475106-18-4|tert-Butyl 3-(aminomethyl)morpholine-4-carboxylate| Ambeed

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Quality Control of [ 475106-18-4 ] Purity: 98% SDS Specification

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Product Details of [ 475106-18-4 ]

CAS No. :	475106-18-4
Formula :	C₁₀H₂₀N₂O₃
M.W :	216.27
SMILES Code :	O=C(N1C(CN)COCC1)OC(C)(C)C
MDL No. :	MFCD06738665
InChI Key :	IRSSIQNSBCQILH-UHFFFAOYSA-N
Pubchem ID :	44182325

Safety of [ 475106-18-4 ]

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

Application In Synthesis of [ 475106-18-4 ]

* 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 [ 475106-18-4 ]

[ 475106-18-4 ] Synthesis Path-Downstream 1~42

1
[ 475106-18-4 ]
[ 139631-62-2 ]
3-(cyclopropanesulphonylamino-methyl)-morpholine-4-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃; for 1.5h;	Example 19; The following representative example illustrates the synthesis of an amine educt in the morpholine series. Procedure for making an intermediate according to Scheme H. 3-(Cyclopropanesulphonylamino-methyl)-morpholine-4-carboxylic acid tert-butyl esterTo a solution of 21 mg (0.10 mmol) 3-Aminomethyl-morpholine-4-carboxylic acid tert-butyl ester (prepared according to Example 18, steps 1, 2 and 3) and 15 μL (0.12 mmol) of triethylamine in 3 mL of dichloromethane at 0 C. is added 15 mg (0.11 mmol) of cyclopropanesulphonyl chloride. After stirring for 1.5 h at room temperature dichloromethane is added. The organic solution is washed successively with a 5% aqueous citric acid solution, with a saturated aqueous sodium bicarbonate solution and with brine. After drying over sodium sulphate and evaporating the solvent under reduced pressure, the title compound, was obtained which was used crude in the next step without further purification.LC/MS (II) rt 2.26, m/z 384 [M+H+CH3CN]+.

References: [1]Patent: US2008/176838,2008,A1 .Location in patent: Page/Page column 24.

2
[ 475106-18-4 ]
[ 501-53-1 ]
[ 1154870-84-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 0 - 20℃; for 2.0h;	Step 2: tert-Butyl 3-({r(benzyloxy)carbonyl1amino}methyl)morpholine-4-carboxylate (RR2) A solution (0.15 M) of Cbz-Cl (1.7 eq) in DCM was added dropwise to an ice cold-solution (0.15 M) of RRl (1 eq) and Et3N (1.8 eq) in DCM and the mixture was stirred at RT for 2 h. The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography on silica gel, eluting with 10-30% EtO Ac/Petroleum ether to afford the title compound RR2. 1H-NMR (300 MHz, DMSO-d6, 300K) δ: 7.33 (5H, br. s), 4.99 (2H, s), 4.10- 3.89 (IH, m), 3.78-3.55 (3H, m), 3.45-3.00 (6H, m), 1.37 (9H, s). MS (ES) Ci8H26N2O5 required: 350, found: 373 (M+Na)+.
464 mg	With triethylamine; In tetrahydrofuran; at 20℃; for 2.0h;	To a solution of <strong>[475106-18-4]tert-butyl 3-(aminomethyl)morpholine-4-carboxylate</strong> (287 mg) in THF (10 mL) were added benzyl chloroformate (226 mg) and TEA (134 mg), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give tert-butyl 3-((((benzyloxy)carbonyl)amino)methyl)morpholine-4-carboxylate (464 mg). 1H NMR (300 MHz, CDCl3) δ 1. 43 (9H, s), 2.94-3.37 (2H, m), 3.44 (1H, td, J = 11.8, 2.8 Hz), 3.57 (1H, dd, J = 11.7, 3.4 Hz), 3.65-3.93 (4H, m), 4.02-4.19 (1H, m), 5.00 (1H, brs), 5.09 (2H, s), 7.28-7.43 (5H, m).

References: [1]Patent: WO2009/63244,2009,A1 .Location in patent: Page/Page column 109.
[2]Patent: EP3187497,2017,A1 .Location in patent: Paragraph 0322.

3
[ 518047-40-0 ]
[ 475106-18-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;platinum(IV) oxide; In methanol; under 2585.81 Torr;	Step 1: ferf-Butyl 3-(aminomethyl)morpholine-4-carboxylate (RRl) <n="110"/>- -To a solution (0.3 M) of tert-butyl 3-cyano-4-morpholinecarboxylate (prepared as described in the J Med. Chem. 2007, 50, 4953-4975) in MeOH was added PtO2 (0.1 eq) and the mixture was stirred O/N under an H2 atmosphere at 50psi. The reaction mixture was filtered and concentrated under reduced pressure to afford the title compound RRl. MS (ES) C10H20N2O3 required: 216, found: 217 (M+H)+.

References: [1]Patent: WO2009/63244,2009,A1 .Location in patent: Page/Page column 108-109.

4
[ 475106-18-4 ]
3‐[8‐(1‐methyl‐1H‐indol‐6‐yl)quinoxalin‐6‐yl]amino}pyridine‐4‐carboxylic acid [ No CAS ]
tert‐butyl 3‐[(3‐[8‐(1‐methyl‐1H‐indol‐6‐yl)quinoxalin‐6‐yl]amino}pyridin‐4‐yl)formamido]methyl}morpholine‐4‐carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; at 20℃; for 48.0h;	3-[8-(1 -Methyl-1 H-indol-6-yl)quinoxalin-6-yl]amino}pyridine-4-carboxylic acid (70 mg; 0.18 mmol; 1 eq.), EDC-HCI (41 mg; 0.21 mmol; 1.20 eq.) and HOBt hydrate (33 mg; 0.21 mmol; 1.20 eq.) are dissolved in dioxane (7 ml_) at room temperature. Triethylamine (0.11 ml0.88 mmol; 5 eq.) is added followed by methylamine hydrochloride (18 mg; 0.26 mmol; 1.50 eq.), after 30 minutes of stirring. After 24 hours at room temperature, UPLC-MS analysis shows 75% conversion and extra portions of Λ -(3- dimethylaminopropyl)-/S '-ethylcarbodiimide hydrochloride (21 mg; 0.11 mmol; 0.60 eq.) and HOBt hydrate (16.5 mg; 0.11 mmol; 0.60 eq.) are added and the reaction is continued for another 24 h. Dioxane is then evaporated and the residue is vigorously stirred in a mixture of water and EtOAc. The medium is neutralized with 1 M HCI and the phases are separated. The aqueous phase is extracted twice with EtOAc. The combined organic layers are washed with water and brine, dried over anhydrous Na2S04, filtered, concentrated and purified by FCC (0-100% EtOAc gradient in hexane and continued with 0-10% MeOH gradient in EtOAc) to afford A/-methyl-3-[8-(1- methyl-1 /- -indol-6-yl)quinoxalin-6-yl]amino}pyridine-4-carboxamide (62 mg; 0.15 mmol; yield: 83%; yellow powder; HPLC purity: 97%).
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In 1,4-dioxane; at 20℃; for 24.0h;Inert atmosphere;	General procedure: 3-[8-(1-Methyl-1H-indol-6-yl)quinoxalin-6-yl]amino}pyridine-4-carboxylic acid6[11](70 mg; 0.18 mmol; 1 eq.),EDC•HCl(62 mg; 0.32 mmol; 1.8 eq.) andHOBt hydrate(50 mg; 0.32 mmol; 1.8 eq.) were dissolved in dioxane (7 mL) at room temperature. Triethylamine (0.11 mL; 0.88 mmol; 5 eq.) was added followed by methylamine hydrochloride (18 mg; 0.26 mmol; 1.5 eq.), after 30 minutes. After 48 hours of stirring at room temperature under argon, dioxane was evaporatedin vacuoand the residue was vigorously stirred in a 1:1 (v/v, 50 mL) mixture of water and EtOAc. The medium was neutralized with 1M HCl and the phases were separated. The aqueous phase was extracted twice with EtOAc, and the combined organic layers were washed with water and brine, dried over anhydrous Na2SO4, filtered, and concentratedin vacuo. The resulting residue waspurified by automated flash chromatography (0-100% EtOAc gradient in hexane and continued with 0-10% MeOH gradient in EtOAc)to affordN-methyl-3-[8-(1-methyl-1H-indol-6-yl)quinoxalin-6-yl]amino}pyridine-4-carboxamide11as a yellow powder (62 mg; 0.15 mmol; yield: 83%; LCMS purity: 97%, method B).

References: [1]Patent: WO2016/180537,2016,A1 .Location in patent: Page/Page column 226; 227.
[2]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 646 - 653.

5
[ 475106-18-4 ]
[ 340736-76-7 ]
tert-butyl 3-(((4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzoyl)amino)methyl)morpholine-4-carboxylate [ No CAS ]