Home Cart 0 Sign in  
X

[ CAS No. 198967-24-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 198967-24-7
Chemical Structure| 198967-24-7
Chemical Structure| 198967-24-7
Structure of 198967-24-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 198967-24-7 ]

Related Doc. of [ 198967-24-7 ]

Alternatived Products of [ 198967-24-7 ]

Product Details of [ 198967-24-7 ]

CAS No. :198967-24-7 MDL No. :MFCD02684304
Formula : C9H10FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WWEPCBKULBKDCS-UHFFFAOYSA-N
M.W : 183.18 Pubchem ID :18357556
Synonyms :

Calculated chemistry of [ 198967-24-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.38
TPSA : 29.54 Ų

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) : -6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.05
Log Po/w (XLOGP3) : 1.53
Log Po/w (WLOGP) : 1.88
Log Po/w (MLOGP) : 2.2
Log Po/w (SILICOS-IT) : 1.23
Consensus Log Po/w : 1.78

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.08
Solubility : 1.51 mg/ml ; 0.00826 mol/l
Class : Soluble
Log S (Ali) : -1.76
Solubility : 3.19 mg/ml ; 0.0174 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.611 mg/ml ; 0.00333 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.73

Safety of [ 198967-24-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 198967-24-7 ]

* 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 [ 198967-24-7 ]
  • Downstream synthetic route of [ 198967-24-7 ]

[ 198967-24-7 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 6638-79-5 ]
  • [ 393-52-2 ]
  • [ 198967-24-7 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With triethylamine In dichloromethane at 0℃; for 0.166667 h;
Stage #2: at 0 - 20℃;
Triethylamine (5.32 mL, 37.84 mmol) was added dropwise to a solution of Ν,Ο-dimethylhydroxylamine hydrochloride (2.768 g, 28.38 mmol) in anhydrous dichloromethane (45 mL) at 0 °C. After stirring for 10 min, 2-fluorobenzoyl chloride (0.303 mL, 2.52 mmol) in anhydrous dichloromethane (15 mL) was added dropwise. The reaction mixture was returned to room temperature and stirred for 5 h. The reaction mixture was quenched with water (60 mL) and the products were extracted with dichloromethane (2 x 60 mL). The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. Purification using flash chromatography (silica gel, hexanes:ethyl acetate, gradient 93:7 to 60:40) afforded 2-Fluoro-N-methoxy-N-methyl-benzamide (3.1 16, 17 mmol) in a 90percent yield. [0
90%
Stage #1: With triethylamine In dichloromethane at 0℃; for 0.166667 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 5 h; Inert atmosphere
Triethylamine (5.32 mL, 37.8 mmol) was added dropwise to a solution of N,O-dimethylhydroxylamine hydrochloride (2.77 g, 28.4 mmol) in anhydrous dichloromethane (45 mL) at 0 °C.
After stirring for 10 min, 2-flurobenzoyl chloride (0.303 mL, 2.52 mmol) in anhydrous dichloromethane (15 mL) was added dropwise.
The reaction mixture was returned to room temperature and stirred for 5 h.
The reaction mixture was quenched with water (60 mL) and the products were extracted with dichloromethane (2 * 60 mL).
The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure.
Purification using flash chromatography (silica gel, hexanes/ethyl acetate, gradient 93:7 to 60:40) afforded 2-Fluoro-N-methoxy-N-methyl-benzamide (3.12 g, 17.0 mmol, 90percent yield).
1H NMR (500 MHz, CDCl3): δ 7.44-7.38 (2H, m), 7.19 (1H, t, J = 7.5 Hz), 7.10 (1H, t, J = 8.9 Hz), 3.55 (3H, br s), 3.35 (3H, br s).
13C NMR (125 MHz, CDCl3): δ 166.40, 158.66, (d, J = 249 Hz), 131.50, 128.90, 124.11, 123.52 (d, J = 17 Hz), 115.69 (d, J = 21 Hz), 61.21, 32.31. 19F NMR (470 MHz, CDCl3): δ -114.04 (1F, s). HRMS (ESI) calculated for C9H10FNO2H+ (M+H)+ 184.07683, found 184.07702.
62% With pyridine In tetrahydrofuran at 0 - 20℃; for 2.25 h; N,O-Dimethylhydroxylamine hydrochloride (23.4 g, 240 mmol) was suspended inTHF (100 ml) and cooled to 0 °C under nitrogen. Pyridine (32 ml, 400 mmol) was addedslowly. A solution of 2-fluorobenzoyl chloride (9.5 ml, 80 mmol) in THF (50 ml) was addedover 15 min. The reaction was removed from the ice bath and stirred at rt for 2 h. Water (100ml) and AcOEt (100 ml) were added, and the phases were separated. The aq. phase wasextracted with AcOEt (100 ml). The organic phases were pooled and washed with 1 N HCI (2x 100 ml) and 1 N NaOH (100 ml). After drying over MgSO4, the sample was concentrated toyield a yellow oil (10.7 g). The oil was purified by vacuum distillation, and a colorless oil wascollected (0.22 torr, 57-59 °C, 9.1 g, 62percent yield)2-fluoro-N-methoxy-N-methylbenzamide1H-NMR (300MHz, CDCI3) 53.34 (s, 3H), 3.54 (br, 3H), 7.10 (m, 1H), 7.19 (m, 1H),7.42 (m, 2H)
Reference: [1] RSC Advances, 2013, vol. 3, # 26, p. 10158 - 10162
[2] Patent: WO2013/142038, 2013, A2, . Location in patent: Paragraph 0130
[3] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6974 - 6992
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1415 - 1419
[5] Patent: WO2006/3096, 2006, A1, . Location in patent: Page/Page column 73
[6] Chemical Communications, 2012, vol. 48, # 71, p. 8976 - 8978
  • 2
  • [ 393-52-2 ]
  • [ 1117-97-1 ]
  • [ 198967-24-7 ]
YieldReaction ConditionsOperation in experiment
84.6% With triethylamine In dichloromethane at 0 - 20℃; To a solution of 2-fluorobenzoyl chloride (50 g, 0.31 mol) in CH2Cl2 (200 mL) was added N,O-dimethylhydroxylamine (46 g, 0.47 mol), and a solution of triethylamine (127 g, 1.26 mol) in CH2Cl2 (100 mL) at 0° C. The reaction mixture was warmed slowly to rt, and stirred for 3 h. The mixture was quenched with iced water and extracted with CH2Cl2 (200 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford 2-fluoro-N-methoxy-N-methylbenzamide (48 g, yield: 84.6percent).
Reference: [1] Patent: US2010/331320, 2010, A1, . Location in patent: Page/Page column 51; 52
  • 3
  • [ 6638-79-5 ]
  • [ 445-29-4 ]
  • [ 198967-24-7 ]
YieldReaction ConditionsOperation in experiment
73% With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; for 2 h; 2-Fluoro-N-methoxy-N-methylbenzamide was prepared in 73percent yield according to the Example 1 , Step A substituting 6-bromopicolinic acid for 2-fluorobenzoic acid.
Reference: [1] Patent: WO2015/140133, 2015, A1, . Location in patent: Page/Page column 96
Recommend Products
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 198967-24-7 ]

Fluorinated Building Blocks

Chemical Structure| 116332-54-8

[ 116332-54-8 ]

4-Fluoro-N-methoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 226260-01-1

[ 226260-01-1 ]

3-Fluoro-N-methoxy-N-methylbenzamide

Similarity: 0.91

Chemical Structure| 915087-25-1

[ 915087-25-1 ]

4-Amino-2-fluoro-N-methylbenzamide

Similarity: 0.75

Chemical Structure| 863604-64-2

[ 863604-64-2 ]

3-Fluoro-N-methoxy-N-methyl-4-nitrobenzamide

Similarity: 0.72

Chemical Structure| 445-28-3

[ 445-28-3 ]

2-Fluorobenzamide

Similarity: 0.72

Aryls

Chemical Structure| 116332-54-8

[ 116332-54-8 ]

4-Fluoro-N-methoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 226260-01-1

[ 226260-01-1 ]

3-Fluoro-N-methoxy-N-methylbenzamide

Similarity: 0.91

Chemical Structure| 122334-36-5

[ 122334-36-5 ]

N-Methoxy-N,4-dimethylbenzamide

Similarity: 0.79

Chemical Structure| 6919-61-5

[ 6919-61-5 ]

N-Methoxy-N-methylbenzamide

Similarity: 0.79

Chemical Structure| 915087-25-1

[ 915087-25-1 ]

4-Amino-2-fluoro-N-methylbenzamide

Similarity: 0.75

Amides

Chemical Structure| 116332-54-8

[ 116332-54-8 ]

4-Fluoro-N-methoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 226260-01-1

[ 226260-01-1 ]

3-Fluoro-N-methoxy-N-methylbenzamide

Similarity: 0.91

Chemical Structure| 122334-36-5

[ 122334-36-5 ]

N-Methoxy-N,4-dimethylbenzamide

Similarity: 0.79

Chemical Structure| 6919-61-5

[ 6919-61-5 ]

N-Methoxy-N-methylbenzamide

Similarity: 0.79

Chemical Structure| 915087-25-1

[ 915087-25-1 ]

4-Amino-2-fluoro-N-methylbenzamide

Similarity: 0.75

Amines

Chemical Structure| 116332-54-8

[ 116332-54-8 ]

4-Fluoro-N-methoxy-N-methylbenzamide

Similarity: 0.93

Chemical Structure| 226260-01-1

[ 226260-01-1 ]

3-Fluoro-N-methoxy-N-methylbenzamide

Similarity: 0.91

Chemical Structure| 122334-36-5

[ 122334-36-5 ]

N-Methoxy-N,4-dimethylbenzamide

Similarity: 0.79

Chemical Structure| 6919-61-5

[ 6919-61-5 ]

N-Methoxy-N-methylbenzamide

Similarity: 0.79

Chemical Structure| 915087-25-1

[ 915087-25-1 ]

4-Amino-2-fluoro-N-methylbenzamide

Similarity: 0.75