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Chemical Structure| 67567-26-4
Chemical Structure| 67567-26-4
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Product Details of [ 67567-26-4 ]

CAS No. :67567-26-4 MDL No. :MFCD00013389
Formula : C6H4BrF2N Boiling Point : -
Linear Structure Formula :- InChI Key :BFQSQUAVMNHOEF-UHFFFAOYSA-N
M.W : 208.00 Pubchem ID :610191
Synonyms :

Calculated chemistry of [ 67567-26-4 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.46
TPSA : 26.02 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) : -6.06 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 2.13
Log Po/w (WLOGP) : 3.16
Log Po/w (MLOGP) : 3.1
Log Po/w (SILICOS-IT) : 2.66
Consensus Log Po/w : 2.57

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.253 mg/ml ; 0.00121 mol/l
Class : Soluble
Log S (Ali) : -2.31
Solubility : 1.02 mg/ml ; 0.00492 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.46
Solubility : 0.073 mg/ml ; 0.000351 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.4

Safety of [ 67567-26-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67567-26-4 ]

* 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 [ 67567-26-4 ]
  • Downstream synthetic route of [ 67567-26-4 ]

[ 67567-26-4 ] Synthesis Path-Upstream   1~18

  • 1
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  • [ 147808-42-2 ]
YieldReaction ConditionsOperation in experiment
68%
Stage #1: With sodium perborate In acetic acid at 65 - 70℃; for 72 h; Heating / reflux
Stage #2: at 0℃;
To a suspension of sodium perborate tetrahydrate (1.78 mmol, 0.27 g) in 10 ml of acetic acid stirred at 650C was added a solution of (4-bromo-2,6-difluorophenyl)amine (1.78 mmol, 0.42 g, 1 eq.) in 5 ml of acetic acid over one hour dropwise. The reaction was heated at 650C over 3 days. Sodium perborate tetrahydrate (2 eq., 3.56 mmol, 0.54 g) was added again. After 3 hours, sodium perborate tetrahydrate (1eq., 1.78 mmol, 0.27 g) was added again. Additional sodium perborate tetrahydrate (3eq., 5.34 mmol, 0.81 g) was again added. The reaction was then left overnight at 7O0C under reflux and under argon. The solution was then cooled to room temperature and poured onto ice and extracted with ethyl acetate (2x). The combined organics were washed with water and brine. The organics were dried over MgSO4, filtered and the organic solvent was removed under reduced pressure to afford the crude product which was purified by silica chromatography (ethyl acetate-4percent n-hexane 96percent) to afford the title compound, 0.29 g, 68percent. 1H NMR δ (d6DMSO, 400MHz): 7.964 (2H, d)
60% at 65℃; Sodiumperborate tetrahydrate (18.5 g, 0.12 mol, 5.0 eq) was suspended in glacial acetic acid (125 mL) and heated to 65 °C. 4-Bromo-2,6-difluoroanilline 2 (5.0 g, 24.0 mmol, 1.0 eq) dissolved in glacial acetic acid (50 mL) was added slowly through an funnel over 4 h. After the addition the reaction mixture was heated for 3 h additional hours before a second portion of NaBO3·4H2O (6.0 g, 30.0 mmol) was added. Then the mixture was stirred for 14 h and a third portion of oxidating agent (9.0 g, 45.0 mmol) was added. 9 h after the third addition full consumption of the starting material was indicated by TLC. After cooling the mixture to room temperature, the formed solid was removed by filtration. The filtrate was poured into ice-cold water (300 mL). The precipitated solid was filtered off and dried to give the product as yellow solid (3.40 g, 60percent). TLC [Silica, hexane/CHCl3 (5:1)]: Rf = 0.31. 1H NMR (300 MHz, CDCl3): δ = 7.36-7.28 (m, 2H). 13C NMR (75 MHz, CDCl3): δ = 154.7 (dd, J = 265.7, 2.8 Hz), 126.4 (t, J = 11.0 Hz), 117.2 (dd, J = 22.7, 3.9 Hz), [C-NO2 is not detected]. 19F NMR (282 MHz, CDCl3): δ = -117.0 (d, J = 7.1 Hz). LRMS (EI): m/z = 237 (calcd. 237 for C6H2 79BrF2NO2 [M]+).
47% With sulfuric acid; dihydrogen peroxide; acetic acid In water at 85℃; for 1 h; Compound 121 : 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9- tetrahydro-5H-pyrimido[4,5-b][l,4]diazepin-2-ylamino)-3-fluoro-5-methoxybenzoic acid; [0581] 5-Bromo-l,3-difluoro-2-nitrobenzene: To a mixture of acetic acid (30 mL), 30percent H2O2 (20 mL) and concentrated sulfuric acid (1 mL) was added l-bromo-2,6- difluoroaniline (5 g, 24 mmol) in acetic acid (10 mL) dropwise at 85 0C. The reaction mixture was heated for 1 h. It was then cooled down, diluted to water and extracted with ethyl acetate. The organic layer was dried and concentrated to a red residue, which was purified by flash column (EtOAc in Hexane 2-5percent) to give the product as yellow solid (2.7 g, 47percent). 1H NMR (400 MHz, CHLOROFORM-J) δ ppm 7.33 (m, 2 H).
42% With sulfuric acid; dihydrogen peroxide; acetic acid In water at 85℃; for 1 h; EXAMPLE 21; Preparation of Methyl [(2S)- 1 - {(25}-2-[5-(5- {2-[(25)- 1 - { (2.pound.)-2-[(methoxycarbonyl)amino]-3 - methyl butanoyl}pyrrolidin-2-yl]-lH-imidazol-5-yl}- l ,2-dihydro[l ,4]oxazino[2,3,4-W] phenoxazin- 10-yl)-lH-imidazol-2-yl]pyrrolidin- 1 -yl } -3-methyl- 1 -oxobutan-2-yl] carbamate(Compound 13); Step A - Synthesis of Compound Int-21a; To a solution of compound 4-bromo-2,6-difluoroaniIine (20 g, 0.1 mol) in acetic acid (120 mL) was added 30percent Η202 (80 mL) and concentrated sulfuric acid (4 mL). The reaction mixture was heated to 85 °C and allowed to stir at this temperature for 1 hour, then was cooled to room temperature and partitioned between EtOAc and water. The organic phase was separated and concentrated in vacuo. The residue obtained was purified using chromatography on silica gel [petroleum ether / EtOAc (gradient: 50/1 - 5/1)] to provide compound Int-21a ( 10.0 g, 42percent). NMR: (CDC.3) δ: 7.31 -7.29 (d, J=7.6 Hz, 2 H).
42% With sulfuric acid; dihydrogen peroxide In water; acetic acid at 85℃; for 1 h; Synthesis of Compound Int-21aInt 21aTo a solution of compound 4-bromo-2,6-difluoroaniline (20 g, 0.1 mol) in acetic acid (120 mL) was added 30percent H202 (80 mL) and concentrated sulfuric acid (4 mL). The reaction mixture was heated to 85 °C and allowed to stir at this temperature for 1 hour, then was cooled to room temperature and partitioned between EtOAc and water. The organic phase was separated and concentrated in vacuo. The residue obtained was purified using chromatography on silica gel [petroleum ether / EtOAc (gradient: 50/1 - 5/1)] to provide compound Int-21a (10.0 g, 42percent). 1H MR: (CDC13) δ: 7.31-7.29 (d, J=7.6 Hz, 2 H).

Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3364 - 3386
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 23, p. 6686 - 6690
[3] Patent: WO2007/36715, 2007, A2, . Location in patent: Page/Page column 51
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 17, p. 5243 - 5263
[5] European Journal of Medicinal Chemistry, 2016, vol. 107, p. 97 - 108
[6] Patent: WO2009/42711, 2009, A1, . Location in patent: Page/Page column 364
[7] Patent: WO2012/125926, 2012, A2, . Location in patent: Page/Page column 75
[8] Patent: WO2012/122716, 2012, A1, . Location in patent: Page/Page column 94
[9] Patent: US2004/235886, 2004, A1, . Location in patent: Page 68-69
[10] Patent: US2005/38247, 2005, A1,
[11] Patent: US2005/256136, 2005, A1,
[12] Patent: WO2010/24903, 2010, A1, . Location in patent: Page/Page column 96
[13] Patent: US2015/203455, 2015, A1, . Location in patent: Paragraph 0421-0422
[14] Patent: WO2015/110378, 2015, A1, . Location in patent: Paragraph 00237
[15] Patent: US9440929, 2016, B2, . Location in patent: Page/Page column 51; 52
  • 2
  • [ 5509-65-9 ]
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YieldReaction ConditionsOperation in experiment
92%
Stage #1: With bromine; acetic acid In water at 20℃; for 0.25 h;
Stage #2: With sodium carbonate In water
b) Preparation of intermediate 2; 2,6-difluorobenzeneamine (3.0g, 22.56 mmoles) was dissolved in acetic acid (10 ml). Bromine (1.2 ml) was added to the solution. The mixture was stirred for 15 minutes at room temperature. After evaporation of the solvent, the residue was treated with an aqueous solution of sodium carbonate. The aqueous solution was extracted with dichloromethane. The organic extract was dried over MgSC>4 and was evaporated. Yield : 92percent of intermediate 2.
91.7% With bromine In ice-water; acetic acid 1a)
507.5 g of 2,6-difluoroaniline are added to 2500 ml of acetic acid, the mixture is cooled to 10° C., and a solution of 195 ml of bromine in 250 ml of acetic acid is added dropwise at 10-15° C. over the course of 3 hours.
The mixture is subsequently stirred at room temperature for a further 1 hour and poured into 5000 ml of ice-water, the precipitated crystals are filtered off with suction and washed a number of times with a total of 3000 ml of ice-water, and the crystals are dried over Al2O3 under reduced pressure, giving 4-bromo-2,6-difluoroaniline, yield 91.7percent, GC 99.6percent.
84% at 20℃; for 2 h; Cooling with ice 2,6-Difluoroaniline (20.0 g, 0.15 mol, 1.0 eq) was dissolved in of glacial acetic acid (70 mL). The mixture was cooled with an ice bath and bromine (27.6 g, 0.16 mol, 1.1 eq) dissolved in acetic acid (10 mL) was added dropwise. During the addition the product precipitated. After stirring for 2 h at room temperature Na2SO3-solution (1.3 g Na2SO3 in 400 mL water) was added. The product was filtered off, washed with water and dried to afford a colorless solid (27.7 g, 84percent). TLC [Silica, DCM]: Rf = 0.71. 1H NMR (300 MHz, CDCl3): δ = 7.08-6.89 (m, 2H), 3.73 (s, 2H). 13C NMR (75 MHz, CDCl3): δ = 151.9 (dd, J = 244.1, 8.6 Hz), 123.6 (t, J = 16.2 Hz), 115.1-114.6 (m), 107.2 (t, J = 11.7 Hz). 19F NMR (282 MHz, CDCl3): δ = 131.1 (d, J = 7.1 Hz). LRMS (ESI): m/z 207.9 (calcd. 208.0 for C6H579BrF2N [M+H]+).
80.7% With N-Bromosuccinimide In dichloromethane at 20℃; for 3 h; To a solution of 2,6-difluoroaniline (1 g, 7.75 mmol) in 20 mL of dry DCM was added NBS (1.96 g, 9.29mmol). The mixture was stirred at room temperature for 3 hours. The mixture was filtered andconcentrated under reduced pressure. The residue was purified by column chromatography on silica gel (PE/EA = 50/1 to 20/1) to afford the title compound (1.61 g, 80.7percent yield) as a yellow solid. LCMS (ESI) calc’d for C6H4BrF2N [M+H]: 208, found: 208.
62% With N-Bromosuccinimide In <i>N</i>-methyl-acetamide (i)
Preparation of 1-(4'-amino-3',5'-difluorobenzyl)imidazole-2-thiol-4-bromo-2,6-difluoroaniline
Fifty grams (0.39 mole) of 2,6-difluoroaniline was treated with 71.0 g (0.39 mole) of N-bromosuccinimide in 250 ml of dimethylformamide by the procedure of Mitchell, Lai and Williams, J. Org. Chem., 44, 4733 (1979) to give a total yield of 50.2 g (62percent) of 4-bromo-2,6-difluoroaniline, m.p.: 64°-66° C.

Reference: [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 4, p. 1544 - 1547[2] Angew. Chem., 2016, vol. 128, # 4, p. 1569 - 1573,5
[3] Journal of Materials Chemistry C, 2016, vol. 4, # 23, p. 5326 - 5333
[4] Patent: WO2006/15985, 2006, A1, . Location in patent: Page/Page column 54
[5] Patent: US6716491, 2004, B2,
[6] Agricultural and Biological Chemistry, 1984, vol. 48, # 11, p. 2883 - 2888
[7] European Journal of Medicinal Chemistry, 2016, vol. 107, p. 97 - 108
[8] Journal of Medicinal Chemistry, 2011, vol. 54, # 3, p. 751 - 764
[9] Journal of the American Chemical Society, 2012, vol. 134, # 51, p. 20597 - 20600
[10] Patent: WO2014/28589, 2014, A2, . Location in patent: Page/Page column 79
[11] Molecular Crystals and Liquid Crystals (1969-1991), 1989, vol. 172, p. 165 - 190
[12] Journal of Chemical Research, 2004, # 10, p. 699 - 701
[13] Patent: US5354502, 1994, A,
[14] Patent: US5030382, 1991, A,
[15] Patent: US4719223, 1988, A,
[16] Patent: US4883609, 1989, A,
[17] Journal of Chemical Research, 2011, vol. 35, # 3, p. 151 - 153
[18] Patent: WO2012/97682, 2012, A1, . Location in patent: Page/Page column 107
[19] Patent: WO2012/97684, 2012, A1, . Location in patent: Page/Page column 70-71
[20] Angewandte Chemie - International Edition, 2017, vol. 56, # 12, p. 3349 - 3353[21] Angew. Chem., 2017, vol. 129, p. 3397 - 3401,5
  • 3
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Reference: [1] Patent: US5200110, 1993, A,
  • 4
  • [ 151-50-8 ]
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  • [ 123843-67-4 ]
Reference: [1] Molecular Crystals and Liquid Crystals (1969-1991), 1989, vol. 172, p. 165 - 190
  • 5
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  • [ 123688-59-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 17, p. 5235 - 5246
  • 6
  • [ 67567-26-4 ]
  • [ 110301-23-0 ]
YieldReaction ConditionsOperation in experiment
86% for 1.5 h; Reflux A mixture suspension of 4-bromo-2,6-difluoroaniline (7, 25.85 g) and copper(I) cyanide (16.70 g) in NMP (60 mL) was stirred at reflux temperature for 1.5 h and then cooled down to room temperature. To the mixture was added 1,2-diaminoethane (23 mL) and the mixture was poured into water (150 mL). The mixture was extracted with ethyl acetate and the organic layer was washed with 10 wt percent 1,2-diaminoethane solution in water and water, and then dried. The desiccant was removed by filtration and the filtrate was evaporated in vacuo. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 8 (16.54 g, 86percent) as a pale yellow solid: 1H NMR (DMSO-d6) δ 6.36 (2H, s), 7.50 (2H, dd, J = 2.7, 6.7 Hz); EI-MS m/z 154 [(M)+].
Reference: [1] Journal of Materials Chemistry C, 2016, vol. 4, # 23, p. 5326 - 5333
[2] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 17, p. 5235 - 5246
[3] Journal of the American Chemical Society, 2012, vol. 134, # 51, p. 20597 - 20600
[4] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 3, p. 250 - 255
[5] Patent: WO2018/136935, 2018, A1, . Location in patent: Paragraph 00407
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Reference: [1] Patent: US5354502, 1994, A,
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  • [ 110301-23-0 ]
Reference: [1] Patent: US5030382, 1991, A,
  • 9
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  • [ 110301-23-0 ]
Reference: [1] Bioconjugate Chemistry, 2018, vol. 29, # 2, p. 324 - 334
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  • [ 1123172-89-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3364 - 3386
  • 11
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  • [ 1123172-88-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3364 - 3386
  • 12
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  • [ 500577-99-1 ]
Reference: [1] Bioconjugate Chemistry, 2018, vol. 29, # 2, p. 324 - 334
[2] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 3, p. 250 - 255
[3] Patent: WO2018/136935, 2018, A1,
  • 13
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Reference: [1] Patent: WO2009/55331, 2009, A2, . Location in patent: Page/Page column 199
  • 14
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  • [ 1231930-33-8 ]
Reference: [1] Patent: WO2015/130540, 2015, A1,
[2] Patent: CN107827875, 2018, A,
  • 15
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  • [ 1231930-37-2 ]
Reference: [1] Patent: WO2015/130540, 2015, A1,
[2] Patent: CN107827875, 2018, A,
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Reference: [1] Patent: WO2015/130540, 2015, A1,
[2] Patent: CN107827875, 2018, A,
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Reference: [1] Patent: WO2015/130540, 2015, A1,
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  • [ 201230-82-2 ]
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  • [ 1415920-00-1 ]
YieldReaction ConditionsOperation in experiment
10% at 80℃; for 24 h; To a solution of 4-bromo-2,6-difluoroaniline (i-27a) (10 g, 48.1 mmol) in EtOH (100 mL) was added Et3N (14.6 g, 144 mmol) and Pd(dppf)C12 (1 g). The mixture was stirred at 80 °C for 24 hours under CO (2 MPa) atmosphere, after which LCMS showed 15 percent conversion. The resulting mixture was filtered and concentrated. The residue was purified by column chromatography on silica gel (PE/EA=50: 1 to 40:1) to afford the title compound (1 g, 10 percent yield). LCMS (ESI) calc’d for C9H9F2N02 [M+H]: 202, found: 202.
Reference: [1] Patent: WO2014/28589, 2014, A2, . Location in patent: Page/Page column 79; 80
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