Home Cart 0 Sign in  

[ CAS No. 159503-24-9 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 159503-24-9
Chemical Structure| 159503-24-9
Structure of 159503-24-9 * Storage: {[proInfo.prStorage]}

Quality Control of [ 159503-24-9 ]

Related Doc. of [ 159503-24-9 ]

SDS
Alternatived Products of [ 159503-24-9 ]
Alternatived Products of [ 159503-24-9 ]

Product Details of [ 159503-24-9 ]

CAS No. :159503-24-9 MDL No. :MFCD03424681
Formula : C14H13NO2 Boiling Point : 411.779°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :227.26 g/mol Pubchem ID :-
Synonyms :

Safety of [ 159503-24-9 ]

Signal Word:Warning Class:
Precautionary Statements:P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 159503-24-9 ]

  • Downstream synthetic route of [ 159503-24-9 ]

[ 159503-24-9 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 591-19-5 ]
  • [ 159503-24-9 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate; lithium chloride 1.) NMP, 90 deg C; 2.) THF, MeOH, reflux, 12 h; Yield given; Multistep reaction;
  • 2
  • [ 89900-93-6 ]
  • [ 159503-24-9 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen In tetrahydrofuran
80% With palladium 10% on activated carbon; hydrogen In ethyl acetate for 24h; Synthesis of methyl 3'-amino-[1,1'-biphenyl]-4-carboxylate 11 Na2CO3 (1.1 g, 10 mmol) and palladium on charcoal (480 mg, 10% wt Pd, 0.45 mmol) were added to a solution of 3-nitrophenylboronic acid 9 (1.50 g, 9.00 mmol) and ethyl 4-bromobenzoate (2.00 g, 9.50 mmol) in EtOH (10 mL). The resultant reaction mixture was heated at reflux for 28 hours under an inert atmosphere. After cooling to room temperature, the reaction was filtered and the solvent removed in vacuo to obtain the Suzuki coupling product 10 as off-white solid. The crude product 10 obtained above was dissolved in EtOAc (10 mL) and reduced to amine in the presence of 10% Pd/C (480 mg, 10% wt Pd, 0.45 mmol) and hydrogen atmosphere for 24 hours. After complete conversion of the starting material to amine, the suspension was filtered through a celite bed. The filtrate was then diluted with water (30 mL), and extracted with EtOAc (3 x 30 mL). The combined organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The crude reaction mixture was purified by silica column chromatography (EtOAc:hexane, 1:9) to obtain the required amine 11 (1.70 g, 80% yield) as a light yellow liquid 1H NMR (600 MHz, Chloroform-d) δ 8.11 (dd, J = 8.3, 1.9 Hz, 2H), 7.65 (dd, J = 8.4, 1.9 Hz, 2H), 7.28 (d, J = 7.4 Hz, 1H), 7.04 (ddt, J = 7.6, 1.7, 0.8 Hz, 1H), 6.95 (t, J = 2.1 Hz, 1H), 6.74 (ddd, J = 7.9, 2.3, 1.0 Hz, 1H), 4.42 (q, J = 7.2 Hz, 2H), 3.80 (br, 2H), 1.44 (t, J = 7.1 Hz, 3H). 13C NMR (151 MHz, Chloroform-d) δ 166.6, 146.9, 145.8, 141.3, 129.9, 129.8, 129.2, 127.1, 117.7, 114.9, 113.8, 61.0, 14.4. IR (neat): 3252, 3219, 3004, 2823, 2661, 2547, 2091, 1674, 1608, 1589, 1519, 1488, 1415, 1391, 1336, 1319, 1285, 1295, 1257, 1219, 1186, 1154, 1129, 1048, 1017, 1001 cm-1. ESI-MS m/z 241.9 [M+H+]. HRMS calculated for (C15H16NO2)+ m/z 242.1181, Found 242.1175
With hydrogen 146 Example 146. 3 -2-S-CYCLOHEXYL-1- (3, 3-DIMETHYL-2-OXO-BUTYL)-2-OXO-1, 2-DILAYDRO-3H- 1, 3, 4-BENZOTRIAZEPIN-3-YL/-ACETYLAMINO,-BIPHENYL-4-CARBOXYLIC ACID. [0275] The title compound was obtained by the method used in the preparation of 3- {2- [5-CYCLOHEXYL-1- (3, 3-dimethyl-2-oxo-butyl) -2-oxo-1, 2-dihydro-3H-1, 3,4-benzotriazepin-3-yl]- acetylamino} -benzoic acid methyl ester (Example 1), except that 3 -AMINO-BIPHENYL-4-CARBOXYLIC acid methyl ester (prepared by catalytic hydrogenation OF 3 -NITRO-BIPHENYL-4-CARBOXYLIC acid methyl ester (Y. Matsushita, et. al., SYN. COMM., (1994), 24, 3307)) was used in place of 3- amino-benzoic acid methyl ester in step e, followed by reaction of the product obtained, in place of 3- {2- [5-cyclohexyl-1- (3, 3-dimethyl-2-oxo-butyl)-2-oxo-1, 2-dihydro-3H-1, 3,4-benzotriazepin- 3-YL]-ACETYLAMINO}-BENZOIC acid methyl ester (Example 1), according to the method of Example 2. 1H NMR (DMSO-d6) 12. 9 (1H, br s), 9.90 (1H, s), 8. 02 (2H, d), 7.88 (1H, s), 7.71 (2H, d), 7.57-7. 38 (5H, m), 7.26-7. 16 (2H, m), 4.80-4. 79 (2H, m), 4.37-4. 31 (1H, m), 4.01 (1H, m), 2. 87 (1H, m), 1.75-1. 65 (6H, m), 1.34-1. 13 (13H, m). The compound was further characterised as the N-methyl-D-glucamine salt. Found: C 61. 82, H 7.05, N 8.19% ; C35H38N4O5No.C7H17NO5No.1.7H2O requires: C 61. 51, H 7.17, N 8.54%.
In tetrahydrofuran R.9 Metyl 3'-amino-biphenyl-4-carboxylate STR15 REFERENCE EXAMPLE 9 Metyl 3'-amino-biphenyl-4-carboxylate STR15 In 100 ml of tetrahydrofuran was dissolved 2.70 g of methyl 3'-nitro-biphenyl-4-carboxylate obtained in Reference Example 8. To the solution was added 1.0 g of 10% palladium-on-carbon and the mixture was subjected to catalytic reduction for 2 hours. After removing the catalyst by filtration, the solvent was removed under reduced pressure to obtain 2.34 g of the titled compound. Melting Point 145°-148° C. 1 H-NMR(CDCl3) δ (ppm): 3.93(3H, s), 6.73(1H, m), 6.93(1H, m), 7.03-7.34(2H, m), 7.63(2H, m), 8.08(2H, m). Elementary Analysis for C14 H13 NO2 Calcd.: C,73.99; H,5.77; N,6.16. Found: C,74.04; H,5.93; N,6.19.
With palladium 10% on activated carbon; hydrogen In ethanol; water for 5h; 41 [000405] Synthesis of methyl 3’-amino-[l, 1’-biphenylj-4-carboxylate (513) [000405] Synthesis of methyl 3’-amino-[l, 1’-biphenylj-4-carboxylate (513): To a stirred solution of compound 512 (800 mg, 3.11 mmol) in EtOH (50 mL) under inert atmosphere was added 10% Pd/C (500 mg, wet) under argon atmosphere and stirred under H2 atmosphere (balloon pressure) for 5 h. After completion of the reaction, the reaction mixture was filtered through celite, washed with 50% MeOH/ CH2C12 (150 mL). The filtrate was concentrated in vacuo to obtain the crude which was purified through silicagel column chromatography in 5% MeOH/ CH2C12 to afford compound 513 (600 mg, 67%) as an off-white solid. The crude was carried for next step without further purification. TLC: 5% MeOH/ CH2C12 (R 0.4).

  • 3
  • [ 159503-24-9 ]
  • [ 174891-03-3 ]
  • 3'-[[2S-[[2-(3-chlorophenyl)-2R-hydroxyethyl]amino]propyl]amino]-[1,1'-biphenyl]-4-carboxylic acid [ No CAS ]
  • 3'-{(R)-2-[(R)-2-(3-Chloro-phenyl)-2-hydroxy-ethylamino]-propylamino}-biphenyl-4-carboxylic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3'-Amino-biphenyl-4-carboxylic acid methyl ester; 1,1-dimethylethyl ((2R)-2-(3-chlorophenyl)-2-[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)[(1R)-1-methyl-2-oxoethyl]carbamate With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane Stage #2: With hydrogenchloride In 1,4-dioxane for 1.5h; Stage #3: With lithium hydroxide In methanol Title compound not separated from byproducts;
  • 5
  • [ 13331-27-6 ]
  • [ 159503-24-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 16 percent / Pd(Ph3P)4; Na2CO3 / dioxane / 85 °C 2: 99 percent / H2 / Pd/C / tetrahydrofuran
Multi-step reaction with 2 steps 1: sodium carbonate; palladium 10% on activated carbon / ethanol / 28 h / Reflux; Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h
  • 6
  • [ 619-42-1 ]
  • [ 13331-27-6 ]
  • [ 159503-24-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; toluene / 5 h / 20 - 80 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / water; ethanol / 5 h
  • 7
  • 2,2-difluoro-7-methyl-6,7-dihydro-2H-furo[2,3-f][1,3]benzodioxole-7-carboxylic acid [ No CAS ]
  • [ 159503-24-9 ]
  • methyl 3'-[(2,2-difluoro-7-methyl-6,7-dihydro-2H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino][1,1'-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
67% With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 60℃; for 17h; 66 Example 66
methyl 3'-[(2,2-difluoro-7-methyl-6,7-dihydro-2H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino][1,1'-biphenyl]-4-carboxylate Example 66 methyl 3'-[(2,2-difluoro-7-methyl-6,7-dihydro-2H-furo[2,3-f][1,3]benzodioxole-7-carbonyl)amino][1,1'-biphenyl]-4-carboxylate The product from Example 1E (52.0 mg, 0.201 mmol), methyl 3'-amino-[1,1'-biphenyl]-4-carboxylate (CAS [159503-24-9], 82.1 mg, 0.361 mmol) and N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (57.9 mg, 0.302 mmol) were dissolved in N,N-dimethylformamide (0.5 mL) and pyridine (0.5 mL). The reaction mixture was stirred at 60° C. for 17 hours. The reaction mixture was concentrated, and the residue was purified by reverse-phase preparative HPLC on a Phenomenex Luna C8(2) 5 μm 100 Å AXIA column (30 mm*75 mm). A gradient of acetonitrile (A) and 0.1% trifluoroacetic acid in water (B) was used, at a flow rate of 50 mL/minute (0-0.5 minutes 10% A, 0.5-7.0 minutes linear gradient 10-95% A, 7.0-10.0 minutes 95% A, 10.0-12.0 minutes linear gradient 95-10% A), to yield the title compound (63.2 mg, 67%). 1H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 8.06-8.02 (m, 2H), 8.01-7.97 (m, 1H), 7.80-7.74 (m, 2H), 7.68 (dt, J=6.7, 2.2 Hz, 1H), 7.56 (s, 1H), 7.48-7.39 (m, 2H), 7.04 (s, 1H), 5.10 (d, J=9.2 Hz, 1H), 4.41 (d, J=9.2 Hz, 1H), 3.87 (s, 3H), 1.68 (s, 3H). MS (ESI+) m/z 468 (M+H)+.
  • 8
  • [ 159503-24-9 ]
  • 4-(2-methoxy-4-(1-((3'-(methylsulfonamido)-[1,1'-biphenyl]-4-carboxamido)oxy)ethyl)-5-nitrophenoxy)butanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: pyridine / dichloromethane / 12 h 2.1: sodium hydroxide / methanol; water / 3 h / Reflux 3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h 3.2: 15 h 4.1: novozyme-435 / 1,4-dioxane; aq. phosphate buffer / 120 h / 30 °C / pH 7
  • 9
  • [ 159503-24-9 ]
  • ethyl 4-(2-methoxy-4-(1-(((3’-(methylsulfonamido)-[1,1‘-biphenyl]-4-carbonyl)-12-azanyl)oxy)ethyl)-5-nitrophenoxy)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: pyridine / dichloromethane / 12 h 2.1: sodium hydroxide / methanol; water / 3 h / Reflux 3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h 3.2: 15 h
  • 10
  • [ 124-63-0 ]
  • [ 159503-24-9 ]
  • methyl 3'-(methylsulfonamido)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With pyridine In dichloromethane for 12h; Synthesis of methyl 3'-(methylsulfonamido)-[1,1'-biphenyl]-4-carboxylate 12 To a solution of amine 11 (1.00 g, 1.14 mmol) in DCM (15 mL) was added pyridine (0.70 mL, 2.21 mmol) and methane sulfonyl chloride (0.68 mL, 2.21 mmol). The reaction mixture was stirred for 12 hours and then diluted with water (30 mL) before being extracted with DCM (3 x 30 mL). The combined organic phase was washed with 1 M HCl (30 mL) and dried over Na2SO4, filtered, and concentrated in vacuo. The crude compound was purified by silica column chromatography (EtOAc:hexane, 2:8) to obtain the target sulfonamide 12 (1.2 g, 90% yield) as an off-white solid. The obtained data was comparable to the reported values.1421H NMR (400 MHz, Chloroform-d) δ 8.18 - 8.07 (m, 2H), 7.77 - 7.63 (m, 2H), 7.55 - 7.43 (m, 3H), 7.32 (ddd, J = 5.9, 3.2, 2.2 Hz, 1H), 7.06 (s, 1H), 4.43 (q, J = 7.2 Hz, 2H), 3.09 (s, 3H), 1.44 (t, J = 7.1 Hz, 3H). 13C NMR (101 MHz, Chloroform-d) δ 166.5, 144.4, 141.8, 137.5, 130.3, 130.2, 129.8, 127.1, 124.3, 120.1, 119.4, 61.2, 39.5, 14.4. IR (neat): 3247, 2971, 2937, 2876, 1788, 1697, 1606, 1585, 1519, 1508, 1467, 1411, 1367, 1323, 1277, 1218, 1210, 1187, 1151, 1135, 1109, 1080, 1053, 1013 cm-1.ESI-MS m/z 319.1
  • 11
  • [ 5798-75-4 ]
  • [ 159503-24-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium carbonate; palladium 10% on activated carbon / ethanol / 28 h / Reflux; Inert atmosphere 2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 24 h
  • 12
  • [ 159503-24-9 ]
  • 3'-methanesulfonylamino-biphenyl-4-hydroxamic acid [ No CAS ]
  • C14H14N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1.1: pyridine / dichloromethane / 12 h 2.1: sodium hydroxide / methanol; water / 3 h / Reflux 3.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h 3.2: 15 h 4.1: novozyme-435 / 1,4-dioxane; aq. phosphate buffer / 120 h / 30 °C / pH 7 5.1: water; acetonitrile / 1.5 h
  • 13
  • C13H14N2O2 [ No CAS ]
  • [ 159503-24-9 ]
  • methyl 3'-((2-cyclopentyl-1-oxoisoindolin-5-yl)diazenyl)-[1,1'-biphenyl]-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
71.5 mg With acetic acid In dichloromethane for 6.5h; Inert atmosphere; Schlenk technique;
  • 14
  • [ 499-83-2 ]
  • [ 159503-24-9 ]
  • C35H27N3O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: Pyridine-2,6-dicarboxylic acid; 3'-Amino-biphenyl-4-carboxylic acid methyl ester With pyridine at 85℃; for 0.5h; Stage #2: With triphenyl phosphite at 85℃; for 6h;
Historical Records

Related Functional Groups of
[ 159503-24-9 ]

Amines

Chemical Structure| 168619-25-8

[ 168619-25-8 ]

Methyl 3'-amino-[1,1'-biphenyl]-3-carboxylate

Similarity: 1.00

Chemical Structure| 458538-00-6

[ 458538-00-6 ]

Methyl 5-amino-[1,1'-biphenyl]-3-carboxylate

Similarity: 1.00

Chemical Structure| 811842-45-2

[ 811842-45-2 ]

Methyl 3'-amino-[1,1'-biphenyl]-4-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 343985-94-4

[ 343985-94-4 ]

Methyl 3'-amino-[1,1'-biphenyl]-3-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 400747-22-0

[ 400747-22-0 ]

Methyl 4'-amino-[1,1'-biphenyl]-3-carboxylate

Similarity: 0.97

Aryls

Chemical Structure| 168619-25-8

[ 168619-25-8 ]

Methyl 3'-amino-[1,1'-biphenyl]-3-carboxylate

Similarity: 1.00

Chemical Structure| 458538-00-6

[ 458538-00-6 ]

Methyl 5-amino-[1,1'-biphenyl]-3-carboxylate

Similarity: 1.00

Chemical Structure| 811842-45-2

[ 811842-45-2 ]

Methyl 3'-amino-[1,1'-biphenyl]-4-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 343985-94-4

[ 343985-94-4 ]

Methyl 3'-amino-[1,1'-biphenyl]-3-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 400747-22-0

[ 400747-22-0 ]

Methyl 4'-amino-[1,1'-biphenyl]-3-carboxylate

Similarity: 0.97

Esters

Chemical Structure| 168619-25-8

[ 168619-25-8 ]

Methyl 3'-amino-[1,1'-biphenyl]-3-carboxylate

Similarity: 1.00

Chemical Structure| 458538-00-6

[ 458538-00-6 ]

Methyl 5-amino-[1,1'-biphenyl]-3-carboxylate

Similarity: 1.00

Chemical Structure| 811842-45-2

[ 811842-45-2 ]

Methyl 3'-amino-[1,1'-biphenyl]-4-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 343985-94-4

[ 343985-94-4 ]

Methyl 3'-amino-[1,1'-biphenyl]-3-carboxylate hydrochloride

Similarity: 0.98

Chemical Structure| 400747-22-0

[ 400747-22-0 ]

Methyl 4'-amino-[1,1'-biphenyl]-3-carboxylate

Similarity: 0.97