[ CAS No. 21599-35-9 ] {[proInfo.proName]}

Name: 21599-35-9|2-(Methylthio)-7,8-dihydroquinazolin-5(6H)-one|98%
Brand: Ambeed
SKU: A180390
Price: 11.0 USD
Availability: InStock
Rating: 95 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 21599-35-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 21599-35-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 21599-35-9 ]

SDS Specification

Alternatived Products of [ 21599-35-9 ]

Product Details of [ 21599-35-9 ]

CAS No. :	21599-35-9	MDL No. :	MFCD13189709
Formula :	C₉H₁₀N₂OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CBDXJNWTFCTGSP-UHFFFAOYSA-N
M.W :	194.25	Pubchem ID :	13792523
Synonyms :

Calculated chemistry of [ 21599-35-9 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.44
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.61
TPSA :	68.15 Å²

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) :	-6.65 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.94
Log Po/w (XLOGP3) :	1.18
Log Po/w (WLOGP) :	1.72
Log Po/w (MLOGP) :	0.57
Log Po/w (SILICOS-IT) :	2.5
Consensus Log Po/w :	1.58

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.06
Solubility :	1.68 mg/ml ; 0.00864 mol/l
Class :	Soluble
Log S (Ali) :	-2.21
Solubility :	1.21 mg/ml ; 0.00621 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.15
Solubility :	0.137 mg/ml ; 0.000705 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Safety of [ 21599-35-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 21599-35-9 ]

* 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 [ 21599-35-9 ]
Downstream synthetic route of [ 21599-35-9 ]

[ 21599-35-9 ] Synthesis Path-Upstream 1~5

1
[ 85302-07-4 ]
[ 2986-19-8 ]
[ 21599-35-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium acetate In N,N-dimethyl-formamide at 100℃; for 5 h;	Step 2: Synthesis of 2-(methylthio)-7,8-dihydroquinazolin-5(6H)-one. To a solution of 2-((dimethylamino)methylene)cyclohexane-l,3-dione (0.5 g, 2.9 mmol) in DMF (2mL) was added sodium acetate (0.39 g, 4.7 mmol) and methyl carbamimidothioate (0.9 g, 3.5 mmol). The reaction mixture was heated at 100 ⁰C for 5 hours. On completion of the reaction, the reaction mixture was diluted with dichloromethane (30 mL). The organic layer was separated and washed with water (2 X 30 mL). The solvent was then removed under reduced pressure and the residue dissolved in EtOAc (50 mL) and washed with water (2 x 30 mL). The organic layer was dried using sodium sulfate and concentrated under reduced pressure to give the desired product (0.5 g, 86percent) as a solid. ¹H NMR (CDCl₃, 400MHz): δ 8.94 (s, IH), 3.01 (t, J = 6 Hz, 2H), 2.64 (t, J = 6.0 Hz, 2H), 2.58 (s, 3H), 2.14 (quintet, J = 6.2 Hz, 2H); LCSM [M+H]: 195.

Reference： [1] Patent: WO2010/78427, 2010, A1, . Location in patent: Page/Page column 224-225

2
[ 85302-07-4 ]
[ 14527-26-5 ]
[ 21599-35-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium carbonate In 1,4-dioxane for 8 h; Reflux	A mixture of compounds 2 (20 g, 120 mmol), sodium carbonate (15.2 g, 144 mmol) and the S-methyllisothiourea sulfate (27.11 g, 144 mmol) was added in 1,4-dioxane (450 mL). The reaction solution was refluxed for 8 h. After completion of the reaction as monitored by TLC, the mixture was cooled to room temperature. Water was added drop by drop, giving a precipitate, which was collected, and purified by flash column chromatography (petroleum ether/ethyl acetate, 8:1 v/v) to afford pure product 9. White solid. Yield: 90percent; ¹H NMR (400 MHz, DMSO) δ: 9.19 (s, 1H, -CH), 3.15 (t, J = 6.2 Hz, 2H, -CH₂), 2.92 (s, 3H, -SCH₃), 2.74 (t, J = 6.2 Hz, 2H, -CH₂), 2.17 (m, 2H, -CH₂); ¹³C NMR (100 MHz, DMSO) δ: 196.00, 175.80, 166.44, 159.63, 121.32, 55.75, 38.18, 31.91, 21.09; HRMS calculated for C₉H₁₀N₂OS 195.0592 [M+H]⁺, found 195.0581.

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 20, p. 3385 - 3390

3
[ 14527-26-5 ]
[ 21599-35-9 ]

Yield	Reaction Conditions	Operation in experiment
60.2%	for 2 h; Reflux	To a solution of 2-[(dimethylamino)methyl]-cyclohexane-1,3-dione (10.3 g, 46.0 mmol) in acetic acid (65 ml), S-methylisothiourea sulfate was added dropwise (2.44 ml, 46.0 mmol) and sodium carbonate (6.81 g, 83.4 mmol),The reaction was heated to reflux for 2 h.Add water (100 ml) and ethyl acetate (100 ml), and separate.The aqueous layer was extracted with ethyl acetate (100×2 mL).After drying over anhydrous magnesium sulfate, suction filtered, and the filtrate was evaporated.The residue is via ethanol:Water (1:1, 50ml) recrystallized,A yellow solid was obtained (6.85 g, 60.2percent).

Reference： [1] Patent: CN108484606, 2018, A, . Location in patent: Paragraph 0044; 0045; 0046

4
[ 85302-07-4 ]
[ 4338-95-8 ]
[ 27282-89-9 ]
[ 21599-35-9 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1987, # 2, p. 318 - 324

5
[ 504-02-9 ]
[ 21599-35-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 20, p. 3385 - 3390
[2] Patent: WO2010/78427, 2010, A1,

[ 21599-35-9 ] Synthesis Path-Downstream 1~17

1
[ 85302-07-4 ]
[ 4338-95-8 ]
[ 27282-89-9 ]
[ 21599-35-9 ]

Reference： [1]Bulletin de la Societe Chimique de France,1987,p. 318 - 324

2
[ 100-63-0 ]
[ 21599-35-9 ]
[ 113502-44-6 ]

Reference： [1]Bulletin de la Societe Chimique de France,1987,p. 318 - 324

3
[ 2582-30-1 ]
[ 21599-35-9 ]
[ 113502-40-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1987,p. 318 - 324

5
[ 21599-35-9 ]
thiosemicarbazone de la tetrahydro-2,5,6,7 phenyl-2 indazolone-4 [ No CAS ]

Reference： [1]Bulletin de la Societe Chimique de France,1987,p. 318 - 324

6
[ 4637-24-5 ]
[ 21599-35-9 ]
[ 1234376-89-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	In toluene; for 16.0h;Reflux;	Step 3 : Synthesis of (E)-6-((dimethylamino)methylene)-2-(methylthio)-7,8- dihydroquinazolin-5(6H)-one. To a solution of 2-(methylthio)-7,8-dihydroquinazolin-5(6H)- one (0.2 g, 1.0 mmol) in toluene (3 niL) was added DMFDMA (0.2 mL, 1.5 mmol). The reaction mixture was then refluxed for 16 hours. The reaction mixture was then cooled to room temperature and concentrated under reduced pressure. The crude compound was purified by flash column chromatography (SiO2, gradient from 100% dichloromethane to 2% methanol in dichloromethane) to give the pure desired product (0.15 g, 60%) as a solid. 1H NMR (CDCl3, 400MHz): delta 9.0 (s, IH), 7.72 (s, IH), 3.18 (s, 6H), 2.98 (t, J = 6.0 Hz, 2H), 2.92 (t, J = 6.0 Hz, 2H), 2.60 (s, 3H); LCMS [M+H]: 250

Reference： [1]Patent: WO2010/78427,2010,A1 .Location in patent: Page/Page column 224-225

7
[ 85302-07-4 ]
[ 2986-19-8 ]
[ 21599-35-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium acetate; In N,N-dimethyl-formamide; at 100℃; for 5.0h;	Step 2: Synthesis of 2-(methylthio)-7,8-dihydroquinazolin-5(6H)-one. To a solution of 2-((dimethylamino)methylene)cyclohexane-l,3-dione (0.5 g, 2.9 mmol) in DMF (2mL) was added sodium acetate (0.39 g, 4.7 mmol) and methyl carbamimidothioate (0.9 g, 3.5 mmol). The reaction mixture was heated at 100 0C for 5 hours. On completion of the reaction, the reaction mixture was diluted with dichloromethane (30 mL). The organic layer was separated and washed with water (2 X 30 mL). The solvent was then removed under reduced pressure and the residue dissolved in EtOAc (50 mL) and washed with water (2 x 30 mL). The organic layer was dried using sodium sulfate and concentrated under reduced pressure to give the desired product (0.5 g, 86%) as a solid. 1H NMR (CDCl3, 400MHz): delta 8.94 (s, IH), 3.01 (t, J = 6 Hz, 2H), 2.64 (t, J = 6.0 Hz, 2H), 2.58 (s, 3H), 2.14 (quintet, J = 6.2 Hz, 2H); LCSM [M+H]: 195.

Reference： [1]Patent: WO2010/78427,2010,A1 .Location in patent: Page/Page column 224-225

8
[ 4637-24-5 ]
[ 2002-16-6 ]
[ 21599-35-9 ]
8-(methylthio)-N-phenyl-5,6-dihydropyrimido[4,5-f]quinazolin-2-amine [ No CAS ]