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[ CAS No. 67344-77-8 ] {[proInfo.proName]}

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Chemical Structure| 67344-77-8
Chemical Structure| 67344-77-8
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Product Details of [ 67344-77-8 ]

CAS No. :67344-77-8 MDL No. :MFCD04507522
Formula : C8H10BrN Boiling Point : -
Linear Structure Formula :- InChI Key :QCEANFBGRBLXHN-UHFFFAOYSA-N
M.W : 200.08 Pubchem ID :457588
Synonyms :

Calculated chemistry of [ 67344-77-8 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.72
TPSA : 12.03 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) : -9.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : -3.26
Log Po/w (WLOGP) : 2.02
Log Po/w (MLOGP) : 2.61
Log Po/w (SILICOS-IT) : 2.51
Consensus Log Po/w : 1.24

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.66
Solubility : 917.0 mg/ml ; 4.58 mol/l
Class : Highly soluble
Log S (Ali) : 3.58
Solubility : 759000.0 mg/ml ; 3790.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -4.1
Solubility : 0.016 mg/ml ; 0.0000798 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 67344-77-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 67344-77-8 ]

* 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 [ 67344-77-8 ]
  • Downstream synthetic route of [ 67344-77-8 ]

[ 67344-77-8 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 3132-99-8 ]
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YieldReaction ConditionsOperation in experiment
81% With sodium tetrahydroborate In methanol; water at 0 - 20℃; for 3.5 h; Step B: To a solution of 3-bromobenzaldehyde (47.5 mL, 0.4 mol) in methanol (460 mL) at room temperature was added a solution of methylamine in water (35 mL, 0.4 mol, 40 wt. percent solution). The resultant solution was cooled to 0° C. and sodium borohydride (22 g, 0.6 mol) was added to it in portions. The reaction solution was stirred at 0° C. for 3 hours and 30 minutes, and then warmed to room temperature. The resultant reaction mixture was concentrated in vacuo and partitioned between dichloromethane and water. The aqueous layer was separated and washed with dichloromethane (3.x.). The combined organic extract was washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give the desired benzylamine (76 g, 81percent) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.48 (d, J=1.5 Hz, 1H), 7.40-7.37 (m, 1H), 7.24-7.16 (m, 2H), 3.73 (s, 2H), 2.45 (s, 3H).; Example 81 Preparation of (+)-N-methyl-2-(2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)ethanesulfonamide, L-tartrate salt and (-)-N-methyl-2-(2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepin-8-yl)ethanesulfonamide, L-tartrate salt Step A: To a solution of 3-bromobenzaldehyde (47.5 mL, 0.4 mol) in methanol (460 mL) at room temperature was added a solution of methylamine in water (35 mL, 0.4 mol, 40 wt percent solution). The resultant solution was cooled to 0° C. and sodium borohydride (22 g, 0.60 mol) was added to it in portions. The reaction solution was stirred at 0° C. for 3 hours and 30 minutes, and then warmed to room temperature. The resultant reaction mixture was concentrated in vacuo and partitioned between dichloromethane and water. The aqueous layer was separated and washed with dichloromethane (3.x.). The combined organic extracts were washed with saturated sodium bicarbonate and brine, dried over magnesium sulfate, filtered and concentrated in vacuo to give the benzylamine (76 g, 81percent) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.48 (d, J=1.5 Hz, 1H), 7.40-7.37 (m, 1H), 7.24-7.16 (m, 2H), 3.73 (s, 2H), 2.45 (s, 3H).
Reference: [1] Patent: US2007/21408, 2007, A1, . Location in patent: Page/Page column 94; 103
[2] Journal of Medicinal Chemistry, 1981, vol. 24, # 2, p. 140 - 145
[3] Patent: WO2009/149258, 2009, A2, . Location in patent: Page/Page column 21; 48
[4] Patent: US2014/275101, 2014, A1, . Location in patent: Paragraph 0072; 0145; 0146
[5] Patent: WO2015/127559, 2015, A1, . Location in patent: Page/Page column 55; 56
[6] Patent: WO2008/141082, 2008, A1, . Location in patent: Page/Page column 67-68; 77; 80; 83-84; 90
  • 2
  • [ 24424-99-5 ]
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  • [ 67344-77-8 ]
YieldReaction ConditionsOperation in experiment
59%
Stage #1: With sodium hydroxide In tetrahydrofuran at 20℃; for 0.0833333 h;
Stage #2: for 0.5 h;
Stage #3: With lithium aluminium tetrahydride In ethyl acetate at 100℃; for 1 h; Microwave irradiation
Example 95
1-(3-Bromophenyl)-N-methylmethanamine
To bromobenzylamine (0.890 g, 4 mmol) in THF (9 mL) was added NaOH (4.20 mL, 1 N, 4.20 mmol) and the solution was stirred at room temperature for 5 mins, when BOC2O (0.975 mL, 4.20 mmol) was added.
This mixture was stirred for an additional 30 mins.
The reaction mixture was diluted with EtOAc (20 mL).
The organic layer was separated, washed with brine (5 mL), dried over Na2SO4, filtered and concentrated.
Lithium aluminum hydride (12.00 mL, 12.00 mmol) was added to the above crude product and heated in a microwave at about 100° C. for about 1 h.
The reaction mixture was diluted with Et2O (~50 mL) and quenched slowly with Na2SO4 (sat.).
The organic layer was separated, dried over, filtered, and concentrated to afford the title compound (0.472 g, 59percent). LC-MS m/z 200 (M+H)+.
Reference: [1] Patent: US2009/203677, 2009, A1, . Location in patent: Page/Page column 72; 73
  • 3
  • [ 171663-13-1 ]
  • [ 67344-77-8 ]
Reference: [1] Patent: US2009/203657, 2009, A1, . Location in patent: Page/Page column 69
[2] Patent: US2009/197871, 2009, A1, . Location in patent: Page/Page column 103
[3] Patent: WO2009/100169, 2009, A1, . Location in patent: Page/Page column 159
  • 4
  • [ 823-78-9 ]
  • [ 67344-77-8 ]
YieldReaction ConditionsOperation in experiment
63.2% With hydrogenchloride; triethylamine In methanol; methylamine Referential Example 3
Production of N-(3-Bromobenzyl)methylamine
Triethylamine (19.2 g; 100.5 mmol) was dissolved in 40percent solution of methylamine in methanol (150 ml).
While the resultant solution was stirred in an ice bath, a solution of 3-bromobenzylbromide (25.1 g; 100.5 mmol) in methanol (40 ml) was added dropwise.
After completion of the addition, the mixture was removed from the ice bath, and stirred for 15 hours at room temperature.
Methanol and excess methylamine were evaporated under reduced pressure, and the residue was taken up in a mixture of ether and 2N hydrochloric acid (100 ml-100 ml).
The aqueous layer was alkalinized with aqueous sodium hydroxide solution, and the mixture was extracted with chloroform (100 ml).
The organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine, and dried over anhydrous sodium sulfate.
The solvent was evaporated under reduced pressure, to thereby yield 12.7 g of the target compound as a yellow-orange oily substance (yield: 63.2percent).
1H-NMR (CDCl3, ppm); 2.44 (3H, s), 3.72 (2H, s), 7.16~7.26 (2H, m), 7.38 (1H, m), 7.49 (1H, s).
Reference: [1] Patent: US6586633, 2003, B1,
  • 5
  • [ 823-78-9 ]
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  • [ 67344-77-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 1, p. 40 - 44
[2] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
  • 6
  • [ 317358-61-5 ]
  • [ 67344-77-8 ]
Reference: [1] Patent: US2004/39038, 2004, A1,
  • 7
  • [ 3132-99-8 ]
  • [ 593-51-1 ]
  • [ 67344-77-8 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1987, vol. 320, # 7, p. 647 - 654
[2] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 16, p. 2527 - 2531
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 3, p. 972 - 986
  • 8
  • [ 35003-56-6 ]
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Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1111 - 1118
  • 9
  • [ 3132-99-8 ]
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Reference: [1] Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1111 - 1118
  • 10
  • [ 10269-01-9 ]
  • [ 67344-77-8 ]
Reference: [1] Chemical Research in Toxicology, 1997, vol. 10, # 1, p. 19 - 26
[2] Patent: WO2009/100169, 2009, A1,
  • 11
  • [ 74-89-5 ]
  • [ 932-77-4 ]
  • [ 67344-77-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4693 - 4707
  • 12
  • [ 98760-22-6 ]
  • [ 35003-56-6 ]
  • [ 67344-77-8 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 24, p. 4943 - 4946
  • 13
  • [ 67344-77-8 ]
  • [ 18759-96-1 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737
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