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Product Details of [ 5548-09-4 ]

CAS No. :5548-09-4 MDL No. :MFCD00022778
Formula : C12H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :BAYIDMGOQRXHBC-UHFFFAOYSA-N
M.W : 203.24 Pubchem ID :21711
Synonyms :

Safety of [ 5548-09-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 5548-09-4 ]

* 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.

  • Upstream synthesis route of [ 5548-09-4 ]
  • Downstream synthetic route of [ 5548-09-4 ]

[ 5548-09-4 ] Synthesis Path-Upstream   1~13

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Reference: [1] Collection of Czechoslovak Chemical Communications, 2002, vol. 67, # 11, p. 1669 - 1680
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  • [ 67-56-1 ]
  • [ 830-96-6 ]
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YieldReaction ConditionsOperation in experiment
96%
Stage #1: for 5 h; Reflux
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
EXAMPLE 2; N'-(3,4-dimethoxybenzylidene)-3-(l-methyl-lH-indol-3- yl)propanehydrazide; [0488] (a) Methyl 3-(lH-indol-3-yl)propanoate: To a stirred solution of 3- indolepropionic acid (5 g, 26.4 mmol) in MeOH (80 mL) was added cone. H2SO4 (0.5 mL). The reaction mixture was heated at reflux for 5 hours. The reaction mixture was allowed to cool to room temperature and the reaction solution was reduced to 1/3 volume at reduced pressure. The remaining solution was diluted with water and extracted with CH2Cl2. The organic phase was washed with saturated aq. NaHCO3 and brine and dried (Na2SO4). The material was purified on silica gel using EtOAc-hexanes (0 to 30percent) and provided 5.16 g (96percent) of the desired compound as a pale yellow oil which solidified upon standing.
95%
Stage #2: With hydrogenchloride In water
Example 2: Preparation of δ-lactam library 14.; [00181] A second generation indoline library with an expanded D-ring was prepared exploiting the intramolecular inverse electron demand Diels-Alder chemistry beginning with five N- alkylated indolylpropionic acids 8a-e and triazine 2. The indolylpropionic acids were prepared by straightforward pathways as shown in Scheme 2. For N-methylindolylpropionic13161987.4 64 acid 8a, permethylation of indolylpropionic acid, followed by basic methyl ester hydrolysis with acid work-up gave 8a in 87percent yield over three steps. For the remaining acids 8b-e, methyl ester 9 formation, then N-alkylation, followed by ester hydrolysis all proceeded uneventfully in good yields. With the five indolylpropionic acids in hand, the second sublibrary again formed through an intramolecular inverse electron demand Diels-Alder reaction of an indolyl subunit with a tethered triazine, was pursued (Scheme 3). Conversion of the propionic acids to the acid chlorides lOa-e, then amidation of 10 with aminotriazines derived from 2 produced the tethered diene/dieno-phile pairs 13. Intramolecularcycloadditions by heating to 120°C in 1,2-dichlorobenzene yielded sublibrary 14quantitatively. Twenty-two primary amines (Figure 3) were employed in the S Ar displacements on the chlorotriazine, producing 22 aminotriazines 12. All amidations and cycloadditions were accomplished smoothly, resulting in a 110-membered, racemic sublibrary 14; all members were stable to storage in DMSO. Figure 4 shows some exemplary compounds from the library. Compound 15-17, from this library, were found to be the most active in vitro inhibitors of core dimerization.Scheme 2: Pre aration of indolylpropionic acids 8Scheme 3: Preparation of δ-lactam sublibrary 14 (racemic)13161987.4 65
85% at 0℃; for 0.5 h; 3-(1H-indol-3-yl)propionic acid (200 mg, 1.06 mmol) was dissolved in anhydrous methanol (3 mL), and thionyl chloride (249 mg, 2.12 mmol) was added at 0°C to react for 0.5 h.
Water (10 mL) was added to quench the reaction.
The reaction solution was extracted with ethyl acetate (10 mL x 3).
The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure and purified by preparative TLC plate (3:1 petroleum ether / ethyl acetate, Rf = 0.5) to give methyl 3-(1H-indole-3)propionate (180 mg, as a green solid) with a yield of 85percent. MS-ESI [M + H]+ calcd. 204, found 204.
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 50, p. 7035 - 7037
[2] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 14, p. 4958 - 4979
[3] Patent: WO2010/132615, 2010, A1, . Location in patent: Page/Page column 100-101
[4] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6926 - 6930
[5] Patent: WO2011/56630, 2011, A2, . Location in patent: Page/Page column 64-65
[6] Collection of Czechoslovak Chemical Communications, 2002, vol. 67, # 11, p. 1669 - 1680
[7] Organic Letters, 2015, vol. 17, # 11, p. 2652 - 2655
[8] Patent: EP3299371, 2018, A1, . Location in patent: Paragraph 0314; 0315
[9] Farmaco, 2001, vol. 56, # 11, p. 835 - 840
[10] Tetrahedron Asymmetry, 2006, vol. 17, # 4, p. 521 - 535
[11] Patent: US2009/247573, 2009, A1, . Location in patent: Page/Page column 26-27
[12] Patent: US6352988, 2002, B2, . Location in patent: Page column 33-34
[13] Chemistry - A European Journal, 2014, vol. 20, # 24, p. 7492 - 7500
[14] Patent: WO2015/31608, 2015, A1, . Location in patent: Paragraph 00351
[15] Journal of Chemical Research, 2015, vol. 39, # 5, p. 296 - 299
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YieldReaction ConditionsOperation in experiment
93% With sulfuric acid In methanol at 0 - 20℃; 2 g (10.57 mmol) of 3-indolepropionic acid were dissolved in 50 ml of methanol. The solution was cooled to 0°C and 5 ml of sulfuric acid 96percent were dropped under stirring. The solution was maintained at room temperature overnight and then poured onto ice-water, basified with 30 percent ammonium hydrate and finally extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness to give 2.3 g of an oily product (93percent yield).
Reference: [1] Patent: EP1124810, 2005, B1, . Location in patent: Page/Page column 12
[2] Patent: US5464861, 1995, A,
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  • [ 830-96-6 ]
  • [ 74-88-4 ]
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Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 8, p. 1939 - 1957
[2] Patent: US5877199, 1999, A,
[3] Patent: WO2008/72784, 2008, A1, . Location in patent: Page/Page column 109
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Reference: [1] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 4, p. 977 - 986
[2] Journal of the Iranian Chemical Society, 2012, vol. 9, # 5, p. 655 - 660
[3] Chinese Journal of Chemistry, 2010, vol. 28, # 12, p. 2399 - 2403
[4] Tetrahedron Letters, 1988, vol. 29, # 21, p. 2577 - 2580
[5] Tetrahedron Letters, 2003, vol. 44, # 27, p. 5115 - 5119
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Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 5, p. 598 - 609
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Reference: [1] Organic Process Research and Development, 2001, vol. 5, # 6, p. 604 - 608
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Reference: [1] Synthesis, 1980, # 1, p. 68 - 70
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Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 4, p. 1128 - 1132
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Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 23, p. 2750 - 2753
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  • [ 16108-04-6 ]
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Reference: [1] Synthesis, 1980, # 1, p. 68 - 70
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Reference: [1] Synthesis, 1980, # 1, p. 68 - 70
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  • [ 161203-00-5 ]
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Reference: [1] Heterocycles, 1996, vol. 43, # 11, p. 2333 - 2342
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