887581-09-1|(2-Bromo-5-methoxyphenyl)methanamine| Ambeed

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Quality Control of [ 887581-09-1 ] Purity: 97% SDS Specification

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Product Details of [ 887581-09-1 ]

CAS No. :	887581-09-1
Formula :	C₈H₁₀BrNO
M.W :	216.08
SMILES Code :	NCC1=CC(OC)=CC=C1Br
MDL No. :	MFCD07786684
InChI Key :	PWFPLVSPVFJSSZ-UHFFFAOYSA-N
Pubchem ID :	24691009

Safety of [ 887581-09-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 887581-09-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	48.31
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.25 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.1
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.44
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.76
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.95
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.87

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.36
Solubility	0.946 mg/ml ; 0.00438 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.79
Solubility	3.54 mg/ml ; 0.0164 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.43
Solubility	0.0803 mg/ml ; 0.000372 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.6 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.28

Application In Synthesis of [ 887581-09-1 ]

* 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.

Downstream synthetic route of [ 887581-09-1 ]

[ 887581-09-1 ] Synthesis Path-Downstream 1~35

1
[ 887581-09-1 ]
[ 10439-23-3 ]
4-methyl-benzenesulfinic acid 2-bromo-5-methoxy-benzylamide [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 633 - 637.
[2]Chemistry - A European Journal,2009,vol. 15,p. 10225 - 10232.

2
[ 887581-09-1 ]
[ 31562-43-3 ]
2-methyl-propane-2-sulfinic acid 2-bromo-5-methoxy-benzylamide [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 633 - 637.

3
[ 887581-09-1 ]
5-methoxy-2,3-dihydrobenzo[d]isothiazole 1-oxide [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 633 - 637.

4
[ 138642-47-4 ]
[ 887581-09-1 ]

Yield	Reaction Conditions	Operation in experiment
36%		Step A: 1-(2-Bromo-5-methoxyphenyl)methanamine 2-Bromo-5-methoxybenzonitrile (10.0 g, 47.2 mmol) was dissolved in dry tetrahydrofuran (100 mL) in a flame-dried flask and cooled in an ice bath. A solution of borane in tetrahydrofuran (75 mL, 75 mmol, 1.0 M) was added dropwise over a period of 30 minutes. The reaction mixture was stirred overnight at rt, then quenched slowly with ice water and Na2CO3 (saturated aqueous solution). After removal of THF, the residue was extracted with large amounts of EtOAc three times. The combined organic layers were washed with water, dried, and concentrated to give the crude, which was purified by silica gel column chromatography to give the desired product as a white powder (3.65 g, 36%). LCMS for C8H10BrNO (M+H)+: m/z=216.9, 219.0.
	With ammonia; hydrogen;nickel; under 25858.1 Torr;	In Scheme 75, a nitrile of formula (6) is reduced with hydrogen gas at 500 pounds-per-square-inch ("psi") pressure in the presence of a catalyst such as Raney nickel in methanol and ammonia, for example, to give the aminomethyl (7). Compound (7) may be alkylated with a compound of formula [R2-X] as described above in Scheme 74 to give compound (8). Compound (8) may be carbonylated in a manner similar to that described above for Scheme 74 to give an intermediate which cyclizes in situ to a compound (9). Compound (9) may be converted to compound (10) by demethylation with [BORONTRIBROMIDE] in dichloromethane followed by acylation of the intermediate phenol derivative with trifluoromethanesulfonic acid anhydride ("TFMSAA"). Compound (10) may be converted to compound (11) in a manner similar to that described above for Scheme 74. Alternatively, compound (11) may be converted to compound (12) by carbonylation in a manner similar to that described above for Scheme 74. Compound (12) may be converted to amide (13) in a manner similar to that described above for Scheme 74.

References: [1]Patent: US2010/190804,2010,A1 .Location in patent: Page/Page column 75-76.
[2]Patent: WO2004/14384,2004,A2 .Location in patent: Page/Page column 235-236; 239.

5
[ 887581-09-1 ]
[ 24424-99-5 ]
[ 478375-35-8 ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane; at 20℃;	Step 3: tert-butyl (2-bromo-5-methoxybenzyl)carbamate To a solution of 1-<strong>[887581-09-1](2-bromo-5-methoxyphenyl)methanamine</strong> (3.2 mmol) in DCM (15 mL) was added BOC2O (3.2 mmol). The reaction mixture was allowed to stir at rt overnight and then concentrated. The residue was purified by column chromatography to give tert-butyl (2-bromo-5-methoxybenzyl)carbamate (3.1 mmol, 95%).

References: [1]Patent: US2008/171754,2008,A1 .Location in patent: Page/Page column 105.
[2]Organic Letters,2019,vol. 21,p. 5538 - 5541.

6
[ 99848-43-8 ]
[ 887581-09-1 ]

Yield	Reaction Conditions	Operation in experiment
47%		Step 2: 1-(2-bromo-5-methoxyphenyl)methanamine Immediately prior to reaction, 2-bromo-5-methoxybenzamide (6.4 mmol) was azeotropically dried with toluene and then further dried under vacuum. This dry material was suspended in THF (15 mL) and the suspension was cooled to 0 C. To the reaction mixture was added 2M borane-dimethylsulfide complex in THF (8 mL) via syringe. The reaction mixture was heated at 70 C. and allowed to stir overnight. The mixture was cooled to 0 C. and treated with conc. HCl (0.5 mL). Vigorous gas evolution is observed, and the reaction mixture was allowed to stir at 0 C. for 15 min and then concentrated. The residue was diluted with water (10 mL) and heated at reflux for 20 min. The mixture was allowed to cool to rt and was basified with sat NaHCO3. The mixture was extracted with EtOAc. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 1-(2-bromo-5-methoxyphenyl)methanamine (3.1 mmol, 47%). LCMS: (FA) ES+216.

References: [1]Patent: US2008/171754,2008,A1 .Location in patent: Page/Page column 105.

7
[ 887581-09-1 ]
[ 98-59-9 ]
[ 1108177-18-9 ]

References: [1]Synlett,2008,p. 2851 - 2855.
[2]Synthesis,2009,p. 3127 - 3135.

8
[ 19614-12-1 ]
[ 887581-09-1 ]

References: [1]Synlett,2008,p. 2851 - 2855.
[2]Synthesis,2009,p. 3127 - 3135.
[3]ACS Combinatorial Science,2012,vol. 14,p. 211 - 217.

9
[ 887581-09-1 ]
[ 141-97-9 ]
C₁₄H₁₇NO₃ [ No CAS ]

References: [1]Organic Letters,2008,vol. 10,p. 2761 - 2763.

10
[ 887581-09-1 ]
[ 98-09-9 ]
[ 1108177-20-3 ]

References: [1]Synthesis,2009,p. 3127 - 3135.

11
[ 887581-09-1 ]
[ 920-46-7 ]
[ 1173893-64-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3193 - 3195.

12
2-bromo-5-methoxybenzyl azide [ No CAS ]
[ 887581-09-1 ]

References: [1]Chemistry - A European Journal,2009,vol. 15,p. 10225 - 10232.
[2]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 3193 - 3195.

13
[ 887581-09-1 ]
[ 5750-76-5 ]
[ 1236130-92-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	Step B: N-(2-Bromo-5-methoxybenzyl)-2,5-dichloropyrimidin-4-amine To a solution of 1-<strong>[887581-09-1](2-bromo-5-methoxyphenyl)methanamine</strong> (3.6 g, 13 mmol) and 2,4,5-trichloropyrimidine (1.60 mL, 14 mmol) in N,N-dimethylformamide (41.3 mL) was added potassium carbonate (5.53 g, 40 mmol). The resulting mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, and concentrated to give the desired product as a light yellow gel (4.65 g, 96%). LCMS for C12H10BrCl2N3O (M+H)+: m/z=361.9, 363.9.

References: [1]Patent: US2010/190804,2010,A1 .Location in patent: Page/Page column 76.

14
[ 887581-09-1 ]
[ 5813-89-8 ]
[ 1255516-34-7 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 7936 - 7938.

15
[ 887581-09-1 ]
[ 824-75-9 ]
[ 1255516-32-5 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 7936 - 7938.

16
[ 887581-09-1 ]
[ 3424-93-9 ]
[ 1255516-31-4 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 7936 - 7938.

17
[ 887581-09-1 ]
[ 98-92-0 ]
[ 1255516-33-6 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 7936 - 7938.

18
[ 887581-09-1 ]
[ 55-21-0 ]
[ 34637-66-6 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 7936 - 7938.

19
[ 887581-09-1 ]
[ 619-80-7 ]
[ 1255516-35-8 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 7936 - 7938.

20
[ 887581-09-1 ]
[ 619-55-6 ]
[ 1255516-30-3 ]

References: [1]Journal of Organic Chemistry,2010,vol. 75,p. 7936 - 7938.

21
[ 887581-09-1 ]
[ 1357295-66-9 ]
[ 1357295-74-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With acetic acid; In 1,2-dichloro-ethane; for 12h;Reflux;	General procedure: To a magnetically stirred solution of the formyl ester 8a (400 mg, 1.6 mmol) in CH2ClCH2Cl (5 mL) at room temperature, were added sequentially 2-bromobenzyl amine 3a (420 mg, 2.2 mmol) and AcOH (0.14 mL, 2.4 mmol) followed by refluxing of the mixture for 12 h. After cooling, the reaction mixture was treated with aqueous NaHCO3 solution and extracted with ethyl acetate (3 × 12 mL). The combined organic layers were washed with brine, dried (Na2SO4), and filtered. Concentration of the filtrate followed by flash chromatography (ethyl acetate/hexane, 1:6 to 2:3) furnished the cyclic enamide 9aa (480 mg, 80%) as brown viscous oil.

References: [1]Tetrahedron,2012,vol. 68,p. 1745 - 1749.

22
[ 887581-09-1 ]
[ 1357295-66-9 ]
[ 1357295-85-2 ]

References: [1]Tetrahedron,2012,vol. 68,p. 1745 - 1749.

23
[ 887581-09-1 ]
[ 1357295-64-7 ]
[ 1357295-70-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With acetic acid; In 1,2-dichloro-ethane; for 12h;Reflux;	General procedure: To a magnetically stirred solution of the formyl ester 8a (400 mg, 1.6 mmol) in CH2ClCH2Cl (5 mL) at room temperature, were added sequentially 2-bromobenzyl amine 3a (420 mg, 2.2 mmol) and AcOH (0.14 mL, 2.4 mmol) followed by refluxing of the mixture for 12 h. After cooling, the reaction mixture was treated with aqueous NaHCO3 solution and extracted with ethyl acetate (3 × 12 mL). The combined organic layers were washed with brine, dried (Na2SO4), and filtered. Concentration of the filtrate followed by flash chromatography (ethyl acetate/hexane, 1:6 to 2:3) furnished the cyclic enamide 9aa (480 mg, 80%) as brown viscous oil.

References: [1]Tetrahedron,2012,vol. 68,p. 1745 - 1749.

24
[ 887581-09-1 ]
[ 1357295-64-7 ]
[ 1357295-81-8 ]

References: [1]Tetrahedron,2012,vol. 68,p. 1745 - 1749.

25
[ 7507-86-0 ]
[ 887581-09-1 ]

Yield	Reaction Conditions	Operation in experiment
95%		To a stirred solution of bromobenzaldehyde 1b (1.0 g, 4.6 mmol) and methyl carbamate (524 mg, 7.0 mmol) in acetonitrile (12 mL), were added sequentially TFA (0.71 mL, 9.3 mmol) and tert-butyldiemthylsilane (TBDMSH) (1.53 mL, 9.3 mmol) and the resulting solution was stirred at 80 C for 6 h. The reaction mixture was concentrated in vacuo and the residue dissolved in a mixture of THF, MeOH and aq. LiOH [1.95 g, 46.5 mmol in H2O (5 mL)] (1:1:1, total 15 mL) and heated at 80 C for 16 h. The reaction mixture was cooled to RT and then treated with aqueous NaOH [700 mg in H2O (10 mL)] and the mixture was extracted with ethyl acetate (3 × 20 mL). The combined organic layers were washed with saturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent and purification of the crude material by flash chromatography (short column, ethyl acetate/hexane, 1:1 to 100% ethyl acetate, then 5:95 methanol/ethyl acetate to 10:90 methanol/ethyl acetate) furnished the benzylamine 3b (960 mg, 95%) as pale yellowish viscous liquid. 1H NMR (400 MHz, CDCl3): = 7.40 (d, J = 8.6 Hz, 1H, Ar-H), 6.93 (d, J = 3.0 Hz, 1H, Ar-H), 6.67 (dd, J = 8.6, 3.0 Hz, 1H, Ar-H), 3.86 (s, 2H, CH2NH2), 3.78 (s, 3H, OCH3), 2.12 (br. s, 2H, CH2NH2); 13C NMR (100 MHz, CDCl3): = 159.3 (C), 142.5 (C), 133.4 (CH), 114.8 (CH), 114.1 (CH), 113.7 (C), 55.4 (OCH3), 46.8 (CH2NH2); HRMS (ESI) calcd for C8H11BrNO [M+H]+ 216.0018, found 216.0017.

References: [1]Tetrahedron,2012,vol. 68,p. 1745 - 1749.

26
[ 887581-09-1 ]
[ 14401-51-5 ]
[ 1399327-66-2 ]