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[ CAS No. 23356-96-9 ]

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CAS No. :23356-96-9 MDL No. :MFCD00005255
Formula : C5H11NO Boiling Point : 211°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :101.15 g/mol Pubchem ID :640091
Synonyms :

Safety of [ 23356-96-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23356-96-9 ]

  • Upstream synthesis route of [ 23356-96-9 ]
  • Downstream synthetic route of [ 23356-96-9 ]

[ 23356-96-9 ] Synthesis Path-Upstream   1~23

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Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 8, p. 2737 - 2743
[2] Journal of the Chemical Society, 1958, p. 4458,4462
[3] Journal of Organometallic Chemistry, 1983, vol. 246, # 1, p. 53 - 56
[4] Tetrahedron Letters, 1995, vol. 36, # 43, p. 7885 - 7888
[5] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 19, p. 2891 - 2896
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Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 35, p. 6171 - 6173
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  • [ 17342-08-4 ]
Reference: [1] Patent: US2004/225133, 2004, A1, . Location in patent: Page 6-7
[2] Patent: US2004/225133, 2004, A1, . Location in patent: Page 7
[3] Patent: US2004/225133, 2004, A1, . Location in patent: Page 7
[4] Patent: US2004/225133, 2004, A1, . Location in patent: Page 7
[5] Patent: US2004/225133, 2004, A1, . Location in patent: Page 7
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Reference: [1] Patent: US2004/225133, 2004, A1, . Location in patent: Page 6
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Reference: [1] Patent: US5137905, 1992, A,
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  • [ 51207-66-0 ]
Reference: [1] Tetrahedron, 1987, vol. 43, # 14, p. 3289 - 3294
[2] Tetrahedron Asymmetry, 1990, vol. 1, # 12, p. 877 - 880
[3] Chemistry - A European Journal, 2017, vol. 23, # 68, p. 17195 - 17198
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  • [ 22795-99-9 ]
Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 5, p. 1612 - 1624
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  • [ 53912-80-4 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 8, p. 2737 - 2743
[2] Dyes and Pigments, 2011, vol. 90, # 2, p. 100 - 105
[3] Synlett, 2005, # 8, p. 1235 - 1238
[4] Tetrahedron Letters, 2005, vol. 46, # 20, p. 3579 - 3582
[5] Journal of Organometallic Chemistry, 2007, vol. 692, # 24, p. 5459 - 5473
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 12, p. 2887 - 2893
[7] RSC Advances, 2015, vol. 5, # 5, p. 3461 - 3464
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Reference: [1] Synthesis, 2010, # 10, p. 1673 - 1677
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Reference: [1] Synthesis, 2002, # 3, p. 375 - 380
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Reference: [1] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 7, p. 2199 - 2206
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  • [ 142253-50-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2000, vol. 43, # 3, p. 342 - 345
[2] Bulletin de la Societe Chimique de France, 1997, vol. 134, # 7, p. 713 - 718
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YieldReaction ConditionsOperation in experiment
76% With triethylamine In dichloromethane at 20℃; To a solution of (S)-pyrrolidin-2-yl-methanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0° C. was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature over night and poured into NH4Cl (20 mL). The aqueous layer was extracted with DCM (2×50 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (1.11 g, 76percent) as a yellow oil. MS: 216.2 (M+H+)
76% With triethylamine In dichloromethane at 0 - 20℃; Intermediate A-36-{5-[(S)-2-(tei"i-Butyl-dimethyl-silanyloxymethyl)-pyrrolidin-l-yl]-pyridin-3-yl}-l- methyl-3,4-dihydro-lH-quinolin-2-one [A] (S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidineTo a solution of (S)-pyrrolidin-2-yl-methanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0 °C was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature over night and poured into NH4C1 (20 mL). The aqueous layer was extracted with DCM (2 x 50 mL). Combined organics were washed with brine, dried over Na2S04, filtered and evaporated to dryness to give the title compound (1.11 g, 76percent) as a yellow oil. MS: 216.2 (M+H+).
76% With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere To a solution of (S)-pyrrolidin-2-ylmethanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0 °C was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL). The reaction mixture was then stirred at room temperature over night and poured into NH4C1 (20 mL). The aqueous layer was extracted with DCM (2 x 50 mL). Combined organics were washed with brine, dried over Na2S04, filtered and evaporated to dryness to give the title compound (1.1 lg, 76percent) as a yellow oil. MS: 216.2 (M+H+).
76% With triethylamine In dichloromethane at 0 - 20℃; [A]
(S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-pyrrolidine
To a solution of (S)-pyrrolidin-2-ylmethanol (0.69 g, 6.82 mmol) in DCM (3 mL) cooled to 0° C. was added TEA (1.38 g, 13.6 mmol) followed by TBDMS-Cl (1.03 g, 6.82 mmol) in DCM (3 mL).
The reaction mixture was then stirred at room temperature overnight and poured into NH4Cl (20 mL).
The aqueous layer was extracted with DCM (2*50 mL).
Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (1.11 g, 76percent) as a yellow oil. MS: 216.2 (M+H+).

Reference: [1] Synlett, 2007, # 15, p. 2415 - 2419
[2] Patent: US2013/72679, 2013, A1, . Location in patent: Paragraph 0553; 0554
[3] Patent: WO2013/37779, 2013, A1, . Location in patent: Page/Page column 76; 77
[4] Patent: WO2013/79452, 2013, A1, . Location in patent: Page/Page column 237
[5] Patent: US2013/143863, 2013, A1, . Location in patent: Paragraph 1082; 1083; 1084
[6] Chemical and Pharmaceutical Bulletin, 2007, vol. 55, # 2, p. 328 - 333
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YieldReaction ConditionsOperation in experiment
74% for 1 h; (1) Fmoc-L-Prolinol (Compound 2)L-prolinol (Compound 1) (0.61 g, 6.0 mmol) was dissolved in 70 ml of pure water, thus preparing an L-prolinol aqueous solution. N-(9-Fluorenylmethoxycarbonyloxy)succinimide (Fmoc-OSu) (2.0 g, 6.0 mmol) was dissolved in 10 ml ofTHF. This THF solution was added to the L-prolinol aqueous solution, and this was stirred for 1 hour so as to react the L-prolinol and the Fmoc-OSu. The reaction solution was separated into a liquid fraction and a precipitate fraction. These fractions respectively were subjected to extraction with ethyl acetate, and organic layers respectively were collected therefrom. The thus-obtained organic layers were mixed together, and anhydrous sodium sulfate was added thereto to absorb moisture (hereinafter, this process is referred to as a “drying” process). The organic layers were filtered, and the filtrate obtained was vacuum concentrated. The residual substance obtained was purified by silica gel column chromatography (the eluent: hexane:ethyl acetate=1 :1). Thus, Compound 2 was obtained (1.4 g, yield: 74percent). The result of NMR analysis with respect to this compound is shown below.‘H-NMR (CDC13): ö7.77 (2H, d, J=7.7 Hz, Ar——H), 7.60 (2H, d, J=7.3 Hz,Ar—H), 7.40(2H,t, J=7.5 Hz,Ar—H), 7.31 (2H, t, J=7.6 Hz, Ar—-H), 4.40-4.50 (2H, m, COOCH2), 4.22(1H, t, J=6.5 Hz,Ar-CH), 3.20-3.80 (5H, m, H-5, H-6), 1.75(3H, m, H-3, H-4), 1.40 (1H, m, H-3).
Reference: [1] Patent: US9200278, 2015, B2, . Location in patent: Page/Page column 39; 40; 41; 42
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Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 12, p. 4023 - 4034
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Reference: [1] Nucleosides, Nucleotides and Nucleic Acids, 2001, vol. 20, # 4-7, p. 1377 - 1379
[2] Tetrahedron, 2010, vol. 66, # 51, p. 9703 - 9707
[3] Tetrahedron Letters, 2011, vol. 52, # 5, p. 615 - 618
[4] Journal of the Korean Chemical Society, 2013, vol. 57, # 5, p. 591 - 598
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2014, vol. 57, # 4, p. 209 - 214
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YieldReaction ConditionsOperation in experiment
74%
Stage #1: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.25 h;
Stage #2: at 20℃; for 4 h;
Compound 26 (0.78 g, 1.7 mmol) was dissolved in 1.7 ml anhydrous DMF and anhydrous DIPEA (0.87 g, 6.74 mmol) was added at 0 ° C. After stirring at 0 ° C for 15 min, compound 9 (340 mg, 3.37 mmol). After reaction at 20 ° C for 4 hours, column chromatography purified Compound 1, avanafil (600 mg, 74percent yield).
0.7 g With triethylamine In ethyl acetate at 20 - 30℃; 0.9g of compound X obtained in step (4) was dissolved in 15ml of ethyl acetate, 196mg of L-prolinol and 0.54ml of triethylamine were directly added into the organic phase, and stirred for 1-16h at 20-30 ° C. 40ml Water and 45ml ethyl acetate. The organic phase was separated, the organic phase was washed three times with 5percent sodium carbonate solution (30ml × 3), then with saturated brine and washed three times with water (30ml × 3), dried over anhydrous sodium sulfate The organic phase was filtered and concentrated under reduced pressure to give 0.7 g of a white solid.
Reference: [1] Patent: CN104710411, 2017, B, . Location in patent: Paragraph 0025; 0104; 0105; 0106; 0107; 0108
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5460 - 5465
[3] Patent: CN104059025, 2017, B, . Location in patent: Paragraph 0097; 0098; 0099
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YieldReaction ConditionsOperation in experiment
97% With 1H-imidazole In toluene at 20℃; for 18 h; The above prepared 39g ivah that non-intermediate B4-[ (3-chloro-4-benzyl) amino]-2-methylthio-N-(2-pyrimidinyl methyl)-5-pyrimidine carboxamide dissolved in 200 ml acetonitrile is formed in the reaction solution, then adding 13.8gL- dried meat ammonia alcohol and 9.5g pyridine, the reaction stirring under room temperature for 19 hours, evaporate most of the acetonitrile, then adding ethyl acetate, then with water, saturated sodium bicarbonate, the saturated salt water, the organic phase is dried with anhydrous sodium sulfate, filtered, by reduced pressure evaporation to dryness the crude product to 46g, crude product with ethyl acetate/n-heptane is recrystallized, get 37g non- ivah that final product. The purity of 97percent, the yield is 79.5percent
1.1 g at 20 - 30℃; for 1 h; 215 mg of L-prolinol and 1 ml of triethylamine were directly added to the organic phase of the compound VIII obtained in the step (4), and the mixture was stirred at 20 to 30 ° C for 1 hour. The reaction mixture was added with 50 ml of water and the organic phase was separated. The organic phase was washed three times (30 ml x 3) with 5percent sodium carbonate solution and three times with saturated brine (30 ml x 3). The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 1.1 g of a white solid by crystallization. Yield in three steps was 77.5percent.
Reference: [1] Patent: CN103483323, 2016, B, . Location in patent: Paragraph 0075; 0079
[2] Patent: CN104059025, 2017, B, . Location in patent: Paragraph 0049; 0050; 0051; 0065; 0066; 0067; 0081-0083
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YieldReaction ConditionsOperation in experiment
97.2% With triethylamine In tetrahydrofuran at 20℃; for 20 h; The above prepared 41.5g ivah that non-intermediate B2-chloro-4-[ (3-chloro-4-benzyl) amino)-N-(2-pyrimidinyl methyl)-5-pyrimidine carboxamide dissolved in 200 ml of tetrahydrofuran is formed in the reaction solution, then adding 10gL- dried meat ammonia alcohol and 10g triethylamine, the reaction stirred at room temperature 20 hours, evaporate most of the tetrahydrofuran, then added with ethyl acetate, then with water, saturated sodium bicarbonate, the saturated salt water, the organic phase is dried with anhydrous sodium sulfate, filtered, pressure-reducing evaporation did 45.0g crude product, crude product with ethyl acetate/n-heptane is recrystallized, produce a final product 34.8g ivah that non-. The purity is 97.2percent, the yield is 70.3percent.
Reference: [1] Patent: CN103483323, 2016, B, . Location in patent: Paragraph 0071
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YieldReaction ConditionsOperation in experiment
81.3%
Stage #1: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20 - 60℃; for 24 h; Inert atmosphere
Stage #2: With sodium hydride In tetrahydrofuran at 65℃; for 5 h;
With the protection of nitrogen, 2.0 g of 6-(3-chloro-4-methoxy-benzylamino)-1,2-dihydro-pyrimidin-2-one-5-(N-2-methyl-pyrimidinyl) formamide (VII) (5 mmol), 3.31 g of benzotriazol-1-yloxytris (dimethylamino)-phosphonium hexafluorophosphate (BOP) (7.5 mmol) and 25 mL of acetonitrile in a three-necked flask. 1.15 g of 1,8-diazabicyclo[5.4.0]undec-7-ene(DBU) (7.5 mmol) was added dropwise while stirring, and reacted 12 hours at room temperature; then heated to 60° C. for reaction 12 hours. The solvent was removed by distillation under reduced pressure, then added to 50 mL ethyl acetate to dissolve, and washed with 10 mL of 2M sodium hydroxide. The organic phase was separated, dried and concentrated under reduced pressure, then the residue was dissolved in 50 mL of tetrahydrofuran, added with S-hydroxymethyl pyrrolidine (II) (0.61 g, 6 mmol) and sodium hydride (0.16 g, 6 mmol), heated to 65° C. and stirred for reaction for 5 hours, then the reaction ended with the TLC monitoring. After quenching with saturated brine the reaction, the organic phase was separated, dried and distilled under reduced pressure to recover the solvent. The resulting solid was recrystallized with ethanol to get 1.96 of white solid avanafil (I), with the yield of 81.3percent.
Reference: [1] Patent: US2016/75693, 2016, A1, . Location in patent: Paragraph 0037
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  • [ 41965-95-1 ]
  • [ 2972-52-3 ]
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YieldReaction ConditionsOperation in experiment
64%
Stage #1: With triethylamine In dichloromethane for 1 h; Cooling with ice
Stage #2: With triethylamine In dichloromethane for 2 h;
Stage #3: at 20℃;
A solution of 2,4-dichloro-5-pyrimidinecarbonyl chloride (0.6 g, 2.8 mmol) in dichloromethane (8 ml) was added to a 50 ml three-necked flask and cooled in an ice bath. The 2-aminomethylpyrimidine acetate (0.48 g, 2.8 mmol) and triethylamine (2.8 mmol) were first dissolved in dichloromethane,And then dropwise dropwise into the reaction solution. Plus finished, the reaction 1 hour,A mixture of 3-chloro-4-methoxybenzylamine hydrochloride (0.59 g, 2.8 mmol) and triethylamine (0.29 g, 2.8 mmol) was added dropwise to the above reaction solution, 2 hours,To the reaction solution was added L-proline alcohol (0.43 g, 4.3 mmol), and the reaction was carried out overnight at room temperature.The reaction solution was poured into ice water, quenched and extracted twice with methylene chloride. The organic phase was combined and washed twice with water,Dried over anhydrous sodium sulfate and concentrated to give the crude product which was purified by column chromatography to give 0.9 g of white solid, and the yield was 64percent.
Reference: [1] Patent: CN104650045, 2017, B, . Location in patent: Paragraph 0112; 0113
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YieldReaction ConditionsOperation in experiment
32%
Stage #1: for 2 h;
Stage #2: at 20℃; for 4 h;
A solution of 3-chloro-4-methoxybenzylamine hydrochloride (0.59 g, 2.8 mmol)And triethylamine (0.29 g, 2.8 mmol) were added dropwise to the above-mentioned spare solution, and the reaction was carried out for 2 hours. After addition, L-proline alcohol (0.43 g, 4.3 mmol) was added to the reaction solution, The reaction was carried out at room temperature for 4 hours.The reaction solution was poured into ice water, quenched and extracted twice with methylene chloride. The organic phase was combined and washed twice with water, dried over anhydrous sodium sulfate,The resulting crude column was concentrated to give 0.8 g of a white solid, i.e., avanafil, in 32percent yield
Reference: [1] Patent: CN104650045, 2017, B, . Location in patent: Paragraph 0100; 0103; 0104
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YieldReaction ConditionsOperation in experiment
8 g With triethylamine In dichloromethane To the dichioromethane layer obtained in step i), was added 2.57g of triethylamine followed by slow addition of l25m1 solution of L-prolinol in dichloromethane (2.46g of L-prolinol in l25m1 of dchlromethane). The reaction mixture was maintained overnight. After completion of reaction, the reaction mixture was washed with water followed by evaporation of dichioromethane to obtain an oily mass. The oily mass thus obtained was treated with methanol to yield 8g of Avanafil.
Reference: [1] Patent: WO2015/177807, 2015, A1, . Location in patent: Page/Page column 14; 16; 17
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