Home Cart 0 Sign in  
X

[ CAS No. 724422-42-8 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 724422-42-8
Chemical Structure| 724422-42-8
Chemical Structure| 724422-42-8
Structure of 724422-42-8 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 724422-42-8 ]

Related Doc. of [ 724422-42-8 ]

Alternatived Products of [ 724422-42-8 ]

Product Details of [ 724422-42-8 ]

CAS No. :724422-42-8 MDL No. :MFCD21879587
Formula : C10H10BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :CXTSDEBVHHLITG-UHFFFAOYSA-N
M.W :240.10 Pubchem ID :66612874
Synonyms :

Calculated chemistry of [ 724422-42-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.3
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.81
TPSA : 20.31 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) : -6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.33
Log Po/w (XLOGP3) : 2.11
Log Po/w (WLOGP) : 1.7
Log Po/w (MLOGP) : 2.46
Log Po/w (SILICOS-IT) : 2.63
Consensus Log Po/w : 2.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.0
Solubility : 0.24 mg/ml ; 0.001 mol/l
Class : Soluble
Log S (Ali) : -2.17
Solubility : 1.63 mg/ml ; 0.0068 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.7
Solubility : 0.0481 mg/ml ; 0.0002 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 724422-42-8 ]

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 [ 724422-42-8 ]

* 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 [ 724422-42-8 ]
  • Downstream synthetic route of [ 724422-42-8 ]

[ 724422-42-8 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 147497-32-3 ]
  • [ 74-88-4 ]
  • [ 724422-42-8 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.333333 h; Inert atmosphere
Stage #2: at 0℃; for 1 h;
Synthesis of 6-bromo-2-methyl-3,4-dihydroisoquinolin-l-one (R32) R31 R32 R31 (500 mg, 2.2 mmol) in DMF (3 niL) is cooled down to 0 °C. Under argon atmosphere NaH (60percent, 121 mg, 3.0 mmol) is added and stirred for 20 min. Then methyl iodide (0.275 mL, 4.4 mmol) is added and the mixture is stirred for additional 1 h at 0 °C. Ice water is added to the reaction mixture and the precipitate is filtered by suction and dried at 50 °C in the vacuum oven for 12 h. Yield 73percent, m/z 240/242 [M+H]+, rt 0.89 min, LC-MS Method V012_S01.
73%
Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333 h; Inert atmosphere
Stage #2: at 0℃; for 1 h; Inert atmosphere
R31 (500 mg, 2.2 mmol) in DMF (3 mL) is cooled down to 0° C. Under argon atmosphere NaH (60percent, 121 mg, 3.0 mmol) is added and stirred for 20 min. Then methyl iodide (0.275 mL, 4.4 mmol) is added and the mixture is stirred for additional 1 h at 0° C. Ice water is added to the reaction mixture and the precipitate is filtered by suction and dried at 50° C. in the vacuum oven for 12 h. Yield 73percent, m/z 240/242 [M+H]+, rt 0.89 min, LC-MS Method V012_S01.
47.1% With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1 h; Compound 64.2 (0.5 g, 2.21 mmol, 1.0 eq) was dissolved in DMF (3.5 mL) and NaH (0.076 g, 3.32 mmol, 1.5 eq) was added to the reaction mixture at 0° C. Methyl iodide (0.47 g, 3.32 mmol, 1.5 eq) was added to the reaction mixture dropwise at 0° C. The reaction was stirred at 0° C. for 1 hour. After completion of the reaction, the mixture was quenched with 2N HCl solution and the product was extracted with EtOAc. Organic layers were combined, washed with brine, dried over Na2SO4 and concentrated under reduced pressure to obtain crude material. The crude was purified by column chromatography to furnish 64.3 (0.25 g, 47.1percent). MS(ES): m/z 240.10 [M+H]+.
3.3 g
Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.5 h; Inert atmosphere
Stage #2: for 2 h;
10599] To a stirred solution of 6-bromo-3,4-dihydro-2H- isoquinolin-i -one (3.5 g, 0.Oi 548 mol) in DMF (20 mE) wasadded NaR (60percent mineral oil) (i .2 g, 0.0309 mol) at 0° C. under nitrogen atmosphere and stirred for 30 mm at RT. Then methyl iodide (i .5 mE, 0.023 mol) was added and the reaction mixture was stirred for 2 h. The reaction was monitored by TEC and HNMR. Afier completion of reaction, the mixture was quenched with ice cold water (50 mE) and extracted with EtOAc (2xiOO mE). The combined organic layer was washed with water (2x50 mE) and brine (50 mE). The organic layer dried over anhydrous sodium sulfate and concentrated under reduced pressure to 6-bromo- 2-methyl-3,4-dihydroisoquinolin-i -one (3.3 gm) as an off- white solid.

Reference: [1] Patent: WO2014/140075, 2014, A1, . Location in patent: Page/Page column 209-210
[2] Patent: US2014/275025, 2014, A1, . Location in patent: Paragraph 0537; 0538
[3] Patent: US2016/251376, 2016, A1, . Location in patent: Paragraph 0852; 0855; 0856
[4] Patent: US2018/51013, 2018, A1, . Location in patent: Paragraph 0597; 0599
  • 2
  • [ 34598-49-7 ]
  • [ 724422-42-8 ]
Reference: [1] Patent: US2016/251376, 2016, A1,
[2] Patent: US2018/51013, 2018, A1,
  • 3
  • [ 1313399-72-2 ]
  • [ 724422-42-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 23, p. 9542 - 9555
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 724422-42-8 ]

Bromides

Chemical Structure| 891782-60-8

[ 891782-60-8 ]

7-Bromo-3,4-dihydro-2H-isoquinolin-1-one

Similarity: 0.95

Chemical Structure| 5543-27-1

[ 5543-27-1 ]

(4-Bromophenyl)(pyrrolidin-1-yl)methanone

Similarity: 0.92

Chemical Structure| 1254319-51-1

[ 1254319-51-1 ]

6-Bromo-2-methylisoindolin-1-one

Similarity: 0.92

Chemical Structure| 868066-91-5

[ 868066-91-5 ]

5-Bromo-2-methylisoindolin-1-one

Similarity: 0.92

Chemical Structure| 153171-22-3

[ 153171-22-3 ]

2-(4-Bromobenzyl)isoindoline-1,3-dione

Similarity: 0.90

Amides

Chemical Structure| 891782-60-8

[ 891782-60-8 ]

7-Bromo-3,4-dihydro-2H-isoquinolin-1-one

Similarity: 0.95

Chemical Structure| 5543-27-1

[ 5543-27-1 ]

(4-Bromophenyl)(pyrrolidin-1-yl)methanone

Similarity: 0.92

Chemical Structure| 1254319-51-1

[ 1254319-51-1 ]

6-Bromo-2-methylisoindolin-1-one

Similarity: 0.92

Chemical Structure| 868066-91-5

[ 868066-91-5 ]

5-Bromo-2-methylisoindolin-1-one

Similarity: 0.92

Chemical Structure| 153171-22-3

[ 153171-22-3 ]

2-(4-Bromobenzyl)isoindoline-1,3-dione

Similarity: 0.90

Related Parent Nucleus of
[ 724422-42-8 ]

Tetrahydroisoquinolines

Chemical Structure| 891782-60-8

[ 891782-60-8 ]

7-Bromo-3,4-dihydro-2H-isoquinolin-1-one

Similarity: 0.95

Chemical Structure| 1109230-25-2

[ 1109230-25-2 ]

5-Bromo-3,4-dihydroisoquinolin-1(2H)-one

Similarity: 0.89

Chemical Structure| 147497-32-3

[ 147497-32-3 ]

6-Bromo-3,4-dihydroisoquinolin-1(2H)-one

Similarity: 0.87

Chemical Structure| 943751-93-7

[ 943751-93-7 ]

7-Bromo-1,2-dihydroisoquinolin-3(4H)-one

Similarity: 0.82

Chemical Structure| 4456-77-3

[ 4456-77-3 ]

Isoquinoline-1,3(2H,4H)-dione

Similarity: 0.75