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[ CAS No. 122181-85-5 ]

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2D
Chemical Structure| 122181-85-5
Chemical Structure| 122181-85-5
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SDS

Product Details of [ 122181-85-5 ]

CAS No. :122181-85-5MDL No. :MFCD11226170
Formula :C6H8N2O2Boiling Point :272.3°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :140.14Pubchem ID :14104599
Synonyms :

Computed Properties of [ 122181-85-5 ]

TPSA : 57.2 H-Bond Acceptor Count : 3
XLogP3 : 1.2 H-Bond Donor Count : 1
SP3 : 0.17 Rotatable Bond Count : 2

Safety of [ 122181-85-5 ]

Signal Word:WarningClassN/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 122181-85-5 ]

  • Upstream synthesis route of [ 122181-85-5 ]
  • Downstream synthetic route of [ 122181-85-5 ]

[ 122181-85-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1193-62-0 ]
  • [ 122181-85-5 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; Inert atmosphere
Stage #2: With O-(2,4-dinitrophenyl)hydroxylamine In N,N-dimethyl-formamide; mineral oil at 0℃;
(Step 1) methy 1-amino-1H-pyrrolo-2-carboxylate; To a mixture of NaH (60percent, 4.1 g, 102.2 mmol) suspended in dimethylformamide (120 mL) at 0° C. under nitrogen atmosphere, methyl pyrrolo-1-H-2-carboxylate (8.0 g, 63.9 mmol) was slowly added over minutes. After stirring for 1 hour, a solution of 2,4-dinitrophenolamine (19.1 g, 95.9 mmol) in dimethylformamide (30 mL) was added dropwise for 30 minutes. The resulting reaction mixture was stirred at 0° C. for 2.5 hours. The reaction was completed by slowly adding saturated sodium thiosulfate aqueous solution. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with 10percent lithium chloride aqueous solution, dried with sodium sulfate, and then filtered. The filtrate was concentrated. The resulting brown residue was purified by silica gel chromatography (10percent ethyl acetate in hexane) to give the target compound as an oil (7.5 g, 53.5 mmol, 84percent yield).1H NMR (400 MHz, CDCl3): 6.96 (t, J=2.4 Hz, 1H), 6.83 (dd, J=4.4 Hz, 2.0 Hz, 1H), 6.02 (dd, J=4.4 Hz, 2.8 Hz, 1H) 5.54 (br s, 2H), 3.83 (s, 3H).
81.1%
Stage #1: With sodium hydride In hexanes; N,N-dimethyl-formamide at -5℃; Inert atmosphere
Stage #2: With diphenyl aminooxyphosphonate In hexanes; N,N-dimethyl-formamide at 20℃; for 4.00 h;
Stage #3: With sodium thiosulfate In hexanes; water; N,N-dimethyl-formamide at 80℃; for 1.00 h;
a) Methyl 1 -amino-1 W-pyrrole-2-carboxylateSodium hydride (4.40 g, 0.1 1 mol, 60percent in hexanes) was suspended in DMF (550 ml) under nitrogen atmosphere. Once cooled at - 5°C, methyl 1 H-pyrrole-2-carboxylate (1 1 .0 g, 0.09 mol) dissolved in DMF (182 ml) was dropwise added and vigorously stirred for 30. 277ml more of DMF was added and then O- (diphenylphosphoryl)hydroxylamine (32.8g, 0.14 mol) was introduced into the reaction mixture. The reaction mixture was stirred at room temperature for 4h. Once the reaction is over, 11 of saturated sodium thiosulfate solution (x5H20) was added and the mixture was warmed to 80°C for 1 h. Once at room temperature, 11 of ethyl ether was added and the phases separated. The aqueous phase was twice extracted with ethyl ether. The organic phase was washed with water and brine, dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. 10.41 g (81 .1 percent yield) of the final compound were obtained.LRMS (m/z): 141 (M+1 )+
Reference: [1] Patent: US2011/183983, 2011, A1. Location in patent: Page/Page column 32
[2] Patent: WO2012/146666, 2012, A1. Location in patent: Page/Page column 172
[3] Patent: US2010/47367, 2010, A1. Location in patent: Page/Page column 22
[4] Patent: WO2010/71885, 2010, A1. Location in patent: Page/Page column 335
[5] Patent: WO2016/144848, 2016, A1. Location in patent: Page/Page column 33
[6] Patent: CN105524068, 2016, A. Location in patent: Paragraph 0171; 0173
  • 2
  • [ 122181-83-3 ]
  • [ 122181-85-5 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 9, p. 2894 - 2906
[2] Tetrahedron Letters, 1988, vol. 29, # 38, p. 4823 - 4826
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