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Product Details of [ 29124-57-0 ]

CAS No. :29124-57-0 MDL No. :MFCD10696879
Formula : C7H6BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :VBYZWJMZASVGNB-UHFFFAOYSA-N
M.W : 200.03 Pubchem ID :23510475
Synonyms :

Calculated chemistry of [ 29124-57-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.93
TPSA : 43.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.72 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.3
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 1.85
Log Po/w (MLOGP) : 1.55
Log Po/w (SILICOS-IT) : 1.94
Consensus Log Po/w : 1.83

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.05
Solubility : 0.177 mg/ml ; 0.000887 mol/l
Class : Soluble
Log S (Ali) : -3.08
Solubility : 0.166 mg/ml ; 0.000829 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.84
Solubility : 0.286 mg/ml ; 0.00143 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.19

Safety of [ 29124-57-0 ]

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 [ 29124-57-0 ]

* 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 [ 29124-57-0 ]
  • Downstream synthetic route of [ 29124-57-0 ]

[ 29124-57-0 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 123-42-2 ]
  • [ 29124-57-0 ]
  • [ 877-42-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 8966 - 8970
  • 2
  • [ 29124-57-0 ]
  • [ 39859-36-4 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 33, p. 9513 - 9515
  • 3
  • [ 20357-20-4 ]
  • [ 29124-57-0 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride; iron In ethanol; water at 80℃; for 4 h; 90 g of compound III (0.39 mmol) was added to a 1 L round bottom flask,To the system was added 300 ml of absolute ethanol,32 g of reduced iron powder (0.58 mol) was added under stirring,To the system was added 200 ml of 0.1 M HCl,Oil bath was heated to 80 ,The reaction was carried out for 4 hours,The substrate reaction was complete,A portion of the ethanol was removed by rotary evaporation,Solid precipitation,Filtration,The solid was slurried with methylene chloride to obtain 71 g of a pale yellow powder of Compound III,Yield 92percent.HPLC analysis showed a purity of 97percent No further purification was required for the next reaction.
Reference: [1] Synthesis, 2008, # 14 SPEC. ISS., p. 2199 - 2210
[2] Patent: CN105669566, 2016, A, . Location in patent: Paragraph 0032; 0033; 0034; 0035
[3] Organic Letters, 2003, vol. 5, # 13, p. 2251 - 2253
[4] Chemical Communications, 2011, vol. 47, # 33, p. 9513 - 9515
[5] Patent: WO2017/166104, 2017, A1, . Location in patent: Page/Page column 166
[6] Molecules, 2018, vol. 23, # 2,
  • 4
  • [ 20712-12-3 ]
  • [ 29124-57-0 ]
YieldReaction ConditionsOperation in experiment
76% With manganese(IV) oxide In dichloromethane at 20℃; for 3 h; 1L round bottom flask was charged with 1B (9.7 g, 48.0 mmol), manganese dioxide (29 g, 336 mmol), dichloromethane(400 mL), stirred at room temperature for 3 h and the reaction was complete by TLC. Suction filtered, washed with dichloromethane, the combined filtrate, the solvent was evaporated under reduced pressure,1C was obtained as a beige solid (7.3 g, 76.0percent yield).
71% With manganese dioxide In acetone REFERENCE EXAMPLE 286
To acetone (300 ml) were added (2-amino-5-bromophenyl)methanol (23.32 g) and active manganese dioxide (58.5 g), and the mixture was stirred at room temperature for 17.5 hours and filtered.
The solvent was evaporated under reduced pressure to give 2-amino-5-bromobenzaldehyde (16.41 g, 71percent).
1 H NMR (200 MHz, CDCl3) δ 6.10-6.20 (2H, br), 6.57 (1H, d, J=8.8 Hz), 7.38 (1H, dd, J=8.8, 2.4 Hz), 7.59 (1H, d, J=2.4 Hz), 9.81 (1H, s).
8 g With manganese(IV) oxide In dichloromethane at 20℃; Step 2: Synthesis of 2-amino-5-bromobenzaldehyde A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and Mn02 (25.8 g, 296.6 mmol) in CH2C12 (400 mL) was stuffed at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the titlecompound as a light yellow solid (8 g, 8 1percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M + H].
8 g With manganese(IV) oxide In dichloromethane at 20℃; A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO2 (25.8 g, 296.6 mmol) in CH2Cl2 (400 mL) was stirred at RT overnight. LCMS showed the reaction was completed.
The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (8 g, 81percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M+H]+.
8 g With manganese(IV) oxide In dichloromethane at 20℃; A mixture of (2-amino-5-bromophenyl)methanol (10 g, 49.5 mmol) and MnO2 (25.8 g, 296.6 mmol) in CH2Cl2 (400 mL) was stirred at RT overnight. LCMS showed the reaction was completed. The solid was filtered off, and the filtrate was concentrated to give the title compound as a light yellow solid (8 g, 81percent), which was directly used in next step without further purification. MS (ES+) C7H6BrNO requires: 199, found: 200, 202 [M+H]+.

Reference: [1] Organic Syntheses, 2013, vol. 90, p. 240 - 250
[2] ChemistryOpen, 2015, vol. 4, # 2, p. 107 - 110
[3] Patent: CN107304201, 2017, A, . Location in patent: Paragraph 0061; 0065
[4] Patent: US6166006, 2000, A,
[5] Journal of Organic Chemistry, 2010, vol. 75, # 4, p. 1188 - 1196
[6] Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5530 - 5535
[7] Patent: WO2014/11900, 2014, A2, . Location in patent: Page/Page column 37; 38
[8] Patent: US2015/197519, 2015, A1, . Location in patent: Paragraph 0127; 0128
[9] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2191 - 2195
[10] Patent: US9695165, 2017, B2, . Location in patent: Page/Page column 38
[11] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
  • 5
  • [ 5551-12-2 ]
  • [ 29124-57-0 ]
Reference: [1] Patent: WO2010/48582, 2010, A1, . Location in patent: Page/Page column 179
  • 6
  • [ 529-23-7 ]
  • [ 29124-57-0 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 6, p. 1119 - 1123
[2] Patent: WO2004/18461, 2004, A2, . Location in patent: Page 26-27
[3] Inorganic Chemistry, 2016, vol. 55, # 22, p. 11908 - 11919
  • 7
  • [ 5794-88-7 ]
  • [ 29124-57-0 ]
Reference: [1] Chemistry - A European Journal, 2012, vol. 18, # 18, p. 5530 - 5535
[2] Patent: WO2014/11900, 2014, A2,
[3] Patent: US2015/197519, 2015, A1,
[4] Advanced Synthesis and Catalysis, 2017, vol. 359, # 13, p. 2191 - 2195
[5] Patent: US9695165, 2017, B2,
[6] Organic and Biomolecular Chemistry, 2017, vol. 15, # 31, p. 6474 - 6477
[7] Patent: CN107304201, 2017, A,
  • 8
  • [ 52727-57-8 ]
  • [ 29124-57-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5836 - 5857
  • 9
  • [ 68-12-2 ]
  • [ 106-40-1 ]
  • [ 29124-57-0 ]
Reference: [1] Heterocyclic Communications, 2006, vol. 12, # 6, p. 481 - 484
  • 10
  • [ 3132-99-8 ]
  • [ 29124-57-0 ]
Reference: [1] Patent: CN105669566, 2016, A,
  • 11
  • [ 420-04-2 ]
  • [ 29124-57-0 ]
  • [ 190273-89-3 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With hydrogenchloride In diethyl ether; water for 0.0833333 h;
Stage #2: at 80℃; for 12 h;
70 g of compound IV (0.35 mmol) was added to a 500 ml beaker,Followed by adding 250ml of ether,25ml of 37percent hydrochloric acid for 5 minutes,Filtration,The solid was added to a 500 ml round bottom flask,29 g of cyanamide (0.70 mol) was added,60 ml of N, N-dimethylformamide was added and the oil bath was heated to 80 ° C,TLC monitoring,The reaction was complete after 12 hours,Cooling the reaction system,300 ml of water was added,Filtration,Solid ethyl acetateAnd recrystallized from n-hexane to give the product,Filtered to obtain 56 g of a pale yellow powder of Compound V,Yield 72percent.
Reference: [1] Patent: CN105669566, 2016, A, . Location in patent: Paragraph 0036; 0037; 0038; 0039; 0040; 0041
  • 12
  • [ 29124-57-0 ]
  • [ 882672-05-1 ]
Reference: [1] Patent: WO2014/11900, 2014, A2,
[2] Patent: US2015/197519, 2015, A1,
[3] Patent: US9695165, 2017, B2,
[4] Patent: CN107304201, 2017, A,
  • 13
  • [ 29124-57-0 ]
  • [ 1196155-68-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5836 - 5857
[2] Patent: US2012/94976, 2012, A1,
  • 14
  • [ 1001-26-9 ]
  • [ 29124-57-0 ]
  • [ 1220418-77-8 ]
YieldReaction ConditionsOperation in experiment
51% With hydrogenchloride In methanol; water at 100℃; for 4 h; Method of Synthesising Quinoline D.57Ethoxyacrylate ED.13 (6.4 mL, 44.3 mmol) is placed in MeOH (120 mL), combined with HCl (88 mL, 2M in H2O) and heated to 100° C. Benzaldehyde ED.12 (4.00 g, 20.1 mmol) is placed in MeOH (120 mL), slowly added dropwise to the reaction mixture and the reaction mixture is heated to 100° C. for 4 h. Then it is made basic with NaHCO3, the solvent is eliminated, the residue is purified by chromatography (90:10 to 40:60 in 15 min hexane/EtOAc) and quinoline D.57 (4.08 g, 51percent; HPLC-MS: MS (M+H)+=266/268; tRet=1.50 min; method LCMSBAS1) is obtained.
Reference: [1] Patent: US2012/94976, 2012, A1, . Location in patent: Page/Page column 57
  • 15
  • [ 67-56-1 ]
  • [ 1001-26-9 ]
  • [ 29124-57-0 ]
  • [ 1220418-77-8 ]
YieldReaction ConditionsOperation in experiment
51% With hydrogenchloride In water at 100℃; for 4 h; Method of synthesising quinoline D.57Ethoxyacrylate ED.13 (6.4 mL, 44.3 mmol) is placed in MeOH (120 mL), combined with HCI (88 mL, 2M in H20) and heated to 100°C. Benzaldehyde ED.12 (4.00 g, 20.1 mmol) is placed in MeOH (120 mL), slowly added dropwise to the reaction mixture and the reaction mixture is heated to 100°C for 4 h. Then it is made basic with NaHC03, the solvent is eliminated, the residue is purified by chromatography (90:10 to 40:60 in 15 min hexane/EtOAc) and quinoline D.57 (4.08 g, 51 percent; HPLC-MS: MS(M+H)+ = 266/268; tRet = 1 .50 min; method LCMSBAS1 ) is obtained.
Reference: [1] Patent: WO2011/131741, 2011, A1, . Location in patent: Page/Page column 90
  • 16
  • [ 7424-91-1 ]
  • [ 29124-57-0 ]
  • [ 1220418-77-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2011, vol. 54, # 16, p. 5836 - 5857
  • 17
  • [ 29124-57-0 ]
  • [ 1538604-68-0 ]
Reference: [1] Patent: WO2014/11900, 2014, A2,
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