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[ CAS No. 89031-84-5 ] {[proInfo.proName]}

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Chemical Structure| 89031-84-5
Chemical Structure| 89031-84-5
Structure of 89031-84-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 89031-84-5 ]

CAS No. :89031-84-5 MDL No. :MFCD00216589
Formula : C9H21BrOSi Boiling Point : -
Linear Structure Formula :- InChI Key :QGMROEZDWJTIDW-UHFFFAOYSA-N
M.W : 253.25 Pubchem ID :607486
Synonyms :

Calculated chemistry of [ 89031-84-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 5
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 62.2
TPSA : 9.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.02 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.36
Log Po/w (XLOGP3) : 3.98
Log Po/w (WLOGP) : 3.79
Log Po/w (MLOGP) : 2.99
Log Po/w (SILICOS-IT) : 1.64
Consensus Log Po/w : 3.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.59
Solubility : 0.0655 mg/ml ; 0.000258 mol/l
Class : Soluble
Log S (Ali) : -3.88
Solubility : 0.0338 mg/ml ; 0.000133 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.78
Solubility : 0.042 mg/ml ; 0.000166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 4.64

Safety of [ 89031-84-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H227-H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89031-84-5 ]

* 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 [ 89031-84-5 ]
  • Downstream synthetic route of [ 89031-84-5 ]

[ 89031-84-5 ] Synthesis Path-Upstream   1~8

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YieldReaction ConditionsOperation in experiment
93% at 20℃; for 3 h; Inert atmosphere Example C: 3-(3-(2,5-Dioxo-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrol-3-yl)-1H-indol-1-yl)propyl 2-amino-4-methylpentanoate 3-Bromopropoxy-tert.-butyldimethylsilan A modified procedure of Galka et al. (J. Lab. Comp. Rad. 2005, 48(11): 797-809) was used to prepare the title compound. A mixture of 3-bromopropanol (39.1 mmole; 5.43 g), tert.-butyldimethylsilylchloride (43.2 mmole; 6.47 g) and imidazole (46.7 mmole; 3.20 g) was stirred at RT for 3 hours under inert gas. The reaction was quenched with water, extracted with diethylether, the organic layer dried over MgSO4, filtered and concentrated. The purification was achieved by column chromatography (PE) to yield the title compound (36.4 mmole; 93 percent). 1H NMR (300 MHz, CDCl3) 3.73 (t; 3J = 5.7 Hz; 2H; CH2O); 3.51 (t; 3J = 6.4 Hz; 2H; CH2Br); 2.02 (q; 3J = 5.7 Hz; 3J = 6.4 Hz; 2H; CH2CH2CH2); 0.89 (s; 9H; C(CH3)3); 0.06 (s; 6H; 2xCH3).
93% at 20℃; for 3 h; Inert atmosphere 3-Bromopropoxy-ferf.-butyldimethylsilanA modified procedure of Galka et al. (J. Lab. Comp. Rad. 2005, 48(11): 797-809) was used to prepare the title compound. A mixture of 3-bromopropanol (39.1 mmole; 5.43 g), te/t-butyldimethylsilylchloride (43.2 mmole; 6.47 g) and imidazole (46.7 mmole; 3.20 g) was stirred at RT for 3 hours under inert gas. The reaction was quenched with water, ex- tracted with diethylether, the organic layer dried over MgS04, filtered and concentrated. The purification was achieved by column chromatography (PE) to yield the title compound (36.4 mmole; 93 percent). 1 H NMR (300 MHz, CDCI3) 3.73 (t; 3J = 5.7 Hz; 2H; CH20); 3.51 (t; 3J = 6.4 Hz; 2H; CH2Br); 2.02 (q; 3J = 5.7 Hz; 3J = 6.4 Hz; 2H; CH?CH?CH?); 0.89 (s; 9H; C(CH3)3); 0.06 (s; 6H; 2xCH3).
81% With dmap; triethylamine In dichloromethane at 0 - 20℃; for 3 h; Inert atmosphere fresh 3-bromo-1-propanol (2 ml, 22.12 mmol) was dissolved in dry CH2Cl2 (8 ml). Triethylamine (3.39 ml, 24.33 mmol) and 4-(dimethylamino)pyridine (0.29 g, 2.433 mmol) were added under argon with stirring. The solution was cooled to 0 °C under argon, and t-butyldimethylsilyl chloride (3.33 g, 22.12 mmol) was added. The solution was allowed to come to room temperature while stirring for 3 h under argon (monitored by TLC using 15percent ethyl acetate/hexane with anisaldehyde detection). The reaction was quenched with water (5 ml) and allowed to stir for 15 min. The crude product was extracted from the aqueous solution with CH2Cl2, (3 * 10 ml). The combined organic extracts were dried over Na2SO4, filtered, and evaporated. Crude (3-bromopropoxy)-t-butyldimethylsilyl ether was purified on a silica gel column using 15percent ethyl acetate/hexane to yield 4.52 g, 17.85 mmol, 81percent yield, as a yellow oil. 1H NMR (CDCl3) d (ppm): 0.089 (s, 3H, SiCH3); 0.094 (s, 3H, SiCH3); 0.91 (s, 9H, t-Bu); 2.06 (m, 2H, BrCH2CH2CH2O); 3.53 (t, J = 5.7Hz, 2H, BrCH2CH2CH2O); 3.75 (t, J = 5.7 Hz, 2H, BrCH2CH2CH2O).
40% With 1H-imidazole In dichloromethane at 20℃; for 3 h; To lH-imidazole (13.4 g, 197 mmol) in DCM (100 mL) was added 3-bromopropan-l-ol (13.7 g, 99 mmol) followed slowly by fe/ butylchlorodimethylsilane (17.8 g, 118 mmol) in DCM (20 ml). After 3 hr at RT, the reaction was concentrated to ~100 mL and poured in EtOAc (800 mL), washed with 5percent aq citric acid (2 x 200 mL) and brine. The organic layer was dried over MgSCM, filtered and concentrated to yield the title compound (10.0 g, 39.5 mmol, 40 percent yield). *H NMR (400 MHz, chloroform-tf) δ ppm 3.78 (t, 7=5.70 Hz, 2 H), 3.56 (t, 7=6.46 Hz, 2 H), 2.07 (t, 7=5.83 Hz, 2 H), 0.94 (s, 9 H), 0.11 (s, 6 H).
28% With 1H-2,2,4-triazole In N,N-dimethyl-formamide at 25℃; for 12 h; Inert atmosphere Into a 500 ml round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed N,N-dimethylformamide (300 ml), 3-bromopropan-1-ol (30 g, 215.84 mmol, 1.21 equiv.), tert-butyl(chloro)dimethylsilane (26.8 g, 177.81 mmol, 1.00 equiv.), 4H- imidazole (36.4 g, 534.69 mmol, 3.01 equiv.). The resulting solution was stirred for 12 h at25 °C. The resulting solution was diluted with 500 ml of ethyl acetate. The resulting mixture was washed with 3x500 ml of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate. This resulted in 12.4 g of the title compound as colorless oil (28percent). ‘H NMR (300 MHz, CDC13) & 3.76-3.73 (m, 2H), 3.67-3.62 (m, 1H), 3.51 (t, 1=6.6Hz, 1H), 2.07-1.9 1 (m, 2H), 0.87 (s, 9H), 0.07 (s, 6H).

Reference: [1] Heterocycles, 2004, vol. 62, p. 423 - 436
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 14, p. 5080 - 5095
[3] Tetrahedron Letters, 2012, vol. 53, # 36, p. 4805 - 4808
[4] Journal of the American Chemical Society, 2012, vol. 134, # 43, p. 18101 - 18108
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 11, p. 797 - 809
[6] Journal of the American Chemical Society, 2001, vol. 123, # 1, p. 57 - 67
[7] Heterocycles, 1998, vol. 48, # 1, p. 79 - 93
[8] Chemistry - A European Journal, 2016, vol. 22, # 1, p. 116 - 119
[9] Synthetic Communications, 1992, vol. 22, # 2, p. 189 - 200
[10] Journal of Organic Chemistry, 1989, vol. 54, # 25, p. 5856 - 5866
[11] Patent: EP2474541, 2012, A1, . Location in patent: Page/Page column 16
[12] Patent: WO2012/84683, 2012, A1, . Location in patent: Page/Page column 23
[13] Journal of Medicinal Chemistry, 2009, vol. 52, # 1, p. 117 - 125
[14] Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 8-9, p. 520 - 528[15] Bioorganicheskaya Khimiya, 1994, vol. 20, # 8-9, p. 955 - 966
[16] ChemMedChem, 2011, vol. 6, # 10, p. 1816 - 1831
[17] Journal of Organic Chemistry, 1988, vol. 53, # 20, p. 4682 - 4693
[18] European Journal of Organic Chemistry, 2018, vol. 2018, # 23, p. 3017 - 3021
[19] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 10, p. 1570 - 1576
[20] Organic Letters, 2010, vol. 12, # 2, p. 336 - 339
[21] Journal of the American Chemical Society, 2004, vol. 126, # 28, p. 8606 - 8607
[22] Journal of Medicinal Chemistry, 1994, vol. 37, # 19, p. 3040 - 3050
[23] ChemMedChem, 2010, vol. 5, # 7, p. 1102 - 1109
[24] Journal of Biological Chemistry, 2018, vol. 293, # 8, p. 2949 - 2958
[25] Journal of Medicinal Chemistry, 1990, vol. 33, # 7, p. 1958 - 1962
[26] Bulletin de la Societe Chimique de France, 1988, # 6, p. 989 - 994
[27] Journal of Medicinal Chemistry, 1994, vol. 37, # 22, p. 3730 - 3738
[28] Organic Letters, 2001, vol. 3, # 25, p. 3987 - 3990
[29] Journal of Organic Chemistry, 1993, vol. 58, # 24, p. 6596 - 6608
[30] Journal of Organic Chemistry, 1996, vol. 61, # 12, p. 4120 - 4124
[31] Patent: WO2017/175147, 2017, A1, . Location in patent: Page/Page column 183; 184
[32] Patent: WO2016/44626, 2016, A1, . Location in patent: Paragraph 00505
[33] Journal of the American Chemical Society, 1994, vol. 116, # 20, p. 8952 - 8965
[34] Tetrahedron, 1998, vol. 54, # 27, p. 7907 - 7918
[35] Organic and Biomolecular Chemistry, 2005, vol. 3, # 2, p. 340 - 347
[36] Journal of Medicinal Chemistry, 2006, vol. 49, # 14, p. 4183 - 4195
[37] Patent: US5536713, 1996, A,
[38] Patent: EP2019103, 2009, A1, . Location in patent: Page/Page column 38
[39] Organic and Biomolecular Chemistry, 2008, vol. 6, # 12, p. 2168 - 2172
[40] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 2, p. 709 - 715
[41] Organic Letters, 2009, vol. 11, # 19, p. 4374 - 4377
[42] Journal of the American Chemical Society, 2010, vol. 132, # 29, p. 10024 - 10026
[43] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 213 - 216
[44] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11408 - 11411
[45] Helvetica Chimica Acta, 2016, vol. 99, # 7, p. 523 - 538
[46] Organic Letters, 2018, vol. 20, # 1, p. 119 - 121
[47] Patent: WO2018/97945, 2018, A1, . Location in patent: Paragraph 0291
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YieldReaction ConditionsOperation in experiment
92% With 1H-imidazole In dichloromethane at 20℃; for 0.166667 h; Cooling with ice 3-Bromopropanol (4.14 g, 30 mmol),Was added to DCM (50 mL), imidazole (2.5 g, 30 mmol) was added, stirred under ice for 10 min, TBDMS (4.5 g, 30 mmol) was added and the reaction was continued at room temperature. The next day, DCM (50 mL) (30 mL X3), dried over anhydrous magnesium sulfate and concentrated to give 7 g of a colorless oil in 92percent yield
Reference: [1] Patent: CN107098886, 2017, A, . Location in patent: Paragraph 0501; 0502
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Reference: [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 11, p. 2988 - 2992[2] Angew. Chem., 2014, vol. 53, # 11, p. 3
[3] Canadian Journal of Chemistry, 1988, vol. 66, p. 1794 - 1804
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  • [ 73842-99-6 ]
  • [ 89031-84-5 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1998, # 3, p. 614 - 634
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  • [ 288-32-4 ]
  • [ 18162-48-6 ]
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Reference: [1] Patent: US2001/41726, 2001, A1,
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  • [ 288-32-4 ]
  • [ 627-18-9 ]
  • [ 89031-84-5 ]
Reference: [1] Patent: EP2216050, 2010, A1,
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  • [ 288-32-4 ]
  • [ 18162-48-6 ]
  • [ 627-18-9 ]
  • [ 89031-84-5 ]
Reference: [1] Patent: US6297260, 2001, B1,
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Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 1794 - 1804
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