Alternatived Products of [ 136117-93-6 ]
Product Details of [ 136117-93-6 ]
CAS No. : 136117-93-6
MDL No. : MFCD09258770
Formula :
C8 H7 BrN2
Boiling Point :
-
Linear Structure Formula : -
InChI Key : IEXMXPBKRWDOBC-UHFFFAOYSA-N
M.W :
211.06
Pubchem ID : 15098896
Synonyms :
Calculated chemistry of [ 136117-93-6 ]
Physicochemical Properties
Num. heavy atoms :
11
Num. arom. heavy atoms :
9
Fraction Csp3 :
0.12
Num. rotatable bonds :
0
Num. H-bond acceptors :
1.0
Num. H-bond donors :
0.0
Molar Refractivity :
47.86
TPSA :
17.3 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) :
-5.59 cm/s
Lipophilicity
Log Po/w (iLOGP) :
2.19
Log Po/w (XLOGP3) :
2.82
Log Po/w (WLOGP) :
2.41
Log Po/w (MLOGP) :
1.79
Log Po/w (SILICOS-IT) :
2.07
Consensus Log Po/w :
2.26
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-3.53
Solubility :
0.0622 mg/ml ; 0.000295 mol/l
Class :
Soluble
Log S (Ali) :
-2.84
Solubility :
0.305 mg/ml ; 0.00144 mol/l
Class :
Soluble
Log S (SILICOS-IT) :
-3.33
Solubility :
0.0985 mg/ml ; 0.000467 mol/l
Class :
Soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
0.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
1.65
Safety of [ 136117-93-6 ]
Application In Synthesis of [ 136117-93-6 ]
* 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 [ 136117-93-6 ]
1
[ 17282-00-7 ]
[ 2032-35-1 ]
[ 136117-93-6 ]
Yield Reaction Conditions Operation in experiment
With hydrogenchloride; sodium hydrogencarbonate 1) H2 O, a) r.t., b) 80 deg C, 2) r.t.; Yield given. Multistep reaction;
2
[ 136117-93-6 ]
[ 563-47-3 ]
[ 136117-82-3 ]
Yield Reaction Conditions Operation in experiment
Yield given. Multistep reaction;
3
[ 50-00-0 ]
[ 136117-93-6 ]
[ 217435-71-7 ]
Yield Reaction Conditions Operation in experiment
85%
With sodium acetate; acetic acid at 100℃;
80%
With sodium acetate; acetic acid at 40℃; for 24h;
Reference:
[1]Gueiffier; Mavel; Lhassani; Elhakmaoui; Snoeck; Andrei; Chavignon; Teulade; Witvrouw; Balzarini; De Clercq; Chapat
[Journal of Medicinal Chemistry, 1998, vol. 41, # 25, p. 5108 - 5112]
[2]Location in patent: scheme or table
Veron, Jean-Baptiste; Allouchi, Hassan; Enguehard-Gueiffier, Cecile; Snoeck, Robert; Andrei, Graciela; De Clercq, Erik; Gueiffier, Alain
[Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 21, p. 9536 - 9545]
4
[ 136117-93-6 ]
3-benzylsulfanylmethyl-8-bromo-6-methyl-imidazo[1,2-<i>a</i>]pyridine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 85 percent / aq. AcOH, AcONa / 100 °C
2: 92 percent / acetic acid / 2 h / 80 °C
5
[ 136117-93-6 ]
[ 136117-84-5 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
2: 80 percent / ozone, conc. HCl / H2 O; methanol / -5 - 0 °C
6
[ 136117-93-6 ]
[ 136117-88-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
2: 80 percent / ozone, conc. HCl / H2 O; methanol / -5 - 0 °C
3: 69 percent / dimethylformamide / 80 °C
7
[ 136117-93-6 ]
[ 136312-18-0 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
2: 80 percent / ozone, conc. HCl / H2 O; methanol / -5 - 0 °C
3: 69 percent / dimethylformamide / 80 °C
4: 35 percent / NaOCH3 / dimethylformamide / 80 - 90 °C
8
[ 107-20-0 ]
[ 17282-00-7 ]
[ 136117-93-6 ]
Yield Reaction Conditions Operation in experiment
85%
In ethanol for 24h; Reflux;
In acetonitrile for 4h; Heating / reflux;
151
Preparation 151; 6-methyl-8-bromoimidazo [1, 2-a] pyridine; Add chloroacetaldehyde (2.51 g, 32.08 mmol) to a solution of 2-amino-3-bromo- 5-methylpyridine (2.0 g, 10.69 mmol) in acetonitrile (200 ml). Reflux the reaction for 4 hours and then cool. Filter the reaction mixture and partition the white solid between saturated aqueous sodium bicarbonate (300 ml) and ethyl acetate. Separate the organic layer, wash with saturated aqueous sodium bicarbonate, dry over magnesium sulfate, and concentrated under reduced pressure to give the title compound as a tan solid. MS (ES) m/z = 211.0 (M++1)
Reference:
[1]Location in patent: scheme or table
Veron, Jean-Baptiste; Allouchi, Hassan; Enguehard-Gueiffier, Cecile; Snoeck, Robert; Andrei, Graciela; De Clercq, Erik; Gueiffier, Alain
[Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 21, p. 9536 - 9545]
[2]Current Patent Assignee: ELI LILLY & CO - WO2003/76442, 2003, A1
Location in patent: Page/Page column 72
9
[ 594-27-4 ]
[ 136117-93-6 ]
[ 1263061-97-7 ]
Yield Reaction Conditions Operation in experiment
at 120℃; for 0.166667h; Microwave heating at 300 watts;
152
Preparation 152; 6,8-dimethylimidazo [1, 2-a] pyridine; Microwave a mixture of 6-methyl-8-bromoimidazo [1, 2-a] pyridine (1.0 g, 4.76 mmol), tetramethyl tin (2.0 g, 11.2 mmol), and palladium tetrakis (triphenylphosphine) (0.28 g, . 024 mmol) at 120°C for 10 minutes at 300 watts. Subject the reaction mixture to flash silica gel chromatography to provide a quantitative yield of the title compound as a tan oil.
10
[ 136117-93-6 ]
C13 H18 N4
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: tris-(dibenzylideneacetone)dipalladium(0) ; ruphos; sodium t-butanolate / 1,4-dioxane / 5 h / 95 °C / Inert atmosphere
2: dichloromethane / 1 h / 20 °C
3: MP-carbonate resin / methanol / 0.5 h
Reference:
[1]Menhaji-Klotz, Elnaz; Hesp, Kevin D.; Londregan, Allyn T.; Kalgutkar, Amit S.; Piotrowski, David W.; Boehm, Markus; Song, Kun; Ryder, Tim; Beaumont, Kevin; Jones, Rhys M.; Atkinson, Karen; Brown, Janice A.; Litchfield, John; Xiao, Jun; Canterbury, Daniel P.; Burford, Kristen; Thuma, Benjamin A.; Limberakis, Chris; Jiao, Wenhua; Bagley, Scott W.; Agarwal, Saket; Crowell, Danielle; Pazdziorko, Stephen; Ward, Jessica; Price, David A.; Clerin, Valerie
[Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3685 - 3696]
11
[ 136117-93-6 ]
4-((4-(6-methylimidazo[1,2-a]pyridin-8-yl)-1,4-diazepan-1-yl)-methyl)-2-phenylthiazole
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 4 steps
1: tris-(dibenzylideneacetone)dipalladium(0) ; ruphos; sodium t-butanolate / 1,4-dioxane / 5 h / 95 °C / Inert atmosphere
2: dichloromethane / 1 h / 20 °C
3: MP-carbonate resin / methanol / 0.5 h
4: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 16 h / 50 °C
Reference:
[1]Menhaji-Klotz, Elnaz; Hesp, Kevin D.; Londregan, Allyn T.; Kalgutkar, Amit S.; Piotrowski, David W.; Boehm, Markus; Song, Kun; Ryder, Tim; Beaumont, Kevin; Jones, Rhys M.; Atkinson, Karen; Brown, Janice A.; Litchfield, John; Xiao, Jun; Canterbury, Daniel P.; Burford, Kristen; Thuma, Benjamin A.; Limberakis, Chris; Jiao, Wenhua; Bagley, Scott W.; Agarwal, Saket; Crowell, Danielle; Pazdziorko, Stephen; Ward, Jessica; Price, David A.; Clerin, Valerie
[Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3685 - 3696]
12
[ 136117-93-6 ]
C13 H18 N4 *C2 HF3 O2
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: tris-(dibenzylideneacetone)dipalladium(0) ; ruphos; sodium t-butanolate / 1,4-dioxane / 5 h / 95 °C / Inert atmosphere
2: dichloromethane / 1 h / 20 °C
Reference:
[1]Menhaji-Klotz, Elnaz; Hesp, Kevin D.; Londregan, Allyn T.; Kalgutkar, Amit S.; Piotrowski, David W.; Boehm, Markus; Song, Kun; Ryder, Tim; Beaumont, Kevin; Jones, Rhys M.; Atkinson, Karen; Brown, Janice A.; Litchfield, John; Xiao, Jun; Canterbury, Daniel P.; Burford, Kristen; Thuma, Benjamin A.; Limberakis, Chris; Jiao, Wenhua; Bagley, Scott W.; Agarwal, Saket; Crowell, Danielle; Pazdziorko, Stephen; Ward, Jessica; Price, David A.; Clerin, Valerie
[Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3685 - 3696]
13
[ 136117-93-6 ]
[ 112275-50-0 ]
C18 H26 N4 O2
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With tris-(dibenzylideneacetone)dipalladium(0) ; sodium t-butanolate; ruphos In 1,4-dioxane at 95℃; for 5h; Inert atmosphere;
Reference:
[1]Menhaji-Klotz, Elnaz; Hesp, Kevin D.; Londregan, Allyn T.; Kalgutkar, Amit S.; Piotrowski, David W.; Boehm, Markus; Song, Kun; Ryder, Tim; Beaumont, Kevin; Jones, Rhys M.; Atkinson, Karen; Brown, Janice A.; Litchfield, John; Xiao, Jun; Canterbury, Daniel P.; Burford, Kristen; Thuma, Benjamin A.; Limberakis, Chris; Jiao, Wenhua; Bagley, Scott W.; Agarwal, Saket; Crowell, Danielle; Pazdziorko, Stephen; Ward, Jessica; Price, David A.; Clerin, Valerie
[Journal of Medicinal Chemistry, 2018, vol. 61, # 8, p. 3685 - 3696]
14
3-isopropenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoquinoline
[ No CAS ]
[ 136117-93-6 ]
C20 H17 N3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
9%
With potassium phosphate; chloro(2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl)[2-(2-aminoethylphenyl)]palladium(II) methyl-t-butyl ether In tetrahydrofuran at 80℃; for 16h; Inert atmosphere;