93587-23-6|7-Bromo-1H-pyrrolo[3,2-d]pyrimidin-4(5H)-one| Ambeed

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Quality Control of [ 93587-23-6 ] Purity: 95% SDS Specification

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Product Details of [ 93587-23-6 ]

CAS No. :	93587-23-6
Formula :	C₆H₄BrN₃O
M.W :	214.02
SMILES Code :	BrC1=C[NH]C2=C1NC=NC2=O
MDL No. :	MFCD09999206
InChI Key :	HNQUXIMIIVPBPC-UHFFFAOYSA-N
Pubchem ID :	135743711

Safety of [ 93587-23-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 93587-23-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	44.41
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	61.54 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.99
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	0.52
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.01
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.	0.42
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	2.39
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.07

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.1
Solubility	1.7 mg/ml ; 0.00794 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.	-1.38
Solubility	8.86 mg/ml ; 0.0414 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	-3.31
Solubility	0.106 mg/ml ; 0.000495 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.	-7.24 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)	1.95

Application In Synthesis of [ 93587-23-6 ]

* 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 [ 93587-23-6 ]

[ 93587-23-6 ] Synthesis Path-Downstream 1~20

1
[ 5655-01-6 ]
[ 93587-23-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 18.0h;	Intermediate 97 (1.70 g, 12.6 mmol) and NBS (2.69 g, 15.1 mmol) were dissolved in DMF (100 mL) and stirred for 18 h. The reaction mixture was diluted with water (50 mL) and the resulting solid was collected by filtration, dried, suspended in MeOH and filtered. The filtrate was concentrated in vacuo to give the title compound as a beige solid (2.60 g,97%). LCMS (ES+): 213.9, 215.9 (M+H)+.
	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18.0h;	Example 49: l-(4-Chloro-5H-pyrrolo[3,2-rf]pyrimidin-7-yl)-2,2,2-trifluoro-l-[l-(4- fluorophenyl)-lH-indazol-5-yl]ethanol; A mixture of 3,5-dihydropyrrolo[3,2-T\|pyrimidin-4-one (200 mg, 1.5 mmol, 1 equiv.) and N- bromosuccinimide (320 mg, 1.8 mmol, 1.2 equiv.) in 10 mL of DMF was stirred for 18 hours at room temperature. The reaction was diluted with water and resulting solid was collected by filtration, dried, suspended in MeOH, and filtered. The filtrate was concentrated in vacuo to provide 7-bromo-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one as a beige solid which was used without further purification.

References: [1]Patent: WO2011/113798,2011,A2 .Location in patent: Page/Page column 59.
[2]Patent: WO2008/70507,2008,A2 .Location in patent: Page/Page column 152-153.

2
[ 93587-23-6 ]
[ 1032650-41-1 ]

Yield	Reaction Conditions	Operation in experiment
93%		A mixture of 7-bromo-3,5-dihydropyrrolo[3,2-?]pyrimidin-4-one (100 mg, 0.5 mmol) and 6 mL of POCI3 under argon was warmed at 115C. After 3 hours, the mixture was cooled to room temperature and poured over 300 mL of ice, stirred, made basic with potassium carbonate and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 101 mg (93%) of the desired 7-bromo-4-chloro-5H-pyrrolo[3,2- djpyrimidine as beige solid which was used without further purification.
90%	With trichlorophosphate; for 2.0h;Inert atmosphere; Reflux;	Under argon atmosphere, a solution of 7-Bromo-3,5-dihydro-pyrrolo[3,2-d]pyrimidin-4-one (500 mg, 2.33 mmol) in phosphorus(V) oxychoride (6 rriL) was refluxed for 2 hours. The reaction mixture was then cooled to room temperature, concentrated and the residue was diluted with ethyl acetate. The organic layer was washed with a solution of sodium bicarbonate, brine, dried over sodium sulfate, filtered and evaporated under reduced pressure to afford compound (66a) as a pale solid (490 mg, 2.10 mmol, 90%) without further purification. lH NMR (400 MHz, DMSO-i delta 8.24 (d, J = 3.0 Hz, 1H), 8.72 (s, 1H), 12.95 (bs, 1H). MS m/z ([M+H]+) 232/234
35%	With trichlorophosphate; at 115℃; for 3.0h;	Intermediate 98 (1.30 g, 6.07 mmol) was suspended in POCI3 (60 mL) and heated at 115 C for 3 h. The reaction mixture was cooled to r.t. and poured cautiously onto ice (300 mL). The reaction mixture was basified with K2CO3 and extracted with EtOAc (3 x 200 mL). The combined organic fractions were dried (MgS04) and concentrated in vacuo to give the title compound as a beige solid (490 mg, 35%). LCMS (ES+): 231.9, 233.9, 235.9 (M+H)+.

35%

With trichlorophosphate; at 115℃; for 3.0h;

Intermediate 98 (1.30 g, 6.07 mmol) was suspended in POCl3 (60 mL) and heated at 115 C. for 3 h. The reaction mixture was cooled to r.t. and poured cautiously onto ice (300 mL). The reaction mixture was basified with K2CO3 and extracted with EtOAc (3*200 mL). The combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the title compound as a beige solid (490 mg, 35%). LCMS (ES+): 231.9, 233.9, 235.9 (M+H)+.

References: [1]Patent: WO2008/70507,2008,A2 .Location in patent: Page/Page column 153.
[2]Patent: WO2015/128334,2015,A1 .Location in patent: Page/Page column 90.
[3]Patent: WO2011/113798,2011,A2 .Location in patent: Page/Page column 59-60.
[4]Patent: US2013/102587,2013,A1 .Location in patent: Paragraph 0273; 0274.

3
3-amino-2-ethoxycarbonylpyrrole hydrochloride [ No CAS ]
[ 93587-23-6 ]

References: [1]Patent: WO2011/113798,2011,A2 .
[2]Patent: US2013/102587,2013,A1 .

4
[ 93587-23-6 ]
[ 1334713-76-6 ]

References: [1]Patent: WO2011/113798,2011,A2 .
[2]Patent: US2013/102587,2013,A1 .

5
[ 93587-23-6 ]
[ 1334713-77-7 ]

References: [1]Patent: WO2011/113798,2011,A2 .
[2]Patent: US2013/102587,2013,A1 .

6
[ 93587-23-6 ]
[ 1334712-78-5 ]

References: [1]Patent: WO2011/113798,2011,A2 .
[2]Patent: US2013/102587,2013,A1 .

7
[ 5655-01-6 ]
[ 93587-23-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 18.0h;	Intermediate 97 (1.70 g, 12.6 mmol) and NBS (2.69 g, 15.1 mmol) were dissolved in DMF (100 mL) and stirred for 18 h. The reaction mixture was diluted with water (50 mL) and the resulting solid was collected by filtration, dried, suspended in MeOH and filtered. The filtrate was concentrated in vacuo to give the title compound as a beige solid (2.60 g, 97%). LCMS (ES+): 213.9, 215.9 (M+H)+.

References: [1]Patent: US2013/102587,2013,A1 .Location in patent: Paragraph 0271; 0272.

8
[ 93587-23-6 ]
7-(1-cyclohexyl-1H-benzimidazol-5-yl)-N,N-dimethyl-4-oxo-3,4-dihydropyrrolo[3,2-d]pyrimidine-5-sulfonamide [ No CAS ]