719999-54-9|(R)-tert-Butyl (pyrrolidin-2-ylmethyl)carbamate| Ambeed

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Quality Control of [ 719999-54-9 ] Purity: 95% SDS Specification

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Product Details of [ 719999-54-9 ]

CAS No. :	719999-54-9
Formula :	C₁₀H₂₀N₂O₂
M.W :	200.28
SMILES Code :	O=C(OC(C)(C)C)NC[C@@H]1NCCC1
MDL No. :	MFCD03839886
InChI Key :	DPJPFGHHTJLWQQ-MRVPVSSYSA-N
Pubchem ID :	22883086

Safety of [ 719999-54-9 ]

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

Application In Synthesis of [ 719999-54-9 ]

* 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 [ 719999-54-9 ]

[ 719999-54-9 ] Synthesis Path-Downstream 1~32

1
[ 719999-54-9 ]
[ 119736-16-2 ]
[ 1309561-94-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; for 16h;	3) (R)-2-N-BOC-aminomethj'l pyrrolidine (391mg, l,95mmol) was added to the solution of compound 101 (400mg, J .62nvmol), EPO <DP n="116"/>1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloridc (373mg, l,95mmol), and 1-hydroxybenzotriazole (219mg, 1.62mmol) in THF (6ml). After sttiring for 16h NaHCOa aqueous solution was added to the mixture, The mixture was extracted with EtOAc, which was washed with NH/jCl aqueous solution and brine, The organic phase was dried over MgSO-i, After a filtration the solvent was removed under reduced prosRurG to obtain compound 102 (694mg, 100%) as a white solid. 1H-NMR (CDCl3)delta; 1.4beta(9H, s), 1.56-2.14(4H, m), 3.29(4H, m), 4.18(1H, m), 5.24( LH, s), 6.27(1H, s), 6.46(1H, d, J=5.7Hz), 7,35(5H, m), 7.69(1H, d, J=5.7HSU) .

References: [1]Patent: WO2006/116764,2006,A1 .Location in patent: Page/Page column 113-114.

2
[ 719999-54-9 ]
[ 19524-06-2 ]
[ 1044272-13-0 ]

Yield	Reaction Conditions	Operation in experiment
28%		(R)-Pyrrolidin-2-ylmethyl-carbamic acid tert-butyl ester (80mg; 0.99 mmol), 4-bromopyridine hydrochloride (77mg; 0.99 mmol), NaOH 10% (0.2 ml) and 1,4-dioxane (0.2 ml) were mixed together. The reaction mixture was irradiatedin a microwave reactor (CEM; 15 W, ramp 5 min.; hold 25 min.; 130 C; 150 psi), then stirred at 70 C overnight.The reaction mixture was concentrated under reduced pressure and the crude was treated with 0.2 ml of 1,4-dioxane,1 ml of water and 0.5 ml of HCI 37%. The reaction mixture was maintained at room temperature for 3h, then treatedwith 2 ml of NaOH 10% and diluted with 10 ml of dichloromethane. The organic phase was separated, dried on MgSO4and concentrated under reduced pressure. 50 mg (0.282 mmol; 28%) of the desired product were obtained.

References: [1]Patent: EP1953163,2008,A1 .Location in patent: Page/Page column 18-19.

3
[ 719999-54-9 ]
[ 954408-79-8 ]
tert-butyl ((R)-1-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5λ4-thieno[3,2-d]pyrimidin-4-yl}-pyrrolidin-2-ylmethyl)-carbamidate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 120℃; for 0.3h;Microwave irradiation;	3.16.1 tert.Butyl((R)-1-{2-[4-(4-chloro-phenyl)-piperazin-1-yl]-5-oxo-6,7-dihydro-5H-5lambda4-thieno[3,2-d]pyrimidin-4-yl}-pyrrolidin-2-ylmethyl)-carbamidate, Example 219 Scheme 3, Step D 200 mg of 4-chloro-2-[4-(4-chloro-phenyl)-piperazin-1-yl]-6,7-dihydro-thieno[3,2-d]pyrimidine 5-oxide (cf Example 124), 314 mg <strong>[719999-54-9](R)-2-N-BOC-aminomethylpyrrolidine</strong> and 179.6 mul diisopropylethylamine are placed in 4 ml DMF and heated to 120 C. in the microwave for 0.3 hours. Then the reaction mixture is acidified with trifluoroacetic acid and mixed with water. The product is separated by semipreparative HPLC (method A). 68 mg product (Example 219) are obtained as a powder. Analytical HPLC-MS (method B): RT=2.0 min.

References: [1]Patent: US2008/96882,2008,A1 .Location in patent: Page/Page column 98; 44.

4
[ 719999-54-9 ]
[ 288083-40-9 ]
[ 1186121-16-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4034 - 4041.

5
[ 719999-54-9 ]
[ 1037754-93-0 ]
[ 1204310-49-5 ]

Yield	Reaction Conditions	Operation in experiment
		HOBt-H2O (91.0 mg, 672 mumol) and EDCI (129 mg, 672 mumol) were added to a stirred solution of 4-{3-[l-(3-isopropyl-[l,2,4]oxadiazol-5-yl)piperidin-4-yl]propoxy}-2-methylbenzoic acid (Preparation 9, 200 mg, 517 mumol) in THF (12 mL). After 0.5 h, (R)-I -pyrrolidin-2- ylmethylcarbamic acid terZ-butyl ester (207 mg, 1.033 mmol) was added and the resulting mixture was stirred at ambient temperature for 16 h. The THF was removed in vacuo and the residue was partitioned between EtOAc and 2M NaOH. The organic phase was separated and washed with 2M NaOH, IM HCl and brine, before being dried (MgSO4). Filtration, solvent evaporation, and purification by column chromatography ((EtOAc-IH, 1:1 to 1:0) afforded [(R)- 1 -(4- { 3- [ 1 -(3-isopropyl-[ 1 ,2,4] oxadiazol-5 -yl)piperidin-4-yl]propoxy } -2-methylbenzoyl)- pyrrolidin-2-ylmethyl]carbamic acid tert-butyl ester: RT = 4.10 min; mlz (ES+) = 570.39 [M + H]+ (Method A). To a stirred solution of this compound in dioxane (5 mL) was added 4M HCl in dioxane (1.08 mL, 4.29 mmol) and the resulting solution was stirred at ambient temperature for 5 h. The solvent was removed in vacuo and the remainder was dissolved in H2O and washed with EtOAc. The aqueous was basified to pH 12 with 2M NaOH and extracted with EtOAc (3x). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to afford the title compound: RT = 2.97 min; mlz (ES+) = 470.31 [M + H]+ (Method A).

References: [1]Patent: WO2010/4347,2010,A1 .Location in patent: Page/Page column 37-38.

6
[ 719999-54-9 ]
[ 1314605-38-3 ]