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Quality Control of [ 112253-70-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 112253-70-0 ]

SDS Specification

Alternatived Products of [ 112253-70-0 ]

Product Details of [ 112253-70-0 ]

CAS No. :	112253-70-0	MDL No. :	MFCD12674809
Formula :	C₇H₇BrN₂O	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	OFXMSVAQRRUVHA-UHFFFAOYSA-N
M.W :	215.05	Pubchem ID :	13805507
Synonyms :

Calculated chemistry of [ 112253-70-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	2.0
Molar Refractivity :	46.64
TPSA :	69.11 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.32 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.07
Log Po/w (XLOGP3) :	0.41
Log Po/w (WLOGP) :	1.14
Log Po/w (MLOGP) :	1.34
Log Po/w (SILICOS-IT) :	0.94
Consensus Log Po/w :	0.98

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.77
Solubility :	3.66 mg/ml ; 0.017 mol/l
Class :	Very soluble
Log S (Ali) :	-1.43
Solubility :	8.03 mg/ml ; 0.0373 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.49
Solubility :	0.701 mg/ml ; 0.00326 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 112253-70-0 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280	UN#:
Hazard Statements:	H302-H317	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 112253-70-0 ]

* 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.

Downstream synthetic route of [ 112253-70-0 ]

[ 112253-70-0 ] Synthesis Path-Downstream 1~23

1
[ 112253-70-0 ]
[ 95-92-1 ]
[ 113124-26-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 602 - 604

2
[ 20776-50-5 ]
[ 112253-70-0 ]

Yield	Reaction Conditions	Operation in experiment
67%		Compound 37 (9.3 g, 43.1 mmol), HOBT (13.4 g, 99 mmol) and EDC.HC1 (19 g, 99 mmol) were dissolved in DMF (40 mL). The solution was stirred at 20C for 30 minutes. To the solution, H3.H2O (20 mL). was slowly added The reaction mixture was stirred for 15 hours at room temperature. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL). The mixture was washed with saturated NaHC03 and H4CI aqueous solution. The organic layer was dried over Na2S04 and concentrated under vacuum to give the compound 38 (6.2 g, 67% yield).
53%	With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 25℃; for 18.5h;Inert atmosphere;	To a solution of 2-amino-4-bromobenzoic acid (10g, 46.3 mmol) in tetrahydrofuran (THF) (10 mL) was added HOBT (16.30 g, 106 mmol) and EDC (20.41 g, 106 mmol). The mixture was stirred at 25 C for 30 min when ammonia (30 mL, 1386 mmol) was added to the solution. The mixture was stirred at 25 C for 18 hr. The solvent was removed in vacuo when EtOAc (200 mL) was added to the mixture. The organic phase was washed with NaHC03 (aq, 100 mL X 3) and dried with NaS204. The solvent was removed to afford 2-amino-4-bromobenzamide (5.5g, 24.55 mmol, 53 % yield).
40%	With ammonium chloride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In ISOPROPYLAMIDE; at 20℃; for 24h;	To a solution of 2-amino-4-bromobenzoic acid (1 equiv) in DMA (0.23 M), were added ammonium chloride (7 equiv), HBTU (1 equiv) and diisopropylethylamine (2 equiv). The reaction mixture was stirred for 24 hours at room temperature. DMA was evaporated and the residue was purified by flash column chromatography onto silica gel eluting with a gradient of TBME/hexane to yield the desired product as a white solid. 2-Amino-4-bromo-benzamide: 40 % yield, 100 % purity) m/z (LC-MS, ESP): 215 [M+H]+ R/T = 3.00 min

Example 5.25a. Synthesis of 2-amino-4-bromobenzamideA solution of 2-amino-4-bromobenzoic acid (1 g, 4.63 mmol), NH4C1 (1.8g, 32.41 mmol), TBTU (1.5 g, 4.63 mmol) and diisopropylethylamine (1.2 g, 9.26 mmol) in DMF (30 mL) was stirred at room temperature overnight. Then the mixture was adjusted to pH 8.0 with saturated Na2C03 and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over Na2S04 and concentrated to give the desired yellow product. MS (ESI): 215, 217 (MH+).

Reference： [1]Patent: WO2012/13643,2012,A1 .Location in patent: Page/Page column 48
[2]Patent: WO2017/98440,2017,A1 .Location in patent: Page/Page column 120
[3]Patent: WO2008/23161,2008,A1 .Location in patent: Page/Page column 119
[4]Patent: WO2011/75699,2011,A2 .Location in patent: Page/Page column 206
[5]Journal of Agricultural and Food Chemistry,2015,vol. 63,p. 6883 - 6889
[6]Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 195,p. 194 - 200

3
[ 112253-70-0 ]
[ 122-51-0 ]
[ 194851-16-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With trifluoroacetic acid; In ISOPROPYLAMIDE; at 160℃; for 0.5h;Microwave radiation;	To a solution of <strong>[112253-70-0]2-amino-4-bromo-benzamide</strong> (1 equiv) in DMA (0.14 M) were added triethyl orthoformate (10 equiv) and trifluoroacetic acid (1 equiv). The reaction vessel was sealed and exposed to microwave radiation (160 0C, medium absorption setting) for 30 minutes. The reaction mixture was concentrated in vacuo and the residue was filtered through a silica pad with 10 % methanol in ethyl acetate yielding the required product as a pale yellow solid. <n="121"/>7-Bromo-3H-quinazolin-4-one: (71 % yield, 100 % purity) m/z (LC-MS, ESP): 268 [M+H]+ R/T = 2.94 min

Reference： [1]Patent: WO2008/23161,2008,A1 .Location in patent: Page/Page column 119-120

4
[ 112253-70-0 ]
[ 113124-31-5 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 602 - 604

5
[ 112253-70-0 ]
[ 113124-35-9 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1987,vol. 26,p. 602 - 604

6
[ 112253-70-0 ]
[ 74974-54-2 ]
[ 573681-17-1 ]

Yield	Reaction Conditions	Operation in experiment
	for 0.5h;Heating / reflux;	Reflux a solution of <strong>[112253-70-0]2-amino-4-bromobenzamide</strong> (27 g, 0.13 mol; see Joshi and Chaudhari (1987) Indian J. CHEM., Sect. B, 26B (6) : 602-4) in 2-CHLORO-1, 1, 1-TRIMETHOXYETHANE (50 mL) for 30 minutes, during which time a large precipitate appears. Evaporate the mixture fully and triturate with ether to collect 7-BROMO-2-CHLOROMETHYL-3H-QUINAZOLIN-4-ONE as a white solid

Reference： [1]Patent: WO2004/55003,2004,A1 .Location in patent: Page 121

7
[ 112253-70-0 ]
[ 109-94-4 ]
[ 194851-16-6 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium methylate; In ethanol; for 1.5h;Heating / reflux;	2) 4-Bromoanthranilic amide (40 g, 186 mmol) obtained in 1) was dissolved in ethanol (400 mL). Thereto was added sodium methoxide (54.2 g, 93 mmol) with stirring under ice-cooling and then ethyl formate (60.1 mL, 744 mmol) was added dropwise. The mixture was heated under reflux for 1.5 hrs. The reaction mixture was allowed to cool to room temperature and water (500 mL) was added and then acetic acid (40 mL) was added. The mixture was concentrated under reduced pressure and water (200 mL) was added. The precipitate was collected by filtration and dried to give 7-bromo-3H-quinazolin-4-one (35 g, 156 mmol, 84%). 7-bromo-3H-quinazolin-4-one [0153] 1H NMR (DMSO-d6) delta ppm: 7.68 (dd, J=1.7, 8.5 Hz, 1H), 7.88 (d, J=1.7 Hz, 1H), 8.03 (d, J=8.5 Hz, 1H), 8.14 (s, 1H).

Reference： [1]Patent: US2004/116422,2004,A1 .Location in patent: Page/Page column 32

8
[ 79603-03-5 ]
[ 112253-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;platinum(IV) oxide; In ethyl acetate; for 41.5h;	1) To a solution of 2,5-dibromonitrobenzene (80 g, 285 mmol) in DMF (500 mL) was added copper cyanide (I) (38 g, 427 mmol) and the mixture was stirred at 100 C. for 1.5 hrs. The reaction mixture was allowed to reach room temperature and toluene (750 mL)-water (1250 mL) was added. Then, Celite (50 g) was added, and after thorough stirring, insoluble material was filtered off. The filtrate was partitioned and the organic layer was washed successively with water (500 mL), 1% aqueous ammonia (250 mL×2), water (250 mL) and saturated brine (500 mL), and dried over anhydrous sodium sulfate, after which the solvent was evaporated under reduced pressure to give a yellow solid (61.4 g) containing 2-cyano-5-bromonitrobenzene as a main component. This was dissolved in ethyl acetate (270 mL) and platinum oxide monohydrate (330 mg, 1.35 mmol) was added. The inside of the reaction container was displaced with hydrogen and the mixture was stirred under a hydrogen atmosphere for 41.5 hrs. Insoluble material was filtered off and the residue was washed with ethyl acetate (200 mL) and then with ethanol (100 mL). The filtrate was evaporated under reduced pressure, and after drying, suspended in ether (250 mL). The suspension was stirred with heating under reflux. The mixture was allowed to cool to room temperature and the insoluble material was collected by filtration to give 4-bromoanthranilic amide (40 g, 186 mmol, 65%). [CHEMMOL-00365] 2-cyano-5-bromonitrobenzene [0150] 1H NMR (DMSO-d6) delta ppm: 8.10 (d, J=8.3 Hz, 1H), 8.21 (dd, J=1.8, 8.3 Hz, 1H), 8.57 (d, J=1.8 Hz, 1H) [CHEMMOL-00366] 4-bromoanthranilic amide [0151] 1H NMR (DMSO-d6) delta ppm: 6.61 (dd, J=1.8, 8.4 Hz, 1H), 6.81 (br s, 2H), 6.89 (d, J=1.8 Hz), 7.17 (br s, 1H), 7.46 (d, J=8.4 Hz, 1H), 7.79 (br s, 1H)

Reference： [1]Patent: US2004/116422,2004,A1 .Location in patent: Page/Page column 31-32

9
[ 304858-65-9 ]
[ 112253-70-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; acetic acid; for 4h;	2-Amino-4-bromobenzonitrile was dissolved in 4: 1 AcOHZH2SO4 to form a suspension. The mixture was stirred for 4 h until it became clear and all starting material was consumed as monitored by LC-MS. The solution was poured into ice water and extracted by EtOAc three times. The combined organic layer was washed with brine and dried over Na2SO4. After filtration, the solvent was removed to provide 11-1. Substituted benzyloxy acetic acid (1.1 equiv) was treated with 2 M oxalyl chloride in DCM for 3 h and concentrated to give the corresponding acid chloride, which was then added to a stirred solution of 11-1 and pyridine (5 equiv) in DCM. The reaction mixture was stirred for 3 h until 11-1 was consumed as monitored by LC-MS. The precipitate was collected by filtration and was dried under vacuum to provide 11-2 as white solid. 11-2, potassium carbonate (4 equiv), boronic ester (1.5 equiv) and Pd(PPh3 )4( 10%) were dissolved in 4: 1 dioxane/water and sealed in a microwave tube. The reaction mixture was degassed and heated by microwave for 30min at 140 0C. The solvent was removed and the residue was subjected to preparative HPLC to provide product 11-3 as a TFA salt.

Reference： [1]Journal of Chemical Research,2011,vol. 35,p. 480 - 483
[2]Patent: WO2010/56758,2010,A1 .Location in patent: Page/Page column 118

10
[ 106967-74-2 ]
[ 112253-70-0 ]
C₁₆H₁₅BrN₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In dichloromethane; for 3h;	2-Amino-4-bromobenzonitrile was dissolved in 4: 1 AcOHZH2SO4 to form a suspension. The mixture was stirred for 4 h until it became clear and all starting material was consumed as monitored by LC-MS. The solution was poured into ice water and extracted by EtOAc three times. The combined organic layer was washed with brine and dried over Na2SO4. After filtration, the solvent was removed to provide 11-1. Substituted benzyloxy acetic acid (1.1 equiv) was treated with 2 M oxalyl chloride in DCM for 3 h and concentrated to give the corresponding acid chloride, which was then added to a stirred solution of 11-1 and pyridine (5 equiv) in DCM. The reaction mixture was stirred for 3 h until 11-1 was consumed as monitored by LC-MS. The precipitate was collected by filtration and was dried under vacuum to provide 11-2 as white solid. 11-2, potassium carbonate (4 equiv), boronic ester (1.5 equiv) and Pd(PPh3 )4( 10%) were dissolved in 4: 1 dioxane/water and sealed in a microwave tube. The reaction mixture was degassed and heated by microwave for 30min at 140 0C. The solvent was removed and the residue was subjected to preparative HPLC to provide product 11-3 as a TFA salt.

Reference： [1]Patent: WO2010/56758,2010,A1 .Location in patent: Page/Page column 118

11
[ 100-52-7 ]
[ 112253-70-0 ]
[ 1152237-10-9 ]

Yield	Reaction Conditions	Operation in experiment
69%	With sodium metabisulfite; In ISOPROPYLAMIDE; for 3h;Reflux;	Synthesis of 4:A mixture of 3 (1.5 g, 7.2 mmol) with benzaldehyde (0.73 mL, 7.2 mmol) and sodium bisulfite (1.1 g, 10.8 mmol) in dimethylacetamide (DMA) (5 mL) was heated at reflux for 3 h. After pouring into H2O (20 mL), the solution was allowed to warm up to room temperature. The solid which formed was filtered, washed with H2O, followed by Et2O to provide 4 (1.5 g, 69%) as a yellow solid, after recrystallization with MeOH/EtOAc.

Reference： [1]Patent: US2010/160314,2010,A1 .Location in patent: Page/Page column 69

12
[ 1152237-09-6 ]
[ 112253-70-0 ]

Yield	Reaction Conditions	Operation in experiment
67%		Synthesis of 3:A mixture of 2 (2.0 g, 10.6 mmol) in EtOAc (200 mL) was treated with SnCl2 (9.4 g, 42 mmol) at reflux for 20 min. After addition of 1N NaOH, the formed solid was filtered and washed with EtOAc. The organic phase was separated. The aqueous phase was neutralized (pH7) and extracted with EtOAc (2×70 mL). The combined organic extracts were concentrated to provide 3 (1.53 g, 67%) as a tan solid.

Reference： [1]Patent: US2010/160314,2010,A1 .Location in patent: Page/Page column 69

13
[ 112253-70-0 ]
(9H-fluoren-9-yl)methyl 2-(7-bromo-4-oxo-3,4-dihydroquinazolin-2-yl)pyrrolidine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2011/75699,2011,A2

14
[ 112253-70-0 ]
7-bromo-2-(pyrrolidin-2-yl)quinazolin-4(3H)-one [ No CAS ]

Reference： [1]Patent: WO2011/75699,2011,A2

15
[ 112253-70-0 ]
11-bromo-2,3,5,6-tetrahydro-1H-pyrrolo[2',1':3,4]pyrazino[2,1-b]quinazolin-8(13bH)-one [ No CAS ]

Reference： [1]Patent: WO2011/75699,2011,A2

16
[ 112253-70-0 ]
[ 103321-52-4 ]
(9H-fluoren-9-yl)methyl 2-(5-bromo-2-carbamoylphenylcarbamoyl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃;	Example 5.25c. Synthesis of (9H-fluoren-9-yl)methyl 2-(5-bromo-2- carbamoylphenylcarbamovDpyrrolidine- 1 -carboxylateA solution of (9H-fluoren-9-yl)methyl 2-(chlorocarbonyl)pyrrolidine- l-carboxylate (600 mg, 1.8 mmol), <strong>[112253-70-0]2-amino-4-bromobenzamide</strong> (400 mg, 1.8 mmol), and Et3N (2 mL) in THF was stirred at room temperature . The reaction was monitored by TLC. After diluting with H20 (50 mL), the mixture was extracted with ethyl acetate (3 x 100 mL). The organic layers were dried over Na2S04 and concentrated to give yellow residue, which was purified by column chromatography. MS (ESI): 534, 536(MH+)

Reference： [1]Patent: WO2011/75699,2011,A2 .Location in patent: Page/Page column 207

17
[ 3282-30-2 ]
[ 112253-70-0 ]
[ 1354455-85-8 ]

Yield	Reaction Conditions	Operation in experiment
		Example 1N-{4-[2-tert-Butyl-4-(6-methyl-2-oxo-1,2-dihydro-pyridin-3-yl)-quinazolin-7-yl]-phenyl}-methanesulfonamide (I-1; SCHEME A); step 1: To a suspension of 20a (3 g, 14 mmol, CASRN 112253-70-0) in DCM cooled to 0 C. and maintained under a N2 atmosphere was added TEA and the suspension stirred for 15 min. To the suspension was added slowly pivaloyl chloride (1.68 g, 14 mmol) the solution was stirred over night RT. The solution was recooled to 0 C. and a second aliquot of pivaloyl chloride (300 muL) was added and the resulting mixture stirred for 2 h at 0 C. for 2 h then at RT for 2 h. The reaction mixture was concentrated in vacuo to afford 20b which was used without additional purification.step 2: To a suspension of 20b (4.2 g, 14 mmol) and EtOH (28 mL) was added aqueous NaOH (2.8 mL, 28 mmol, 10M solution) and the resulting mixture was heated at reflux under an N2 atmosphere for 1.5 h. The solution was cooled to RT, poured over ice and neutralized with1N HCl. The resulting mixture was twice extracted with EtOAc. The combined extracts were washed with brine, dried (MgSO4), filtered and evaporated to afford 2.07 g of 22a as a yellow solid.step 3: A microwave vial was charged with 22a (0.5 g, 1.78 mmol), 4-methansulfonamido-phenyl boronic acid (0.421 g, 1.96 mmol, CASRN 380430-57-9), Pd(PPh3)4 (0.206 g, 0.178 mmol), Na2CO3 (0.566 g, 5.34 mmol), MeOH (3 mL) and toluene (1.5 mL). The vial was flushed with Ar for 5 min, sealed and irradiated in a microwave synthesizer at 115 C. The reaction mixture was cooled and concentrated. The insoluble material was triturated with Et2O which afford 0.55 g (84.3%) of 22b as a brown solid.step 4: To a suspension of 22b (0.1 g, 0.27 mmol) in benzene (0.5 mL) was added sequentially diethylaniline (73.0 muL, 0.45 mmol) and POCl3 (14.8 muL). The mixture was heated at reflux for 6 h, cooled and diluted with EtOAc. The resulting solution was washed sequentially with 1 N HCl, H2O, satd. aq. NaHCO3, H2O and brine. The solution was dried (MgSO4), filtered and evaporated to afford 24.step 5: A vial was charged with 24 (0.107 g, 0.274 mmol), 6-methyl-2-methoxy-pyridin-3-yl boronic acid (0.055 g, 0.33 mmol), PdC12(dPPf).CH2Cl2 (0.010 g, 0.014 mmol), Cs2CO3 (0.822 g, 0.268 mmol). dioxane (1 mL) and H2O (0.25 mL), purged with Ar for 10 min sealed and heated for 1 h. The solution was cooled to RT, diluted with EtOAc and sequentially extracted with twice with H2O and brine. The resulting solution was dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (10 to 30% EtOAc) to afford 0.08 g of 26.step 6: A mixture of 26 (0.08 g, 0.169 mmol), 48% aq. HBr (52 muL) and HOAc was heated in sealed tube at 60 C. for 3 h. The tube was cooled and the mixture diluted with EtOAc, neutralized with satd. aq. NaHCO3 and stirred overnight at RT. The EtOAc had evaporated and the remaining yellow solid was filtered and washed with EtOAc and H2O. The solid was dried at 70 C. overnight in a vacuum oven which afforded I-1.

Reference： [1]Patent: US2012/9144,2012,A1 .Location in patent: Page/Page column 15

18
[ 112253-70-0 ]
[ 1354455-86-9 ]