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[ CAS No. 34376-54-0 ] 1,4-Diazepan-5-one

Cat. No.: A606508
Chemical Structure| 34376-54-0
Chemical Structure| 34376-54-0
Structure of 34376-54-0 * Storage: Keep in dark place,Inert atmosphere,2-8°C
Purity Size Price USA Stock *0-1 Day Global Stock *5-7 Days Quantity
95% 100mg $44.00 Inquiry Inquiry
95% 250mg $54.00 Inquiry Inquiry
95% 1g $110.00 Inquiry Inquiry
95% 5g $540.00 Inquiry Inquiry

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* Storage: Keep in dark place,Inert atmosphere,2-8°C

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Product Details of [ 34376-54-0 ]

CAS No. :34376-54-0 MDL No. :MFCD00766804
Formula : C5H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :QPPLBCQXWDBQFS-UHFFFAOYSA-N
M.W : 114.15 Pubchem ID :2737264
Synonyms :

Safety of [ 34376-54-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 34376-54-0 ]

* 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 [ 34376-54-0 ]

[ 34376-54-0 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 34376-54-0 ]
  • [ 24424-99-5 ]
  • [ 190900-21-1 ]
YieldReaction ConditionsOperation in experiment
89% In tetrahydrofuran; at 10 - 20℃; for 2h; Intermediate 5 :tert-butyl 5-oxo-l,4-diazepane-l-carboxylate; To a stirred solution of commercially available l,4-diazepan-5-one (3.3 g, 28.94 mmol) in THF cooled to 10°C, was added di-tert-butyl dicarbonate(9.5 g, 43.42 mmol) and the resultant reaction mixture was stirred at RT for 2 h. The reaction mixture was concentrated under reduced pressure and the resulting residue was washed with n-pentane (50 mL) to afford the title compound as a solid (5.5 g, 89percent).:H NMR (300 MHz, DMSO) delta = 7.62 (s, 1H), 3.45-3.40 (m, 4H), 3.12-3.08 (m, 2H), 2.43-2.39 (m, 2H).
795 mg With dmap; In dichloromethane; at 20℃; for 4h; 6.01.22.04 5-Oxo-1,4-diazepane-1-carboxylic acid tert-butyl ester 3.26 g di-tert-butyl dicarbonate 160.5 mg DMAP were added to 2,3,6,7-tetrahydro-(1H)-1,4-diazepin-5(4H)-one in 50 mL dichlormethane. The reaction was stirred 4 h at RT and washed with 10percent citric acid, saturated sodium hydrogencarbonate and saturated sodium chloride solution and evaporated. The residue was purified by column chromatographie on silica gel (cyclohexane/ethylacetate: 1/1) and crystallized from diethylether/petrolether:3/1 to yield 795 mg of the desired product. Rt: 0.98 min (method B), (M+H)+: 215
795 mg With dmap; In dichloromethane; at 20℃; for 4h; 6.01.22.04 5-Oxo- 1 , 4-diazepane- 1 -carboxylic acid tert-butyl ester 3.26 g di-tert-butyl dicarbonate 160.5 mg DMAP were added to 2, 3, 6, 7-tetrahydro-(lH)-l, 4- diazepin-5 (4H)-one in 50 mL dichlormethane. The reaction was stirred 4 h at RT and washed with 10percent) citric acid, saturated sodium hydro gencarbonate and saturated sodium chloride solution and evaporated. The residue was purified by column chromatographie on silica gel (cyclohexane/ ethylacetate: 1/1) and crystallized from diethylether/petrolether: 3/1 to yield 795 mg of the desired product. Rt: 0.98 min (method B), (M+H)+: 215
  • 2
  • [ 55186-89-5 ]
  • [ 34376-54-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; hydrogen;palladium(II) hydroxide; In methanol; at 45℃;Inert atmosphere; Step 3: Synthesis of l,4-diazepan-5-one [143]To a clean and dried two-necked RB flask taken compound [142] (600 mg, 2.93 mmol) was dissolved in eOH (15 ml). Concentrated HC1 (0.05 ml) and Pd(OH)2 ( 120 mg) were added sequentially under a nitrogen atmosphere. The reaction mixture was heated to 45 C under a hydrogen atmosphere and maintained at 45 C overnight. The reaction was monitored by mass analysis. Crude compound [143] obtained was used as such for the next step (350 mg, crude). ESIMS: 1 15 (M+ + 1 )
With hydrogenchloride; hydrogen; palladium(II) hydroxide; In methanol; at 45℃;Inert atmosphere; Step 3 To a clean and dried two-necked RB flask taken compound [111] (600 mg, 2.93 mmol) was dissolved in MeOH (15 ml). Concentrated HCI (0.05 ml) and Pd(OH)2 ( 120 mg) were added to the solution sequentially under a nitrogen atmosphere. The reaction mixture was heated to 45 C under a hydrogen atmosphere and maintained at 45 C overnight. The reaction was monitored by mass analysis. Crude compound [112] obtained was used as such for the next step (350 mg, crude). ESIMS: 1 15 (M+ + 1 )
  • 3
  • [ 34376-54-0 ]
  • [ 93107-30-3 ]
  • [ 141388-62-7 ]
YieldReaction ConditionsOperation in experiment
83% In acetonitrile; EXAMPLE 1 1-Cyclopropyl-6-fluoro-7-(2,3,4,5,6,7-hexahydro-1H-1,4-diazepin-5-one-1-yl)-4-oxoquinoline-3-carboxylic acid (Compound No. 1) 0,265 g of 1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid and 0.200 g of 2,3,4,5,6,7-hexahydro-1H-1,4-diazepin-5-one dissolved into 20 ml of acetonitrile and refluxed for 3 days. After cooling, the precipitate was collected by filtration, washed with chloroform, methanol, and ether in this order to obtain 0.300 g of colorless crystals of the target compound (yield: 83percent). IRnumaxKBr cm-1: 1720, 1660 1620 1 H-NHR delta ppm(NaOD+D2 O): 0.76-1.48(m, 4H), 2.50-3.80(m, 9H), 7.10(d, J=7.7 Hz, 1H), 7.56(d, J=14.1 Hz, 1H), 8.48(s, 1H) m.p.: 300° C. or above
  • 4
  • [ 190900-21-1 ]
  • [ 34376-54-0 ]
YieldReaction ConditionsOperation in experiment
With trifluoroacetic acid; In dichloromethane; at 20℃; for 3h; Intermediate I-50 (2.1 g, 10 mmol, 1.0 eq) was dissolved with dichloromethane (20 mL) and neat TFA (4 mL) was added. The reaction mixture was stirred at room temperature for 3 hours and excess solvent and TFA were removed by evaporation. The resulting crude intermediate I-51 (MS (ESI): m/z 115.1 (M+H+)), cyclobutanone (1.1 g, 15 mmol, 1.5 eq) and acetic acid (0.5 mL, 0.8 eq) were dissolved in dichloromethane (20 mL) and the reaction mixture was stirred at room temperature for 60 minutes. Solid NaBH(OAc)3 (4.2 g, 20 mmol, 2.0 eq) was added and the reaction mixture was stirred at room temperature for additional 3 hours. The reaction mixture was neutralized by adding an aqueous solution of K2CO3 and extracted with dichloromethane. The combined organic layers were dried over anhydrous MgSO4, the solids were removed by filtration and the filtrate was concentrated by evaporation to give the crude intermediate I-52 (1.6 g, 98percent) as white solid that was used in the following reaction without further purification. 1H-NMR (400 MHz, CDCl3) delta: 6.15 (s, 1H), 3.30 (q, J=4.8 Hz, 2H), 2.81 (q, J=4.4 Hz, 111), 2.61-2.63 (m, 2H), 2.45-2.50 (m, 4H), 2.03-2.10 (m, 2H), 1.79-1.88 (m, 2H), 1.62-1.74 (m, 2H). MS (ESI): m/z 169.1 (M+H+).
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Chemical Structure| 208245-76-5

A281374[ 208245-76-5 ]

1,4-Diazepan-5-one hydrochloride

Reason: Free-salt

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