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[ CAS No. 14097-37-1 ] {[proInfo.proName]}

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Chemical Structure| 14097-37-1
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Product Details of [ 14097-37-1 ]

CAS No. :14097-37-1 MDL No. :MFCD20690818
Formula : C10H14N2 Boiling Point : -
Linear Structure Formula :- InChI Key :PWHRVVMNFQGSJQ-UHFFFAOYSA-N
M.W : 162.23 Pubchem ID :21436741
Synonyms :

Calculated chemistry of [ 14097-37-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 55.09
TPSA : 29.26 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.5 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.79
Log Po/w (XLOGP3) : 1.11
Log Po/w (WLOGP) : 0.73
Log Po/w (MLOGP) : 1.44
Log Po/w (SILICOS-IT) : 1.58
Consensus Log Po/w : 1.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.92
Solubility : 1.97 mg/ml ; 0.0122 mol/l
Class : Very soluble
Log S (Ali) : -1.32
Solubility : 7.81 mg/ml ; 0.0481 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.58
Solubility : 0.426 mg/ml ; 0.00262 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 14097-37-1 ]

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

Application In Synthesis of [ 14097-37-1 ]

* 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 [ 14097-37-1 ]

[ 14097-37-1 ] Synthesis Path-Downstream   1~18

  • 1
  • [ 14097-37-1 ]
  • [ 52328-48-0 ]
  • N-(2-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)-4-tert-butyl-2-methoxybenzamide [ No CAS ]
  • 4
  • [ 14097-37-1 ]
  • [ 4521-61-3 ]
  • 3,4,5-trimethoxy-<i>N</i>-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 17 6-(3,4,5-Trimethoxybenzamido)-2-methyl-1,2,3,4-tetrahydroisoquinoline HCl (M-72) 6-Amino-2-methyl-1,2,3,4-tetrahydroisoquinoline was reacted with 3,4,5-trimethoxybenzoyl chloride as in Example 16 to yield 6-(3,4,5-trimethoxybenzamido)-2-methyl-1,2,3,4-tetrahydroisoquinoline. It was recovered as the HCl salt; m.p. 233.5-235 C. after purification in methanol. Anal. Calcd. for C20 H25 N2 O4 Cl:C, 61.14; H, 6.42; N, 7.13; Cl, 9.03. Found: C, 61.30; H, 6.49; N, 7.26; Cl, 9.28.
  • 5
  • [ 1231163-94-2 ]
  • [ 14097-37-1 ]
YieldReaction ConditionsOperation in experiment
69% With potassium hydroxide; In methanol; for 5h;Heating / reflux; 6-Amino-2-methyl- 1,2.3 ,4-tetrahvdroisoquinoline. A solution of 6-trifluoroacetamido-l,2,3,4-tetrahydroisoquinoline hydrochloride (280 mg, 1.0 mmol) and 37% aqueous formaldehyde (525 μl, 6.0 mmol) in methanol (5 ml) was striked at room temperature for 4 h and then treated with sodium borohydride (400 mg) and the mixture stirred at room temperature for 16 h. The solvent was removed in vacuo, the residue partitioned between water and dichloromethane, the organic layer separated and evaporated in vacuo to afford the crude N-methyl derivative. LC/MS: (PS-Bl) R4 2.56 [M+H]+ 259. Methanol (8 ml) and potassium hydroxide (224 mg, 4.0 mmol) were added and the mixture stirred and held at reflux for 5 h. The solvent was removed in vacuo, the residue partitioned between water and dichloromethane, the organic layer separated and evaporated in vacuo to afford the product as a yellow oil (112 mg, 69%). LC/MS: (PS-Bl) R12.01 [M+H]+ 163.
  • 6
  • [ 14097-37-1 ]
  • [ 647857-47-4 ]
  • [ 76-05-1 ]
  • [ 957469-32-8 ]
YieldReaction ConditionsOperation in experiment
51% EXAMPLE 6; (2R,4R)-4-methoxy-pyrrolidine-1,2-dicarboxylic acid-1-[(5-chloro-pyridin-2-yl)-amide]-2-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-amide (as the trifluoroacetate salt) (a) benzyl (2R,4R)-4-methoxy-2-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ylcarbamoyl)-pyrrolidine-1-carboxylate (as the trifluoroacetate salt)100 mg (616 μmol) 2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ylamine are dissolved in 1.5 ml DCM and at RT combined with 0.61 ml (1.22 mmol) trimethylaluminium solution (2M in toluene) and stirred for 15 min. This reaction mixture is added to 180 mg (614 μmol) 1-benzyl-2-methyl (2R,4R)-4-methoxy-pyrrolidine-1,2-dicarboxylate and rinsed with 0.5 ml DCM. The reaction mixture is stirred for three hours at RT and then added to 2N sodium hydroxide solution. The aqueous phase is extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate, filtered and evaporated to dryness i.vac. The residue is purified by RP-HPLC.Yield: 169 mg (51%)Rt value: 1.05 min (Method B)C24H29N3O4 (423.52)×CF3CO2HMass spectrum: (M+H)+=424
  • 7
  • [ 14097-37-1 ]
  • [ 957469-26-0 ]
  • [ 957469-28-2 ]
YieldReaction ConditionsOperation in experiment
54% (e) benzyl (2S,4R)-4-methoxy-2-methyl-2-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ylcarbamoyl)-pyrrolidine-1-carboxylate (as the trifluoroacetate salt); 56 mg (345 μmol) 1-benzyl (2S,4R)-4-methoxy-2-methyl-pyrrolidine-1,2-dicarboxylate are dissolved in 0.5 ml DMF and combined with 134 mg (352 μmol) HATU and with 160 μl NMM. The mixture is stirred for 15 min at RT and then combined with 100 mg (341 μmol) 2-methyl-1,2,3,4-tetrahydroisoquinolin-6-ylamine. The reaction mixture is stirred for three hours at RT and then acidified with TFA. The product is isolated from this mixture by RP-HPLC.Yield: 104 mg (54%)Rt value: 1.16 min (Method B)C25H31N3O4 (437.54)×CF3CO2HMass spectrum: (M+H)+=438
  • 8
  • [ 14097-37-1 ]
  • [ 159749-28-7 ]
  • [ 76-05-1 ]
  • [ 1080645-71-1 ]
YieldReaction ConditionsOperation in experiment
Example 1; Azetidine-1 ,2-dicarboxylic acid-1-[(4-chloro-phenyl)-amide]-2-[(2-nnethyl-1 ,2,3,4- tetrahydro-isoquinolin-6-yl)-amide] (as the trifluoroacetate salt); (a) tert. butyl 2-(2-methyl-1 ,2,3,4-tetrahydro-isoquinolin-6-ylcarbamoyl)- azetidine-1-carboxylate (as the trifluoroacetate salt); 127 mg (631 mumol) 1 -tert. butyl azetidine-1 ,2-dicarboxylate are dissolved in 4 ml THF, combined successively with 0.39 ml DIPEA (2.2 mmol) and 269 mg (0.71 mmol) HATU and stirred for one hour at RT. Then 102 mg (631 mumol) 2-methyl- 1 ,2,3,4-tetrahydro-isoquinolin-6-ylamine are added. The reaction mixture is stirred for a further hour and then evaporated to dryness i.vac. The residue is purified by RP-HPLC.Rt value: 0.42 min (Method A) Ci9H27N3O3 (345.45) x CF3CO2H Mass spectrum: (M+H)+ = 346
  • 9
  • [ 14097-37-1 ]
  • C12H15NO2 [ No CAS ]
  • [ 76-05-1 ]
  • 1-benzyl-2-methyl-azetidine-2-carboxylic acid-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-amide bis-trifluoroacetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
(b) 1 -benzyl-2-methyl-azetidine-2-carboxylic acid-(2-methyl-1 ,2,3,4- tetrahydro-isoquinolin-6-yl)-amide (as the bis-trifluoroacetate salt); 240 mg (720 μmol) methyl 1 -benzyl-2-methyl-azetidine-2-carboxylate (as the trifluoroacetate salt) are dissolved in 2 ml of methanol and combined with 4 ml (10 mmol) lithium hydroxide solution (8% in water). The reaction mixture is stirred for three hours at RT, then acidified with hydrochloric acid and freed from methanol i. vac. The aqueous phase is lyophilised. The crude product thus obtained is dissolved in 5 ml DMF and combined with 407 mg (1.1 mmol) HATU and 0.5 ml (3,3 mmol) NMM. The mixture is stirred for 15 minutes and then 174 mg (1.1 mmol) 2-methyl-1 ,2,3,4-tetrahydro-isoquinolin-6-ylamine are added. The reaction mixture is stirred for three hours at RT and then purified by RP-HPLC. <n="45"/>Rt value: 0.88 min (Method B) C22H27N3O x 2 CF3CO2H (349.48) Mass spectrum: (M+H)+ = 350
  • 10
  • [ 14097-37-1 ]
  • [ 895638-07-0 ]
  • [ 895638-08-1 ]
YieldReaction ConditionsOperation in experiment
50% With caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane; at 100℃; for 48h; Step C: 2,2,2-Trifluoro-N-[3-(3-{5-fluoro-2-[(2-methyl-1,2,3,4-tetrahydro-7-isoquinolinyl)amino]-4-pyrimidinyl}pyrazolo[1,5-a]pyridin-2-yl)phenyl]acetamide A solution N N-{3-[3-(2-chloro-5-fluoro-4-pyrimidinyl)pyrazolo[1,5-a]pyridin-2-yl]phenyl}-2,2,2-trifluoroacetamide (20 mg, 0.05 mmol), Pd2(dba)3 (8.4 mg, 0.009 mmol), xantphos (8.0 mg, 0.013 mmol), cesium carbonate (67 mg, 0.21 mmol), and 2-methyl-1,2,3,4-tetrahydro-6-isoquinolinamine (22.3 mg, 0.14 mmol) in anhydrous 1,4-dioxane, that had been previously degassed with nitrogen, was heated at 100 C. for 48 h. At this time, the crude reaction was adsorbed onto silica gel and purified by LC (DCM to 10% MeOH/DCM) to afford the product (13 mg, 50%) as a tan solid. ES-LC/MS m/z=562 [M+H]+.
  • 11
  • [ 14097-37-1 ]
  • [ 1154422-20-4 ]
YieldReaction ConditionsOperation in experiment
500 mg (3.1 mmol) 6-amino-2-methyl-1 ,2,3,4-tetrahydro-isoquinoline are dissolved in 15 ml of water and 4.3 ml (51.7 mmol) cone, hydrochloric acid, <n="38"/>cooled to 3C and combined with 272 mg (4 mmol) sodium nitrite, dissolved in 5 ml of water. The mixture is stirred for 45 minutes at 0-50C, then a solution of 262 mg (4 mmol) sodium azide in 10 ml of water is added dropwise and the mixture is stirred for one hour at the same temperature. Then the reaction mixture is diluted with 150 ml of water and made alkaline with sat. Sodium hydrogen carbonate solution. It is extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate and concentrated in vacuo.Rf value: 0.58 (silica gel; dichloromethane/ethanol/conc. ammonia 9:1 :0.1 ) Ci0Hi2N4 (188.23)Mass spectrum: (M+H)+ = 189
  • 12
  • [ 14097-37-1 ]
  • 2-methyl-azetidine-2-carboxylic acid-(2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-yl)-amide bis-trifluoroacetate [ No CAS ]
  • 13
  • [ 14097-37-1 ]
  • [ 1080645-27-7 ]
  • 14
  • [ 14097-37-1 ]
  • [ 1080645-31-3 ]
  • 15
  • [ 14097-37-1 ]
  • [ 159749-28-7 ]
  • [ 1080645-72-2 ]
  • 16
  • [ 164148-92-9 ]
  • [ 14097-37-1 ]
YieldReaction ConditionsOperation in experiment
350 mg With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 60℃; for 16h; To a stined solution of tert-butyl-6-amino-3,4-dihydroisoquinoline-2(1H)- carboxylate (500 mg, 2.01 mmol) in THF (10 mL) was added LiA1H4 (382 mg, 10.07 mmol) at 0 C. The ice bath was removed, and the reaction was stined at 60 C for 16 h. The reaction was quenched with sat. Na2SO4, and the reaction was then filtered through a celite pad. The filtrate was dried (Na2SO4), filtered and concentrated in vacuo to afford 2-methyl- 1,2,3,4-tetrahydroisoquinolin-6-amine (350 mg) as a brown semi-solid. MS (ESI) mlz 163.0 [M+H].
  • 17
  • [ 14097-37-1 ]
  • 2-chloro-4-(1-(oxetan-3-yl)-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidine [ No CAS ]
  • 2-methyl-N-(4-(1-(oxetan-3-yl)-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidin-2-yl)-1,2,3,4-tetrahydroisoquinolin-6-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
7.3 mg With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium t-butanolate; In 1,4-dioxane; at 100℃; for 4h;Inert atmosphere; A mixture containing 2-chloro-4-(1-(oxetan-3-yl)-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidine (Production Example 12, 43 mg), <strong>[14097-37-1]2-methyl-1,2,3,4-tetrahydroisoquinolin-6-amine</strong> (Synthesis literature 36, 22 mg), 4,5-bis(diphenylphosphino)-9,9-dimethyl xanthene (3.3 mg), sodium tert-butoxide (21 mg), tris(dibenzylideneacetone)dipalladium (O)(2.5 mg)and 1,4-dioxane (0.8 mL) was stirred at 100 C. for 4 hours under an argon atmosphere. The reaction mixture was concentrated under a reduced pressure, and the residue was then purified by silica gel thin layer chromatography (developing solvent: dichloromethane-methanol), and thereby 2-methyl-N-(4-(1-(oxetan-3-yl)-3-(pyridin-3-yl)-1H-pyrazol-4-yl)pyrimidin-2-yl)-1,2,3,4-tetrahydroisoquinolin-6-amine (7.3 mg) was obtained.
  • 18
  • [ 14097-37-1 ]
  • 2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-(methylsulfonyl)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]
  • 2-allyl-1-(6-(2-hydroxypropan-2-yl)pyridin-2-yl)-6-((2-methyl-1,2,3,4-tetrahydroisoquinolin-6-yl)amino)-1,2-dihydro-3H-pyrazolo[3,4-d]pyrimidin-3-one [ No CAS ]
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