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[ CAS No. 157141-27-0 ]

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2D
Chemical Structure| 157141-27-0
Chemical Structure| 157141-27-0
Structure of 157141-27-0 *Storage: {[proInfo.prStorage]}

Quality Control of [ 157141-27-0 ]

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Related Doc. of [ 157141-27-0 ]

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Product Details of [ 157141-27-0 ]

CAS No. :157141-27-0MDL No. :MFCD01321151
Formula :C14H28NPBoiling Point :339.1°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :241.35Pubchem ID :4622928
Synonyms :

Computed Properties of [ 157141-27-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 157141-27-0 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305 P351 P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 157141-27-0 ]

  • Downstream synthetic route of [ 157141-27-0 ]

[ 157141-27-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 157141-27-0 ]
  • [ 798558-55-1 ]
  • [ 798558-56-2 ]
  • 2
  • [ 82598-84-3 ]
  • [ 157141-27-0 ]
  • (E)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-2-deoxy-D-galacto-oct-2-enononitrile [ No CAS ]
  • (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-2-deoxy-D-galacto-oct-2-enononitrile [ No CAS ]
  • 3
  • [ 13096-62-3 ]
  • [ 157141-27-0 ]
  • (E)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-2-deoxy-D-gluco-oct-2-enononitrile [ No CAS ]
  • (Z)-3,7-anhydro-4,5,6,8-tetra-O-benzyl-2-deoxy-D-gluco-oct-2-enononitrile [ No CAS ]
  • 4
  • [ 6908-41-4 ]
  • 6-[1-(oxan-2-yl)-1H-pyrazol-5-yl]pyridin-3-ol [ No CAS ]
  • [ 157141-27-0 ]
  • methyl 4-[[6-[2-(2-oxanyl)-3-pyrazolyl]-3-pyridinyl]oxymethyl]benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
(1) Methyl 4-(hydroxymethyl)benzoate (37 mg) and cyanomethylenetributylphosphorane (0.12 mL) were added to a solution of the compound (50 mg) obtained in Reference Example 1-1 in toluene (1.5 mL), and the mixture was stirred under a nitrogen atmosphere at 100C for 2 hours. The reaction solution was cooled, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 2:1 to 1:2) to give methyl 4-[[6-[2-(2-oxanyl)-3-pyrazolyl]-3-pyridinyl]oxymethyl]benzoate (69 mg) as a yellow oil.
  • 5
  • ethyl 6-chloro-3-{3-[(6-fluoronaphthalen-1-yl)oxy]propyl}-7-{3-[(5-hydroxypentyl)oxy]-1,5-dimethyl-1H-pyrazol-4-yl}-1H-indole-2-carboxylate [ No CAS ]
  • [ 157141-27-0 ]
  • (rac)-ethyl 4-chloro-7-{3-[(6-fluoronaphthalen-1-yl)oxy]propyl}-2,3-dimethyl-11,12,13,14-tetrahydro-2H,10H-pyrazolo[3',4':2,3][1,6]oxazacycloundecino[4,5,6-hi]indole-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
136 mg In toluene; at 160℃; for 2h;Inert atmosphere; Microwave irradiation; In a microwave-vial ethyl 6-chloro-3-{3-[(6-fluoronaphthalen-1 -yl)oxy]propyl}-7-{3-[(5- hydroxypentyl)oxy]-1,5-dimethyl-1H-pyrazol-4-yl}-1H-indole-2-carboxylate (see Intermediate 158, 575 mg) was dissolved in 4.9 ml_ toluene and nitrogen was bubbled through. The reaction mixture was treated with [157141-27-0](tributylphosphoranylidene)acetonitrile and stirred under nitrogen atmosphere for 2h at 1600. The reaction mixture wa s concentrated under reduced pressure and purified by basic HPLC to provide the analytically pure target compound: 136 mg. LC-MS (Method 2): Rt = 1.77 min; MS (ESIpos): m/z = 605 [M+H]+ 1H-NMR (400MHz, DMSO-d6): d [ppm]= 1.26 (t, 3H), 1.31 - 1.49 (m, 4H), 1.50 - 1.65 (m, 1H), 1.86 (s, 3H), 1.89 - 2.01 (m, 1H), 2.18 (dq, 2H), 3.13 - 3.32 (m, 2H), 3.70 (s, 3H), 3.86 (t, 1H), 4.15 - 4.44 (m, 6H), 4.68 (br d, 1H), 6.82 - 6.94 (m, 1H), 7.21 (d, 1H), 7.37 (td, 1H), 7.41 - 7.48 (m, 2H), 7.66 (dd, 1H), 7.75 (d, 1H), 8.16 (dd, 1H). - contains DMF and dichloromethane.
  • 6
  • ethyl 6-chloro-7-(5-ethyl-3-{(5-hydroxypentyl)[2-(oxan-4-yl)ethyl]amino}-1-methyl-1H-pyrazol-4-yl)-3-{3-[(6-fluoronaphthalen-1-yl)oxy]propyl}-1H-indole-2-carboxylate [ No CAS ]
  • [ 157141-27-0 ]
  • (rac)-ethyl 4-chloro-3-ethyl-7-{3-[(6-fluoronaphthalen-1-yl)oxy]propyl}-2-methyl-15-[2-(oxan-4-yl)ethyl]-10,11,12,13,14,15-hexahydro-2H-pyrazolo[4',3':4,5][1,6]diazacycloundecino[3,2,1-hi]indole-8-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene; at 160℃;Inert atmosphere; Ethyl 6-chloro-7-(5-ethyl-3-{(5-hydroxypentyl)[2-(oxan-4-yl)ethyl]amino}-1 -methyl-1H-pyrazol-4- yl)-3-{3-[(6-fluoronaphthalen-1 -yl)oxy]propyl}-1H-indole-2-carboxylate (see Intermediate 154, 32 mg) was dissolved in 230 mI_ toluene, 2-[157141-27-0](tributylphosphoranylidene)acetonitrile (CAS 157141 -27, 0, 90 mI_, 340 mihoI) was added and the mixture was stirred at 1600 for 2 h under argon atmosphere. Again 2-[157141-27-0](tributylphosphoranylidene)acetonitrile (CAS 157141 -27-0, 90 mI_, 340 mihoI) was added and the mixture was stirred at 1600 over night under argon atmosphere. The reaction mixture was concentrated under reduced pressure and the crude product was purified by HPLC chromatography under basic conditions to give 12 mg of the tilte compound (93% purity) LC-MS (Method 2): Rt = 1.85 min; MS (ESIpos): m/z = 730 [M+H]+ 1H-NMR (400 MHz, DMSO-d6) d [ppm] = 0.76 - 0.95 (m, 5H), 1.04 - 1.19 (m, 4H), 1.20 - 1.45 (m, 8H), 1.61 - 1.74 (m, 1H), 1.75 - 1.92 (m, 1H), 2.1 1 - 2.23 (m, 3H), 2.24 - 2.32 (m, 1H), 2.53 - 2.70 (m, 2H), 2.74 - 2.90 (m, 2H), 2.97 (td, 1H), 3.15 - 3.32 (m, 2H), 3.45 (br d, 1H), 3.56 (br dd, 1H), 3.63 (br dd, 1H), 3.75 (s, 3H), 4.10 - 4.39 (m, 6H), 6.87 (dd, 1H), 7.23 (d, 1H), 7.32 - 7.47 (m, 3H), 7.66 (dd, 1H), 7.74 (d, 1H), 8.27 (dd, 1H).
  • 7
  • [ 1704-62-7 ]
  • 9-chloro-7-methoxy-1H,2H,3H-cyclopenta[b]quinolin-6-ol [ No CAS ]
  • [ 157141-27-0 ]
  • {2-[2-({9-chloro-7-methoxy-1H,2H,3H-cyclopentan[b]quinolin-6-yl}oxy)ethoxy]ethyl}dimethylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% A mixture of 9-chloro-7-methoxy- 1 H,2H, 3H-cyclopenta[b]quinolin-6-ol (Intermediate 11)(180.00 mg; 0.72 mmol; 1.00 eq.) and [157141-27-0](tributylphosphoranylidene)acetonitrile (695.95 mg; 2.88 mmol; 4.00 eq.) in toluene (0.9 mL) was sealed and allowed to stir at 130 C for 15 mm. To the mixture was added 2-[2-(dimethylamino)ethoxy]ethan-1-ol (384.06 mg; 2.88 mmol; 4.00 eq.) and theresulting solution was allowed to stir at 130 C hotplate for 90 mm. The mixture was cooled to rt and subjected to chromatography on silica gel using 0-100% solvent A (solvent A: 0.3% NH4OH/10% MeOH/89.7% CH2C12) in CH2C12 to provide the product as a colorless syrup (216 mg, 79%). LCMS (ES) [M+1] mlz 365.1.
  • 8
  • [(2R,3S,4R,5R,7S,9S,10S,11R,12S,13R)-12-[[(2S,5R,7R)-4-ethyl-2,5-dimethyl-1,4-oxazepan-7-yl]oxy]-2-[(1S)-2-[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyltetrahydro-2H-pyran-2-yl]oxy-1-methylethyl]-10-[(2S,3S,6R)-3-hydroxy-6-methyl-4-oxotetrahydropyran-2-yl]oxy-3,5,7,9,11,13-hexamethyl-4-(3-methylbutanoyloxy)-6,14-dioxooxacyclotetradecan-7-yl] (2S,6R)-2,6-dimethylmorpholine-4-carboxylate [ No CAS ]
  • [ 157141-27-0 ]
  • [(2R,3S,4R,5R,7S,9S,10S,11R,12S,13R)-10-[(2S,3R,4E,6R)-4-(cyanomethylene)-3-hydroxy-6-methyltetrahydropyran-2-yl]oxy-12-[[(2S,5R,7R)-4-ethyl-2,5-dimethyl-1,4-oxazepan-7-yl]oxy]-2-[(1S)-2-[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyltetrahydropyran-2-yl]oxy-1-methylethyl]-3,5,7,9,11,13-hexamethyl-4-(3-methylbutanoyloxy)-6,14-dioxooxacyclotetradec-7-yl] (2S,6R)-2,6-dimethylmorpholine-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
174 mg In tetrahydrofuran; at 80℃; for 1h; A mixture of Intermediate 5B (400.00 mg, 358.62 muetaiotaomicronIota) and 2-(tributyl-phosphanylide ne)acetonitrile (95.21 mg, 394.48 mupiiotaomicronIota) in THF (40.00 mL) was stirred at 80 C for 1 hour. The mixture was diluted with EtOAc (100 mL) and washed with water (50 mL X 3) and brine (50 mL). Then the organic phase was dried over Na2S04and concentrated under reduce pressure to give a residue. The residue was purified by column chromatography (Si02, ethyl acetate/MeOH = 1/0 to 50/1 ). 174 mg of the desired compound was obtained as yellow solid.MS Method h:Retention time Tr (min): 3.64 ; LCMS (ESI) m/z 1 138.6 [M+H]+1 H NMR spectrum (400MHz, DMSO-d6) 5.71 (br s, 1 H), 5.67 (br s, 1 H), 4.86 (br d, J=7.4 Hz, 1 H), 4.79 (br d, J=8.0 Hz, 1 H), 4.66 (br d, J=9.0 Hz, 1 H), 4.59 (br d, J=9.6 Hz, 1 H), 4.45 (br d, J=8.0 Hz, 1 H), 4.19 (br d, J=7.8 Hz, 1 H), 4.03 (br s, 1 H), 3.87 - 3.75 (m, 2H), 3.74 - 3.65 (m, 3H), 3.55 - 3.45 (m, 5H), 3.38 (s, 3H), 3.28 (br s, 1 H), 3.08 - 2.98 (m, 2H), 2.95 - 2.79 (m, 3H), 2.77 - 2.66 (m, 2H), 2.56 (br d, J=6.3 Hz, 2H), 2.43 - 2.31 (m, 3H), 2.30 - 2.08 (m, 5H), 1 .98 (br s, 3H), 1 .83 (br d, J=12.3 Hz, 2H), 1 .78 - 1 .57 (m, 6H), 1 .19 (br d, J=5.7 Hz, 3H), 1 .10 (br t, J=6.7 Hz, 6H), 1 .04 (br d, J=4.7 Hz, 18H), 0.99 - 0.83 (m, 18H), 0.78 (br d, J=6.8 Hz, 3H)
  • 9
  • (3S,4S,5R,7S,9S,10S,11R,12S,13R)-12-[(4,5-dihydroxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy]-7-hydroxy-2-{1-[(5-hydroxy-3,4-dimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy]propan-2-yl}-10-[(3-hydroxy-6-methyl-4-oxotetrahydro-2H-pyran-2-yl)oxy]-(3,5,7,9,11,13-hexamethyl-6,14-dioxooxacyclotetradecan-4-yl) 3-methylbutanoate [ No CAS ]
  • [ 157141-27-0 ]
  • C50H83NO18 [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.4 g In dichloromethane; at 20℃; for 24h; To a solution of Sequanamycine A (500 mg, 519,12 muetaiotaomicronIota) in Dichloromethane (5 ml), was added cyanomethylenetributylphophorane (286,72 muIota, 1 ,04 mmol). Then the mixture was stirred at room temperature for 24h. To the reaction mixture was added 30 ml of DCM, washed with H20 (20 ml), dried over anhydrous MgS04, filtered and the filtrate was concentrated under reduced pressure to afford 0.8 g of brown oil. The crude mixture was purified by silica gel column (DCM-lsopropanol 96/4 Rf: 0.3) to afford 0.4 g of expected product.MS Method i:Retention time Tr (min): 1 .47 ; [M+H]+ 986 ; [M-H+HCOOH]-: m/z 1030 (base peak)1 H NMR spectrum (500MHz, delta in ppm , DMSO-d6): 0.81 (d, J=6.9 Hz, 3 H), 0.95 (m, 9 H), 1 .01 (d, J=6.8 Hz, 5 H), 1 .07 (d, J=7.3 Hz, 3 H), 1 .09 (m, 6 H), 1 .13 (d, J=6.8 Hz, 3 H), 1 .17 (d, J=6.1 Hz, 3 H), 1 .22 (d, J=6.0 Hz, 3 H), 1 .24 (s, 3 H), 1 .46 ( dd, J=14.8, 10.7 Hz, 1 H), 1 .76 (m, 3 H), 1 .99 (m, 3 H), 2.08 - 2.24 (m, 5 H), 2.73 (m, 2 H), 2.80 (t, J=9.1 Hz, 1 H), 2.92 (dd, J=8.0, 2.8 Hz, 1 H), 3.03 (ddd, J=9.5, 7.1 , 2.7 Hz, 1 H), 3.19 (m, 1 H), 3.35 (m, 5 H), 3.45 (s, 3 H), 3.52 (m, 2 H), 3.59 (s, 1 H), 3.64 (m, 2 H), 3.78 (m, 3 H), 3.86 (m, 1 H), 4.10 (d, J=7.4 Hz, 1 H), 4.41 (d, J=8.8 Hz, 1 H), 4.44 (d, J=7.9 Hz, 1 H), 4.56 (s, 1 H), 4.75 (d, J=8.0 Hz, 1 H), 4.80 (d, J=8.5 Hz, 1 H), 4.85 (m, 2 H), 5.68 (t, J=1 .9 Hz, 1 H), 5.97 (d, J=5.7 Hz, 1 H)
  • 10
  • [ 15852-73-0 ]
  • 6-[1-(oxan-2-yl)-1H-pyrazol-5-yl]pyridin-3-ol [ No CAS ]
  • [ 157141-27-0 ]
  • 5-[(3-bromophenyl)methoxy]-2-[1-(oxan-2-yl)-1H-pyrazol-5-yl]pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Reference Example 6-1 5-[(3-Bromophenyl)methoxy]-2-[2-(2-oxanyl)-3 -pyrazolyl]pyridine To a solution of the compound (3.00 g) obtained in Reference Example 1-1 in toluene (31 mL), 3-bromobenzyl alcohol (2.73 g) and cyanomethylene tributylphosphorane (9.63 mL) were added, and the mixture was stirred at 100C for 1.5 hours. The reaction mixture was concentrated, and the obtained residue was purified by silica gel column chromatography (n-hexane only to ethyl acetate only) to give the title compound (4.70 g) as a brown oil. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 1.51 - 1.83 (m, 3 H) 1.97 - 2.13 (m, 2 H) 2.45 - 2.61 (m, 1 H) 3.52 - 3.68 (m, 1 H) 3.97 - 4.08 (m, 1 H) 5.13 (s, 2 H) 5.99 - 6.21 (m, 1 H) 6.50 (d, J=1.9 Hz, 1 H) 7.23 - 7.42 (m, 3 H) 7.47 - 7.52 (m, 1 H) 7.52 - 7.57 (m, 1 H) 7.59 (d, J=1.9 Hz, 1 H) 7.60 - 7.65 (m, 1 H) 8.41 - 8.46 (m, 1 H). MS ESI/APCI Multi posi: 414[M+H]+.
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