3373-00-0|6-Hydroxy-1,2,3,4-tetrahydroquinoline| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 3373-00-0 ] Purity: 95% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 3373-00-0 ]

CAS No. :	3373-00-0
Formula :	C₉H₁₁NO
M.W :	149.19
SMILES Code :	C1=C(O)C=CC2=C1CCCN2
MDL No. :	MFCD00800243
InChI Key :	CTJSPUFGQNVJJP-UHFFFAOYSA-N
Pubchem ID :	76897

Safety of [ 3373-00-0 ]

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

Computational Chemistry of [ 3373-00-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.33
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	2.0
Molar Refractivity	48.36
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	32.26 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.52
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.93
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.18
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.4
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.97
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.6

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.38
Solubility	0.615 mg/ml ; 0.00413 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.23
Solubility	0.876 mg/ml ; 0.00587 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.68
Solubility	0.309 mg/ml ; 0.00207 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.84 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.45

Application In Synthesis of [ 3373-00-0 ]

* 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 [ 3373-00-0 ]

[ 3373-00-0 ] Synthesis Path-Downstream 1~38

1
[ 580-16-5 ]
[ 3373-00-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium(IV) oxide; In methanol;	The starting material was prepared as follows: 6-Hydroxyquinoline (1 g, 6.9 mmol) was dissolved in methanol and hydrogenated at 3 atmospheres pressure with platinum(IV) oxide (276 mg) over 24 hours. The catalyst was removed by filtration over a pad of celite and the solvent was evaporated. The solid was washed with ether to give 6-hydroxy-(1,2,3,4)-tetrahydroquinoline (698 mg, 68 %). 1H NMR Spectrum (DMSOd6) 1.75 (m, 2H); 2.60 (m, 2H); 3.05 (m, 2H); 4.90 (br s, 1H); 6.30 (m, 3H); 8.25 (br s, 1H)

References: [1]Chemistry - A European Journal,2016,vol. 22,p. 17151 - 17155.
[2]ChemCatChem,2017,vol. 9,p. 2496 - 2505.
[3]Organic and biomolecular chemistry,2020,vol. 18,p. 1214 - 1220.
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 3216 - 3220.
    Angew. Chem.,2017,vol. 129,p. 3264 - 3268,5.
[5]Catalysis science and technology,2017,vol. 7,p. 1981 - 1985.
[6]Patent: DE42871, .
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 1,p. 181.
[7]Journal of the American Chemical Society,1944,vol. 66,p. 1166,1168.
[8]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1939,vol. 59,p. 478,480; dtsch. Ref. S. 222.
    Chem.Abstr.,1939,p. 9306.
[9]Helvetica Chimica Acta,1949,vol. 32,p. 1278,1281.
[10]Journal of the Chemical Society. Perkin transactions I,1980,p. 1933 - 1939.
[11]Patent: EP1154774,2005,B1 .Location in patent: Page/Page column 118.
[12]Tetrahedron Letters,2016,vol. 57,p. 329 - 332.
[13]Journal of the American Chemical Society,2017,vol. 139,p. 9419 - 9422.

2
[ 3373-00-0 ]
[ 98-88-4 ]
[ 855871-84-0 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1939,vol. 59,p. 478,480; dtsch. Ref. S. 222.
Chem.Abstr.,1939,p. 9306.

Yield	Reaction Conditions	Operation in experiment
		1.9 In analogy to example 1.8, 6-(5-Bromo-pentyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester and N-allylmethylamine were converted to yield 6-[5-(Allyl-methyl-amino)-pentyloxy]-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester as colorless oil, MS: 443 (MH+, 1Cl).

5
[ 580-16-5 ]
[ 7664-93-9 ]
[ 7732-18-5 ]
[ 3373-00-0 ]

References: [1]Helvetica Chimica Acta,1949,vol. 32,p. 1278,1281.

6
[ 580-16-5 ]
[ 7732-18-5 ]
KOH-solution [ No CAS ]
[ 3373-00-0 ]

References: [1]Helvetica Chimica Acta,1949,vol. 32,p. 1278,1281.

7
[ 3373-00-0 ]
[ 24424-99-5 ]
[ 327044-56-4 ]

Yield	Reaction Conditions	Operation in experiment
76.7%	With sodium hydroxide; In 1,4-dioxane; water; at 20℃;	Procedure E: 1, 2,3, 4-tetrahydro-quinolin-6-ol (CAS Registry Number 3373-00-0) (25 g, 172.9 mmol) is treated with di-tert-butyl dicarbonate (56.6 g, 259.4 mmol) in a solvent mixture of dioxane (200 mL) and 1N [NAOH] (200 [ML),] and reaction mixture allowed to stir at room temperature overnight. The layers are separated, and the aqueous layer is washed with ethyl acetate (2X). The organic layers are combined and washed with brine [(1X),] dried over [NA2S04] and the organic layer evaporated to give a crude oil. Flash chromatography (Biotage, 10% EtOAc/hexanes) gives the desired material (33.0 g, 76.7% yld).
	With triethylamine; for 2.0h;Heating / reflux;Product distribution / selectivity;	6-Hydroxy-l,2,3,4-tetrahydro quinoline (1 eq), Boc anhydride (1.2 eq) and triethyl amine (1.2 eq) were mixed and heated to refluxed for 2hr. Mixture was quenched in water and product was extracted with EtOAc to afford title compound as oil.Compound was used directly for the next reaction without purification.

References: [1]Patent: WO2004/26837,2004,A2 .Location in patent: Page 17-18.
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3415 - 3418.
[3]Patent: WO2009/87649,2009,A1 .Location in patent: Page/Page column 25; 26.

8
[ 120-15-0 ]
[ 3373-00-0 ]

Yield	Reaction Conditions	Operation in experiment
71.11%	With boron tribromide; In dichloromethane; at 0 - 15℃; for 2.0h;	Compound 26A (3.00 g, 18.38 mmol) was dissolved in 50 ml of dichloromethane, BBr3 (13.81 g, 55.14 mmol)was added at 0 C, and then stirred at 15 C for 2 hours. The reaction solution was concentrated and the reaction wasquenched by 5 ml of methanol. Saturated sodium bicarbonate solution (20 ml) was added and stirred for 30 min, thenextracted with 20 ml of ethyl acetate three times. The organic phases were combined and dried over anhydrous sodiumsulfate and concentrated to give a crude product. The crude product was purified by silica gel column chromatography(petroleum ether/ethyl acetate was from 3:1 to 1:1) to give compound 26B (1.95 g, the yield was 71.11%).1H NMR (400 MHz, DMSO-d6) 8.24 (s, 1H), 6.22-6.35 (m, 3H), 4.93 (br. s., 1H), 3.02-3.10 (m, 2H), 2.57 (t, J = 6.4 Hz,2H), 1.67-1.80 (m, 2H).

References: [1]Patent: EP3293177,2018,A1 .Location in patent: Paragraph 0222; 0224.
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3415 - 3418.

9
[ 5263-87-6 ]
[ 3373-00-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3415 - 3418.
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 1933 - 1939.
[3]Patent: EP3293177,2018,A1 .

10
[ 3373-00-0 ]
1-ethyl-6-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-quinoline [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3415 - 3418.

11
[ 3373-00-0 ]
[6-(3-piperidin-1-yl-propoxy)-3,4-dihydro-2<i>H</i>-quinolin-1-yl]-thiophen-2-yl-methanone [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3415 - 3418.

12
[ 3373-00-0 ]
[ 676254-99-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3415 - 3418.

13
[ 3373-00-0 ]
[ 676255-04-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3415 - 3418.

14
[ 3373-00-0 ]
[ 754977-12-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3415 - 3418.

15
[ 3373-00-0 ]
6-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-quinoline dihydrochloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3415 - 3418.

16
[ 104-94-9 ]
optically inactive bis-<2-chloro-propyl>-<2>naphthyl-amine [ No CAS ]
[ 3373-00-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1933 - 1939.

17
[ 3373-00-0 ]
[ 873970-10-6 ]

18
[ 3373-00-0 ]
1-cyclohexanecarbonyl-6-methoxy-1,2,3,4-tetrahydro-quinoline [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1939,vol. 59,p. 478,480; dtsch. Ref. S. 222.
    Chem.Abstr.,1939,p. 9306.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1939,vol. 59,p. 478,480; dtsch. Ref. S. 222.
    Chem.Abstr.,1939,p. 9306.
[3]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1939,vol. 59,p. 478,480; dtsch. Ref. S. 222.
    Chem.Abstr.,1939,p. 9306.

19
[ 3373-00-0 ]
[ 24223-33-4 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1939,vol. 59,p. 478,480; dtsch. Ref. S. 222.
Chem.Abstr.,1939,p. 9306.

20
[ 3373-00-0 ]
[ 855871-82-8 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1939,vol. 59,p. 478,480; dtsch. Ref. S. 222.
Chem.Abstr.,1939,p. 9306.

21
[ 3373-00-0 ]
[ 1538-75-6 ]
6-hydroxy-4-(1-tertbutoxycarbonyl)-1,2,3,4-tetrahydroquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	6-Hydroxy-(1,2,3,4)-tetrahydroquinoline (250 mg, 1.7 mmol) was suspended in acetone (1 ml) and trichloromethane (1 ml) under argon. Tert-Butoxycarbonylanhydride (365 mg, 1.7 mmol) in solution in acetone was added dropwise followed by THF (2ml) to help the solubilisation. The reaction mixture was stirred overnight at ambient temperature, the solvent was evaporated, the residue was partitioned between ethyl acetate and water, the organic phase was washed with water, brine, dried (MgSO4), filtered and the solvent evaporated. The resulting gum was purified by flash chromatography using dichloromethane/methanol (97/3) as solvent. Evaporation of the solvent gave 6-hydroxy-4-(1-tertbutoxycarbonyl-1,2,3,4-tetrahydroquinoline (344 mg, 82%) as a brown foam 1H NMR Spectrum: (DMSOd6) 1.50 (m, 9H); 1.90 (m, 2H); 2.70 (t, 2H); 3.65 (t, 2H); 4.75 (br s, 1H); 6.55 (d, 1H); 6.65 (dd, 1H); 7.45 (d, 1H)

References: [1]Patent: EP1154774,2005,B1 .Location in patent: Page/Page column 118.

22
[ 3373-00-0 ]
[ 7440-44-0 ]
[ 76-02-8 ]
[ 62265-74-1 ]

Yield	Reaction Conditions	Operation in experiment
	With calcium carbonate; In chloroform; water;	A-9. 1,2,3,4-Tetrahydro-1-(trichloroacetyl)-6-quinolinol -- A stirred mixture containing 15.0 g. of <strong>[3373-00-0]1,2,3,4-tetrahydro-6-quinolinol</strong> in 250 ml. of dry chloroform, 10.0 g. of calcium carbonate and 18.0 g. of trichloroacetyl chloride was refluxed for about 24 hours. To the reaction mixture was added another 9 g. (5 ml.) of trichloroacetyl chloride and the mixture was refluxed with stirring for an additional three hours, allowed to cool to room temperature and then poured into 200 ml. of water. The mixture was brought to a pH of about 7 with solid sodium bicarbonate. The chloroform layer was separated and the aqueous layer was extracted with three 400 ml. portions of benzene. The benzene extracts and the chloroform layer were combined and washed with 5% aqueous sodium bicarbonate until the wash water remained basic. The benzene-chloroform solution was dried over anhydrous sodium sulfate and the solvents removed in vacuo. The remaining residue was recrystallized twice from methylene dichloride, the second time using decolorizing charcoal, and the resulting product was dried at 40 C. and 50 mm. to yield 9.25 g. of 1,2,3,4-tetrahydro-1-(trichloroacetyl)-6-quinolinol, m.p. 153-155 C.

References: [1]Patent: US3997542,1976,A .

23
[ 79-36-7 ]
[ 3373-00-0 ]
[ 107-06-2 ]
[ 62265-67-2 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; chloroform;	A-1. 1-(Dichloroacetyl)-<strong>[3373-00-0]1,2,3,4-tetrahydro-6-quinolinol</strong> -- To a stirred mixture containing 14.9 g. of <strong>[3373-00-0]1,2,3,4-tetrahydro-6-quinolinol</strong> and 250 ml. of dry ethylene dichloride was added dropwise 16.2 g. of dichloroacetyl chloride and the resulting reaction mixture was stirred on a steam bath for fourteen hours. The reaction mixture was heated in vacuo to remove the ethylene dichloride. The remaining material was taken up in chloroform and the chloroform removed in vacuo to yield 28 g. of powder. The powder was slurried at room temperature with 100 ml. of n-hexane containing 10 ml. of isopropyl alcohol and the remaining solid, 24.5 g., was recrystallized twice from chloroform-n-hexane and dried at 60 C. and 0.1 mm. for seven hours to yield 10.5 g. of 1-(dichloroacetyl)-<strong>[3373-00-0]1,2,3,4-tetrahydro-6-quinolinol</strong>, m.p. 136-136.5 C.

References: [1]Patent: US3997542,1976,A .

24
[ 3373-00-0 ]
[ 79-04-9 ]
[ 62265-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In chloroform;	A-8. 1-Chloroacetyl)-<strong>[3373-00-0]1,2,3,4-tetrahydro-6-quinolinol</strong> -- A stirred mixture containing 15.0 g. of <strong>[3373-00-0]1,2,3,4-tetrahydro-6-quinolinol</strong> in 250 ml. of dry chloroform, 7.5 g. of sodium carbonate and 12.5 g. of chloroacetyl chloride was refluxed for about sixteen hours and filtered while hot. The collected solids were recrystallized from acetonitrile to yield 14.9 g. of 1-(chloroacetyl)-<strong>[3373-00-0]1,2,3,4-tetrahydro-6-quinolinol</strong>, m.p. 146.5-150 C.

References: [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 11385 - 11389.
Angew. Chem.,2019,vol. 131,p. 11507 - 11511,5.
[2]Patent: US3997542,1976,A .

25
[ 108-30-5 ]
[ 3373-00-0 ]
[ 957203-97-3 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃; for 17.0h;	To a THF solution (30 mL) of <strong>[3373-00-0]6-hydroxy-1,2,3,4-tetrahydroquinoline</strong> (2.00 g), succinic anhydride (1.34 g) was added, and the mixture was stirred for 17 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in dichloromethane, followed by extraction with 1N aqueous sodium hydroxide solution. The extracts were combined, and the pH of the combined extract was adjusted to 2 by use of 10% aqueous hydrochloric acid solution, followed by extraction with ethyl acetate. The extract was washed with saturated brine and dried over sodium sulfate anhydrate. Sodium sulfate anhydrate was removed by filtration, and the filtrate was concentrated under reduced pressure, to thereby yield the title compound (2.25 g). NMR(DMSO-d6)delta: 1.81(2H,t,J=7.1Hz),2.33-2.75(5H,m),3.27-3.40(1H,m),3.62(1H,t,J=6.4Hz),6.577(3H,s),7.12(1H,s),9.29(1H,s ),12.05(1H,s). MS(ESI)m/z:250(M+H)+.

References: [1]Patent: EP2017263,2009,A1 .Location in patent: Page/Page column 43-44.

26
[ 3934-20-1 ]
[ 3373-00-0 ]
[ 1228447-10-6 ]

Yield	Reaction Conditions	Operation in experiment
> 80%	With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 80℃;	Example 5: Synthesis of Pyrintegrin Derivatives; [0212] To a mixture of 2,4-dichloropyrimidine 4 (1.0 eq.), R1NH2 (1.2 eq.) and diisopropylethylamine (1.2 eq.) in n-butanol was heated at 80 0C overnight. The solvent was evaporated, and the residue was purified by flash column chromatography to intermediate 10 in excellent yield (> 80%), which was then treated with R2NH2 (1.2 eq.) in DMF was added /?-toluenesulfonic acid (2 M in dioxane) (1.2 eq.). The reaction mixture was stirred at 90 0C overnight, and then purified directly by preparative HPLC to give Pyrintegrin derivatives 11 in excellent yields.

References: [1]Patent: WO2010/65721,2010,A1 .Location in patent: Page/Page column 59.

27
[ 3373-00-0 ]
[ 96557-30-1 ]
C₁₇H₁₈BrNO [ No CAS ]