 mL). The mixture was cooled to 0C before trifluoroacetic acid (73.4 muL, 0.96 mmol) was slowly added via syringe. The mixture was stirred for 10 min at 0C, and then refluxed for 14 h. For completion of the reaction, extra trifluoroacetic acid (76.5 muL, 1.0 mmol) was added and the mixture was further refluxed for 24 h. Solvent was removed under reduced pressure. The resulting residue was triturated in diethyl ether (15 mL), filtered and dried to yield the TFA salt of 5 as a brown solid (105 mg, 48%). [0044] 1H RMN (400 MHz, CDCl3) delta 3.04-3.17 (m, 2H), 3.48-3.60 (m, 2H), 6.28 (s, 1H), 7.36-7.38 (m, 2H), 7.56-7.58 (m, 1H), 7.73-7.75 (m, 1H), 7.79-7.86 (m, 2H), 8.38-8.40 (m, 2H), 9.88 (bs, 1H), 10.15 (bs, 1H). [0045] 13C RMN (100 MHz, CDCl3) delta 7.9, 54.4, 111.6, 113.9, 120.0, 123.5, 124.8, 125.1, 125.4, 126.3, 130.7, 134.7, 136.4, 145.5, 147.9, 154.4. [0046] HPLC: tR = 5.75 min. [0047] MS: m/z 295 ([M+H]+).

Reference： [1]Patent: EP2738173,2014,A1 .Location in patent: Paragraph 0042; 0043; 0044; 0045; 0046; 0047

42
[ 27404-31-5 ]
[ 99-61-6 ]
[ 76-05-1 ]
1-(3-nitrophenyl)-1,2,3,4-tetrahydro[1]benzofuro[2,3-c]pyridine trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	In dichloromethane; at 0℃; for 38h;Reflux;	3-Nitrobenzaldehyde (1 1.8 mg, 0.74 mmol) and 2-(benzofuran~3~yl)ethanamine (119.3 mg, 0.74 mmol) were dissolved in anhydrous dichlororaethane (5 mL). The mixture was cooled to 0C before trifluoroacetic acid (73.4 0.96 mmol) was slowly added via syringe. The mixture was stirred for 10 min at 0C, and then refluxed for 14 h. For completion of the reaction, extra trifluoroacetic acid (76.5 mu,, 1.0 mmol) was added and the mixture was further refluxed for 24 h. Solvent was removed under reduced pressure. The resulting residue was triturated in diethyl ether (15 mL), filtered and dried to yield the TFA salt of 5 as a brown solid (105 mg, 48%).

Reference： [1]Patent: WO2014/83529,2014,A1 .Location in patent: Page/Page column 13; 14

43
[ 4687-25-6 ]
[ 21535-97-7 ]
[ 27404-31-5 ]
[ 24673-56-1 ]