1033203-41-6|6-Bromopyridine-3,4-diamine| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 1033203-41-6 ] Purity: 98% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 1033203-41-6 ]

CAS No. :	1033203-41-6
Formula :	C₅H₆BrN₃
M.W :	188.03
SMILES Code :	NC1=C(N)C=C(Br)N=C1
MDL No. :	MFCD11100655
InChI Key :	XCVAQMLOGLDTNX-UHFFFAOYSA-N
Pubchem ID :	18788657

Safety of [ 1033203-41-6 ]

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

Computational Chemistry of [ 1033203-41-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	9
Num. arom. heavy atoms	6
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	2.0
Molar Refractivity	40.75
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	64.93 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.87
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	0.51
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.02
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.	-0.03
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	0.67
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.61

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.82
Solubility	2.84 mg/ml ; 0.0151 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.44
Solubility	6.76 mg/ml ; 0.036 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	-2.16
Solubility	1.3 mg/ml ; 0.0069 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	No
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.	-7.08 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	1.0
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	1.0 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)	2.14

Application In Synthesis of [ 1033203-41-6 ]

* 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 [ 1033203-41-6 ]

[ 1033203-41-6 ] Synthesis Path-Downstream 1~30

1
[ 1033203-41-6 ]
[ 144-62-7 ]
7-bromopyrido[3,4-b]pyrazine-2,3(1H,4H)-dione hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In water; at 120℃; for 14h;	[0287] Reference V -bromo-2,3-dichloropyrido[3,4-b]pyrazine [0290] Step 1 : 7-bromopyrido[3,4-b]pyrazine-2,3(lH,4H)-dione hydrochloride [0291] To a solution of <strong>[1033203-41-6]6-bromopyridine-3,4-diamine</strong> (467 mg, 2.484 mmol) in HC1 (3726 mu, 14.90 mmol, 4 M aq) was added oxalic acid (257 mg, 2.86 mmol). The mixture was heated at 120 C for 14 h then filtered, washed with cold water and dried under vacuum to yield the title compound as a tan solid.

References: [1]Patent: WO2014/28479,2014,A1 .Location in patent: Paragraph 0287-0291; 0294-0298.

2
[ 37718-11-9 ]
[ 1033203-41-6 ]
[ 1612171-97-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With polyphosphoric acid; at 200℃; for 18h;	A mixture of <strong>[1033203-41-6]6-bromopyridine-3,4-diamine</strong> (100 mg, 0.53 mmol) and lH-pyrazole-4-carboxylic acid (60 mg, 0.53 mmol) in polyphosphoric acid (1 g) was heated in a sealed vial at 200 °C for 18 h. The reaction mixture was diluted with water and made basic by addition of NaOH (50percent aq.) and a white precipitate formed. The solid thus formed was collected by filtration and washed with water to afford the title compound (150mg, quant.). LCMS (ESI): [M+H]+ 264.1.

References: [1]Patent: WO2014/81718,2014,A1 .Location in patent: Page/Page column 67.

3
[ 1033203-41-6 ]
[ 1612171-98-8 ]

References: [1]Patent: WO2014/81718,2014,A1 .

4
[ 1033203-41-6 ]
[ 1612171-99-9 ]

References: [1]Patent: WO2014/81718,2014,A1 .

5
[ 1033203-41-6 ]
[ 1612164-32-5 ]

References: [1]Patent: WO2014/81718,2014,A1 .

6
[ 84487-15-0 ]
[ 1033203-41-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iron; acetic acid; at 75℃; for 4h;	2-Bromo-5-nitropyridin-4-amine (300.0 mg, 2.48 mmol) and Fe (300.0 mg, 5.37 mmol) were added to AcOH, and the reaction mixture was stirred at 75 C. for 4 hours and then cooled to room temperature. The reaction mixture was filtered through celite and then concentrated under reduced pressure. The residue was purified by column chromatography (n-Hex:EtOAc=50:50) on amine silica. The fractions containing the product were collected and concentrated to obtain brown solid compound of 6-bromopyridine-3,4-diamine (200.0 mg, 78%). [1234] 1H-NMR (400 MHz, DMSO-d6); delta: 7.39 (s, 1H), 6.42 (s, 1H), 5.74 (brs, 2H), 4.66 (brs, 2H)

References: [1]Patent: US2014/315888,2014,A1 .Location in patent: Paragraph 1233-1234.

7
[ 1033203-41-6 ]
[ 1429377-78-5 ]

References: [1]Patent: US2014/315888,2014,A1 .

8
[ 1033203-41-6 ]
[ 95-92-1 ]
7-bromopyrido[3,4-b]pyrazine-2,3-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	at 130℃; for 12h;	6-Bromopyridine-3,4-diamine (200.0 mg, 1.06 mmol) was added to diethyl oxalate (3.0 mL). The mixture was stirred at 130 C. for 12 hours and then cooled to room temperature. Et2O was added thereto to form a solid. The formed solid was filtered and dried under reduced pressure to obtain brown solid compound of 7-bromopyrido[3,4-b]pyrazine-2,3-diol (195.0 mg, 76%). [1236] 1H-NMR (400 MHz, DMSO-d6); delta: 12.23 (brs, 1H), 12.11 (brs, 1H), 8.09 (s, 1H), 7.05 (s, 1H)

References: [1]Patent: US2014/315888,2014,A1 .Location in patent: Paragraph 1235-1236.

9
[ 1033203-41-6 ]
3,7-dichloro-2-hydrazinylpyrido[3,4-b]pyrazine [ No CAS ]

References: [1]Patent: US2014/315888,2014,A1 .

10
[ 1033203-41-6 ]
4,8-dichloropyrido[3,4-e][1,2,4]triazolo[4,3-a]pyrazine [ No CAS ]

References: [1]Patent: US2014/315888,2014,A1 .

11
[ 1033203-41-6 ]
tert-butyl (1-(8-chloropyrido[3,4-e][1,2,4]triazolo[4,3-a]pyrazin-4-yl)azetidin-3-yl)(methyl)carbamate [ No CAS ]

References: [1]Patent: US2014/315888,2014,A1 .

12
[ 1033203-41-6 ]
1-(8-chloropyrido[3,4-e][1,2,4]triazolo[4,3-a]pyrazin-4-yl)-N-methylazetidin-3-amine [ No CAS ]

References: [1]Patent: US2014/315888,2014,A1 .

13
[ 1033203-41-6 ]
6-bromo-3-(2-trimethylsilanylethoxymethyl)-2-[1-(2-trimethylsilanylethoxymethyl)-1H-pyrazol-4-yl]-3H-imidazo[4,5-c]-pyridine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 10176 - 10191.

14
[ 37718-11-9 ]
[ 1033203-41-6 ]
6-bromo-2-(1H-pyrazol-4-yl)-3H-imidazo[4,5-c]pyridine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2014,vol. 57,p. 10176 - 10191.

15
[ 1033203-41-6 ]
6-bromo-3H-[1,2,3]triazolo[4,5-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With acetic acid; sodium nitrite; at 0 - 70℃; for 1.75h;	To a stirred solution of <strong>[1033203-41-6]6-bromopyridine-3,4-diamine</strong> 7 (2 g, 10.6 mmol) in NaNO. (2M, 25 mL) was added Acetic acid (20 mL) and stirred at 0C for 15 min and heated the contents of the reaction at 70C for 1.5 h. The reaction was cooled, poured in crushed ice the precipitated solid was filtered, dried and washed with diethyl ether to get e-bromo-SH-n^.Sltriazolo^S-clpyridine (1.0 g, 47%) as off-white solid. LC-MS (method 23): Rt = 1.26 min; m/z = 201.00 (M+H++2).

References: [1]Patent: WO2018/149986,2018,A1 .Location in patent: Page/Page column 91.

16
[ 1033203-41-6 ]
6-bromo-3-(cyclohexylmethyl)-3H-[1,2,3]triazolo[4,5-c]pyridine [ No CAS ]

References: [1]Patent: WO2018/149986,2018,A1 .

17
[ 1033203-41-6 ]
6-bromo1-(cyclohexylmethyl)-1H-[1,2,3]triazolo[4,5-c]pyridine [ No CAS ]

References: [1]Patent: WO2018/149986,2018,A1 .

18
[ 1033203-41-6 ]
6-bromo-2-(cyclohexylmethyl)-2H-[1,2,3]triazolo[4,5-c]pyridine [ No CAS ]

References: [1]Patent: WO2018/149986,2018,A1 .

19
[ 1033203-41-6 ]
6-bromo-3-(cyclohexylmethyl)-3H-imidazo[4,5-c]pyridine [ No CAS ]

References: [1]Patent: WO2018/149986,2018,A1 .

20
[ 1033203-41-6 ]
6-bromo-1-(cyclohexylmethyl)-1H-imidazo[4,5-c]pyridine [ No CAS ]

References: [1]Patent: WO2018/149986,2018,A1 .

21
[ 1033203-41-6 ]
[ 122-51-0 ]
[ 1310-73-2 ]
6-bromo-3H-imidazo[4,5-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		To a stirred solution of <strong>[1033203-41-6]6-bromopyridine-3,4-diamine</strong> (1.5 g, 8 mmol) in triethylorthoformate (7.11 g, 48 mmol) was added acetic anhydride (7.35 g, 72 mmol)) and stirred at 90C for 6h. The reaction mixture was cooled and evaporated to dryness, then 10 mL 10N NaOH solution was added and heated the contents at 60 C for 50 min. After reaction mixture was cooled acidified with AcOH to a pH 6, then added crushed ice stirred for 15 minutes precipitated solid was filtered. The precipitated solid was washed with n-pentane to get 6-bromo-3H- imidazo[4,5-c]pyridine (1.5 g, 94%) as pale brown solid. LC-MS (method 32): Rt = 0.26 min; m/z = 198.0 (M+H+).

References: [1]Patent: WO2018/149986,2018,A1 .Location in patent: Page/Page column 91.

22
[ 1033203-41-6 ]
[ 431-03-8 ]
C₉H₈BrN₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	In ethanol; for 5h;Inert atmosphere; Heating;	0.85 g (4.5 mmol) of Compound 22-1 and 0.34 g (4 mmol) of Compound 22-2 were added to 15 mL of ethanol solution in an N2 atmosphere and heated to undergo a reaction for 5 hours. After the reaction was completed, a residue obtained therefrom was separated and purified by column chromatography (petroleum ether:ethyl acetate=12:1) to obtain 0.71 g (yield: 75%) of Compound 22-3.

References: [1]Patent: US2019/218240,2019,A1 .Location in patent: Paragraph 0392; 0393.

23
[ 1033203-41-6 ]
[ 95-92-1 ]
7-bromo-1,4-dihydropyrido[3,4-b]pyrazin-2,3-dione [ No CAS ]

References: [1]Patent: WO2019/231270,2019,A1 .Location in patent: Paragraph 647-654.

24
[ 1033203-41-6 ]
[ 1558735-50-4 ]