[ CAS No. 4244-66-0 ] {[proInfo.proName]}

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Quality Control of [ 4244-66-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 4244-66-0 ]

Product Details of [ 4244-66-0 ]

CAS No. :	4244-66-0	MDL No. :	MFCD23098720
Formula :	C₁₀H₁₁ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	198.65	Pubchem ID :	-
Synonyms :

Safety of [ 4244-66-0 ]

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Application In Synthesis of [ 4244-66-0 ]

* 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 [ 4244-66-0 ]

[ 4244-66-0 ] Synthesis Path-Downstream 1~14

1
[ 27912-85-2 ]
[ 4244-66-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With oxalyl dichloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere; Cooling with ice;	step one:Under nitrogen protection, 180 g of <strong>[27912-85-2]3-(benzyloxy)propionic acid</strong> was added to the reaction flask.1 L of dichloromethane, 95 g of oxalyl chloride was added dropwise under ice bath, and the reaction was carried out for 3 hours at room temperature.After completion of the reaction, the solvent was distilled under reduced pressure to give 180 g of Intermediate 1.Yield: 90%.
	With thionyl chloride; In N,N-dimethyl-formamide;	1-(2-Benzyloxyethyl)-3-(2-chloroethyl)-2-imidazolidinon, 22a To <strong>[27912-85-2]3-benzyloxypropionic acid</strong> (129.6 g) in ether (310 ml) and N,N-dimethylformamide (4 ml) was added thionyl chloride (155 ml). The solution was refluxed for 2 hours, and solvents and excess thionyl chloride were removed by evaporation in vacuo. Yield 132 g of 3-Benzyloxypropionic acid chloride as an oil.
	With thionyl chloride; In N-methyl-acetamide;	(b) Preparation of 3-benzyloxypropionyl chloride (VIII R1 =H, X=Cl) Thionyl chloride (60 ml) is added dropwise into a 500 ml four-necked flask fitted with a mechanical stirrer, a thermometer, a condenser and a dropping funnel, charged with <strong>[27912-85-2]3-benzyloxypropionic acid</strong> (100 g). Dimethylformamide (two drops) is then added while the temperature is kept at about 20 C. by means of a warm water bath. After stirring at room temperature for 2 hours the excess of thionyl chloride is removed by vacuum distillation and the residue is taken up twice with methylene chloride (two 100 ml portions). By evaporating the methylene chloride under reduced pressure 3-benzyloxypropionyl chloride (108.8 g) is obtained.

With oxalyl dichloride; N,N-dimethyl-formamide; In hexane; at 0℃; for 1h;

Cool a solution of <strong>[27912-85-2]3-benzyloxy-propionic acid</strong> (1.66 g, 9.19 mmol) in hexanes (40 mL) to 0C and add oxalyl chloride (3.50 g, 27.6 mmol) dropwise. After the addition is completed, add DMF (2 drops) and stir the resulting mixture for 1 hour. Remove the solvent under reduced pressure and dissolve the crude acid chloride in dry THF (20 mL). In a separate flask, dissolve 2-AMINO-4- (3-TRIFLUOROMETHYL-PYRIDIN-2-YL)-BENZAMIDE (2.35 g, 8. 37 mmol) in dry THF (40 mL) and pyridine (0.727 g, 9.19 mmol) and cool to 0C. Add the solution containing the crude acid chloride dropwise to the second solution. Allow the mixture to warm to room temperature and stir for 1 hour. Add a solution of 10% NaOH (aq) (20 mL) to the mixture and stir the solution for 1 hour. Concentrate the mixture (-20 mL), dilute with water (20 mL), and acidify with conc. HCI. Extract the resulting solution with ETOAC (3 x 50 mL). Wash the combined organic extracts with brine and dry over NA2S04. Remove the solvent under reduced pressure to yield the title compound as a white solid.

Reference： [1]Patent: CN110204522,2019,A .Location in patent: Paragraph 0024; 0025
[2]Recueil des Travaux Chimiques des Pays-Bas,1964,vol. 83,p. 81 - 93
[3]Synthetic Communications,1988,vol. 18,p. 1311 - 1322
[4]Journal of Organic Chemistry,1992,vol. 57,p. 3479 - 3482
[5]Journal of Organic Chemistry,1997,vol. 62,p. 7546 - 7547
[6]Journal of Medicinal Chemistry,1999,vol. 42,p. 706 - 721
[7]Journal of Organic Chemistry,2001,vol. 66,p. 697 - 706
[8]Journal of the American Chemical Society,2001,vol. 123,p. 9681 - 9682
[9]Patent: US5216001,1993,A
[10]Patent: US4576746,1986,A
[11]Chemistry - A European Journal,2008,vol. 14,p. 9240 - 9254
[12]Patent: WO2004/55003,2004,A1 .Location in patent: Page 57-58
[13]Journal of Organic Chemistry,2011,vol. 76,p. 1852 - 1873
[14]Angewandte Chemie - International Edition,2015,vol. 54,p. 15794 - 15798
Angew. Chem.,2015,vol. 127,p. 16020 - 16024,5
[15]Chemistry - A European Journal,2017,vol. 23,p. 13314 - 13318

2
[ 6328-48-9 ]
[ 4244-66-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 42 percent / HCl / 2.5 h / Heating 2: 85 percent / 1N NaOH(aq) / methanol / 0 deg C, 1 h -> room temperature, 3.5 h 3: SOCl₂ / 3 h / 40 - 50 °C

Reference： [1]Gutman, Arie L.; Meyer, Elazar; Boltanski, Aviv [Synthetic Communications, 1988, vol. 18, # 11, p. 1311 - 1322]

3
[ 4126-60-7 ]
[ 4244-66-0 ]

Reference： [1]Synthetic Communications,1988,vol. 18,p. 1311 - 1322

4
[ 4244-66-0 ]
[ 90719-32-7 ]
[ 1192145-95-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: (S)-4-Benzyl-2-oxazolidinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1.16667h; Inert atmosphere; Stage #2: 3-benzyloxypropionyl chloride In tetrahydrofuran at 20℃; for 1h;	157.1 [0388] Step 1: (S)-4-benzyl-3-(3-(benzyloxy)propanoyl) oxazolidin-2-one j0389] n-l3utyllithium, n-l3uEi (2.5 M in hexanes, 45.2 mE, 112.9 mmol) was added dropwise to a stirred solution of(45)-4-benzyl-1,3-oxazolidin-2-one (20.0 g, 112.9 mmol) in THF (300 mE) at -78° C. under N2 in 30 minutes. The reaction mixture was stirred at -78° C. for 45 mm, a solution of 3-benzyloxypropanoyl chloride (22.42 g, 112.9 mmol) in THF (100 mE) was added dropwise and the reaction waswarmed up slowly to room temperature and stirred for further 1 h. The reaction mixture was quenched with saturated NH4C1 solution (300 mE) and then extracted with EtOAc (300 mEx3). The combined organic layers were dried over anhydrous Na2504, filtered and concentrated. The residue was purified by column chromatography on silica (0-30% EtOAc in petroleum ether) to afford the title compound (29 g, yield 76%) as a light yellow solid. ‘H NMR (400 MHz, CD3OD) ö 7.37-7.20 (m, 1OH), 4.74-4.71 (m, 1H), 4.27-4.22 (m, 2H), 3.87-3.84 (m, 2H), 3.28-3.27 (m, 1H), 3.17-3.07 (m, 2H), 2.97-2.95 (m, 1H).
	With n-butyllithium at -78℃;

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2017/362228, 2017, A1 Location in patent: Paragraph 0388; 0389
[2]Diaz-Oltra, Santiago; Carda, Miguel; Murga, Juan; Falomir, Eva; Marco, J. Alberto [Chemistry - A European Journal, 2008, vol. 14, # 30, p. 9240 - 9254]

5
[ 4244-66-0 ]
[ 76186-04-4 ]
[ 1268600-38-9 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 1852 - 1873

6
[ 947-04-6 ]
[ 4244-66-0 ]
1-(3-(benzyloxy)propanoyl)azacyclotridecan-2-one [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 13947 - 13953
[2]Chemistry - A European Journal,2017,vol. 23,p. 13314 - 13318

7
[ 1213269-26-1 ]
[ 4244-66-0 ]
N-(3-(5-chloro-2-(2-methoxy-4-(4-methylpiperazin-1-yl)phenylamino)pyrimidin-4-yloxy)phenyl)-3-benzyloxypropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With triethylamine In acetone at 20℃;	General procedure XI for the synthesis of the 3-benzyloxypropanamide analogues (11, 21 and 32) General procedure: To a mixture of amine 4, 14 or 25 (400 mg, 0.91 mmol) and triethylamine (0.25 mL, 1.82 mmol) in acetone (8 mL) at 0 °C was added 3-benzyloxypropanoyl chloride (0.23 mL, 1.37 mmol) dropwise. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then filtered, the solvent was evaporated and water (6 mL) was added. The crude product was extracted three times with dichloromethane (3 x 6 mL) and washed with sodium bicarbonate solution (2 x 10 mL). The combined organic extract was dried over magnesium sulfate and concentrated. The crude product was purified by flash column chromatography dichloromethane-methanol (98:2) to obtain pure benzyloxy acetamide 11, 21 or 32 as white solids in yields ranging from 37 - 40%.

Reference： [1]Romu, Aireen A.; Lei, Zining; Zhou, Bin; Chen, Zhe-Sheng; Korlipara, Vijaya [Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 21, p. 4832 - 4837]

8
[ 1202-71-7 ]
[ 4244-66-0 ]
1-(3-(benzyloxy)propanoyl)azacyclododecan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: azacyclododecan-2-one With pyridine; dmap In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-benzyloxypropionyl chloride In dichloromethane at 50℃; for 16h; Inert atmosphere;

Reference： [1]Stephens, Thomas C.; Lawer, Aggie; French, Thomas; Unsworth, William P. [Chemistry - A European Journal, 2018, vol. 24, # 52, p. 13947 - 13953]

9
[ 10341-26-1 ]
[ 4244-66-0 ]
1,8-dioxa-4-azacycloundecane-5,9-dione [ No CAS ]

Reference： [1]Chemistry - A European Journal,2018,vol. 24,p. 13947 - 13953

10
[ 673-66-5 ]
[ 4244-66-0 ]
[ 26525-40-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 7-amino-heptanoic acid lactam With pyridine; dmap In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-benzyloxypropionyl chloride In dichloromethane at 50℃; for 16h; Inert atmosphere;

Reference： [1]Stephens, Thomas C.; Lawer, Aggie; French, Thomas; Unsworth, William P. [Chemistry - A European Journal, 2018, vol. 24, # 52, p. 13947 - 13953]

11
[ 673-66-5 ]
[ 4244-66-0 ]
1,8-dioxa-4-azacycloundecane-5,9-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 7-amino-heptanoic acid lactam With pyridine; dmap In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-benzyloxypropionyl chloride In dichloromethane at 50℃; for 28h; Inert atmosphere; Further stages;

Reference： [1]Stephens, Thomas C.; Lawer, Aggie; French, Thomas; Unsworth, William P. [Chemistry - A European Journal, 2018, vol. 24, # 52, p. 13947 - 13953]

12
[ 935-30-8 ]
[ 4244-66-0 ]
1-(3-(benzyloxy)propanoyl)azonan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: 2-azacyclononanone With pyridine; dmap In dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 3-benzyloxypropionyl chloride In dichloromethane at 50℃; for 16h; Inert atmosphere;

Reference： [1]Stephens, Thomas C.; Lawer, Aggie; French, Thomas; Unsworth, William P. [Chemistry - A European Journal, 2018, vol. 24, # 52, p. 13947 - 13953]

13
[ 774-05-0 ]
[ 4244-66-0 ]
ethyl 4,11-dioxooxacycloundecane-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: ethyl cycloheptanone-2-carboxylate With pyridine; magnesium chloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3-benzyloxypropionyl chloride In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #3: With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 18h;

Reference： [1]Lawer, Aggie; Epton, Ryan G.; Stephens, Thomas C.; Palate, Kleopas Y.; Lodi, Mahendar; Marotte, Emilie; Lamb, Katie J.; Sangha, Jade K.; Lynam, Jason M.; Unsworth, William P. [Chemistry - A European Journal, 2020, vol. 26, # 55, p. 12674 - 12683]

14
[ 4244-66-0 ]
[ 1196-38-9 ]
2-benzyl-3,4,7,8-tetrahydro-2,6-benzodiazecine-1,5-(2H,6H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 3,4-dihydroisoquinolin-1(2H)-one With pyridine; dmap In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3-benzyloxypropionyl chloride In dichloromethane at 50℃; Inert atmosphere; Stage #3: With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 16h;

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[ CAS No. 4244-66-0 ] {[proInfo.proName]}

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[ 4244-66-0 ] Synthesis Path-Downstream 1~14

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