Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 912846-68-5 | MDL No. : | MFCD18157611 |
Formula : | C14H19FN2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SKNYBTIRSWCZMQ-UHFFFAOYSA-N |
M.W : | 266.31 | Pubchem ID : | 57659685 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With palladium 10% on activated carbon; hydrogen; In methanol; under 3102.97 Torr; for 3.0h; | To a solution of erl-butyl 7-fl uoro-6-nitro-3 ,4-dihydroisoquinoline-2( 1 H)carboxylate (161a) (0.5 g, 1.688 mmol) (Prepared as described in the literature (a) Harling, J.D; Watson, N. S.; Young, R. J. WO 2006/108709 Al Oct 19, 2006; (b) Watson, N. S.; Adams, C.: Belton, D.; Brown, D.; Bums-Kurtis, C. L.; Chaudry, L.; Chan, C.; Convery,Maire A.; Davies, D. E.; Exail, A. M. et al, i?ioorganic & Mc?dicinaI (?hc?rnisirv Letters (201 1), 21(6), 1588-1592) in methanol (20 mL) was added palladium on carbon (10%) (0.359 g, 3.38 rnmol) and hydrogenated for 3 h at 60 psi. The catalyst was removed by filtration through Celite and the filtrate was concentrated in vacuum. The residue was purified by flash column chromatography [silica gel 12 g, eluting with ethyl acetate inhexanes from 0-100%] to furnish ieri-butyl 6-am ino-7-fluoro-3 ,4-dihydroisoqu I noline2(1 H)-carboxylate (161b)(0.256 g, 57% yield) as a white solid; ?H NMR (300 MHz, DMSO-d?,) 66.81 (d,.J 12.0Hz, IN), 6.51 (d,J=9.l Hz, IH), 4.98(s, 2H, D20 exchangeable), 4.31 (s, 21-1), 3.47 (t,.I5.9 Hz, 2H), 2.59 O .J 5.9 Hz, 2H), 1.41 (s, 9H); 19F NMR (282 MHz, DMSO-cIc) 6 -137.71; MS (ES): MS (ES±) 289.2 (M+Na), 555.4 (2M+Na), MS (ES-) 265.1 (M-1); Analysis calculated for C14H,9FN202: C, 63.14; H, 7.19;N, 10.52; Found: C, 63.41; H, 7.27; N, 10.43. |
With hydrogen;palladium 10% on activated carbon; In ethanol; under 760.051 Torr; for 3.0h; | Intermediate 40 1 ,1-Dimethylethyl 6-amino-7-fluoro-3.4-dihvdro-2(1H)-isoquinolinecarboxylate; EPO <DP n="54"/>A suspension of 1 ,1-dimethylethyl 7-fluoro-6-nitro-3,4-dihydro-2(1 H)- isoquinolinecarboxylate (Intermediate 39) (2.8Og) in EtOH (200ml) was hydrogenated at atmospheric pressure in the presence of 10% palladium on charcoal (wet) (800mg) for 3h, filtered and evaporated to a dark oil. The oil was azeotroped with DCM to give the title compound as a dark oil (2.38g). Mass spectrum : Found MH+ 267 H.p.l.c. R, 3.00min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: sulfuric acid / acetic acid / 20 °C 2.1: sodium nitrate 2.2: 0 - 5 °C 3.1: hydrogenchloride; water / methanol / Heating 4.1: triethylamine / 1,4-dioxane / 20 °C 5.1: palladium on carbon; hydrogen / ethanol / 20 °C | ||
Multi-step reaction with 5 steps 1: sulfuric acid; acetic acid / 20 h / 20 °C 2: sulfuric acid; potassium nitrate / 2 h / 0 - 4 °C 3: hydrogenchloride; methanol; water / 11 h / Heating / reflux 4: triethylamine / 1,4-dioxane; water / 22 h / 20 °C 5: hydrogen / palladium 10% on activated carbon / ethanol / 3 h / 760.05 Torr | ||
Multi-step reaction with 5 steps 1: sulfuric acid; acetic acid / 4 h / 20 °C 2: sulfuric acid; potassium nitrate / 2 h / 0 °C 3: hydrogenchloride; methanol / water / 1 h / 60 °C 4: potassium carbonate / acetonitrile / 1 h / 60 °C 5: palladium on activated charcoal; hydrazine hydrate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride; water / methanol / Heating 2: triethylamine / 1,4-dioxane / 20 °C 3: palladium on carbon; hydrogen / ethanol / 20 °C | ||
Multi-step reaction with 3 steps 1: hydrogenchloride; methanol; water / 11 h / Heating / reflux 2: triethylamine / 1,4-dioxane; water / 22 h / 20 °C 3: hydrogen / palladium 10% on activated carbon / ethanol / 3 h / 760.05 Torr | ||
Multi-step reaction with 3 steps 1: hydrogenchloride; methanol / water / 1 h / 60 °C 2: potassium carbonate / acetonitrile / 1 h / 60 °C 3: palladium on activated charcoal; hydrazine hydrate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20 °C 2: methyl iodide / acetonitrile / 20 °C 3: caesium carbonate / acetonitrile / 60 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20 °C 2: methyl iodide / acetonitrile / 20 °C 3: caesium carbonate / acetonitrile / 60 °C 4: 20 % Pd(OH)2/C; hydrogen / ethanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20 °C 2: methyl iodide / acetonitrile / 20 °C 3: caesium carbonate / acetonitrile / 60 °C 4: 20 % Pd(OH)2/C; hydrogen / ethanol / 20 °C 5: pyridine / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20 °C 2: methyl iodide / acetonitrile / 20 °C 3: caesium carbonate / acetonitrile / 60 °C 4: 20 % Pd(OH)2/C; hydrogen / ethanol / 20 °C 5: pyridine / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20 °C 2: methyl iodide / acetonitrile / 20 °C 3: caesium carbonate / acetonitrile / 60 °C 4: 20 % Pd(OH)2/C; hydrogen / ethanol / 20 °C 5: pyridine / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20 °C 2: methyl iodide / acetonitrile / 20 °C 3: caesium carbonate / acetonitrile / 60 °C 4: 20 % Pd(OH)2/C; hydrogen / ethanol / 20 °C 5: pyridine / acetonitrile / 20 °C 6: hydrogenchloride / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20 °C 2: methyl iodide / acetonitrile / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20 °C 2: methyl iodide / acetonitrile / 20 °C 3: caesium carbonate / acetonitrile / 60 °C 4: 20 % Pd(OH)2/C; hydrogen / ethanol / 20 °C 5: pyridine / acetonitrile / 20 °C 6: hydrogenchloride / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 20 °C 2: methyl iodide / acetonitrile / 20 °C 3: caesium carbonate / acetonitrile / 60 °C 4: 20 % Pd(OH)2/C; hydrogen / ethanol / 20 °C 5: pyridine / acetonitrile / 20 °C 6: hydrogenchloride / methanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / 1,4-dioxane / 20 °C 2: palladium on carbon; hydrogen / ethanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / 1,4-dioxane / 20 °C 2: palladium on carbon; hydrogen / ethanol / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1.1: triethylamine / dichloromethane / -5 - 0 °C 2.1: sulfuric acid / acetic acid / 20 °C 3.1: sodium nitrate 3.2: 0 - 5 °C 4.1: hydrogenchloride; water / methanol / Heating 5.1: triethylamine / 1,4-dioxane / 20 °C 6.1: palladium on carbon; hydrogen / ethanol / 20 °C | ||
Multi-step reaction with 6 steps 1: triethylamine / dichloromethane / 1.67 h / -5 - 8 °C 2: sulfuric acid; acetic acid / 20 h / 20 °C 3: sulfuric acid; potassium nitrate / 2 h / 0 - 4 °C 4: hydrogenchloride; methanol; water / 11 h / Heating / reflux 5: triethylamine / 1,4-dioxane; water / 22 h / 20 °C 6: hydrogen / palladium 10% on activated carbon / ethanol / 3 h / 760.05 Torr | ||
Multi-step reaction with 6 steps 1: triethylamine / water; dichloromethane / 0.5 h / 20 °C 2: sulfuric acid; acetic acid / 4 h / 20 °C 3: sulfuric acid; potassium nitrate / 2 h / 0 °C 4: hydrogenchloride; methanol / water / 1 h / 60 °C 5: potassium carbonate / acetonitrile / 1 h / 60 °C 6: palladium on activated charcoal; hydrazine hydrate |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 16h; | 2 Step-2: Preparation of tert-butyl 6-( I -(3-cyanophenyl)-3 -(trifluorornethyl)- 1 H-pyrazole-5- carboxarnido)-7-fluoro-3 ,4-dihydroisoquinoline-2( 1 H)-carboxylate (16.1 c) To a solution of I -(3-cyanophenyl)-3-(trifluorornethyl)- I H-pyrazole-5-carboxylic acid (91) (0.250 g, 0.889 mmol) in N,N-dimethylformamide (6 mL) was added tert-butyl 6- amino-7-fluoro-3,4-dihydroisoquinoline-2( 1 H)-carboxylate (161 b) (0.237 g, 0.889 rnmol), N-ethyl-N-isopropylpropan-2-amine (I .239 m L, 7. II mmol) and Bromo-tri s-pyrrol idino phosphoniumhexafluorophosphate (PyBroP) (0.456 g, 0.978 mmol) at room temperature.The resulting reaction mixture was stirred at 20 °C for 16 h. The reaction mixture was quenched with water (25 mL) and extracted with ethyl acetate (50 rnL, 20 mL, 20 mL). The organic layers were combined washed with water (25 mL), brine (25 mL), dried over MgSO4, filtered, concentrated in vacuum to dryness. The residue purified by flash column chromatography (silica gel 25 g, eluting with hexanes in ethyl acetate from 0-100%) tofurnish tert-butyl 6-( I -(3-cyanophenyl)-3-(trifluorornethyl)- I H-pyrazole-5-carboxamido)-7-fiuoro-3,4-dihydroisoquinoline-2(lH)-carboxylate (161c) (235 mg, 50% yield) as a whitesolid; ‘H NMR (300 MHz, DMSO-d6) 6 10.51 (s, IH, D20 exchangeable), 8.12 (t, J 1.9liz, 1K), 8.00 (dt, J = 7.7, 1.3 liz, IN), 7.95-7.85 (m, 1K), 7.80-7.68 (m, 21-1), 7.35 (d, J7.7 Hz, IH), 7.18 (d, J 11.2Hz, 111), 4.48 (s, 2H), 3.53 (t, J = 5.9 Hz, 2H), 2.720. J = 5.8Hz, 2H), 1.42 (s, 914); “F NMR (282 MHz, DMSO-d6) 6 -59.40 - -62.27 (m), -125.03; MS(ES-): 527.7 (M-1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C 2: methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate / 0.33 h / 20 °C / Cooling with ice |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 16 h / 20 °C 2: methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate / 0.33 h / 20 °C / Cooling with ice 3: hydrogenchloride / 1,4-dioxane / 14 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.5 g | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 7h; | 3 tert-Butyl 7-fluoro-6-([1-(3,4,5-trifluorobenzyl)-1H-imidazol-4-yl]carbonyl}amino)-3,4-dihydroisoquinoline-2(1H)-carboxylate To a solution of the compound of Reference Example 1-2 (897 mg) in DMF (15 mL) were added tert-butyl 6-amino-7-fluoro-3,4-dihydroisoquinoline-2(1H)-carboxylate (932 mg), EDCI·HCl (805 mg), HOBt (567 mg) and N,N-diisopropylethylamine(1.22 mL), and the mixture was stirred at 80°C for 7 hours. To the reaction mixture was added waterand then aqueous sodium hydroxide, and the mixture was extracted with chloroform. The organic layer was washedwith brine, dried over magnesium sulfate, filtered, and then concentrated in vacuo. The residue was purified by silicagel column chromatography (chloroform/methanol) to give the title compound (1.50 g).LC-MS ([M+H]+/Rt (min)): 505.3/1.137 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / 1,4-dioxane; water / 22 h / 20 °C 2: hydrogen / palladium 10% on activated carbon / ethanol / 3 h / 760.05 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In toluene at 100℃; for 3h; | S42.1 Step-1: Synthesis of tert-butyl 6-((6-cyano-8-cyclopentyl-7-oxo-7,8- dihydropyrido[2,3-d]pyrimidin-2-yl)amino)-7-fluoro-3,4-dihydroisoquinoline-2(1H)- carboxylate To a stirred solution of 8-cyclopentyl-2-(methylsulfinyl)-7-oxo-7,8- dihydropyrido[2,3-d]pyrimidine-6-carbonitrile (100 mg, 0.33 mmol, 1 equiv) in toluene (5 mL), was added tert-butyl 6-amino-7-fluoro-3,4-dihydroisoquinoline-2(1H)-carboxylate (96 mg, 0.36 mmol, 1.1 equiv). The resultant reaction mixture was allowed to stir at 100 °C for 3h. Progress of the reaction was monitored by LCMS. After completion of the reaction, solid observed was filtered and dried under vacuum to obtain crude compound, which was purified by recrystallization with methanol to obtain desired product. LCMS: 505 [M+H] + |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: potassium carbonate / acetonitrile / 1 h / 60 °C 2: palladium on activated charcoal; hydrazine hydrate |
[ 912846-67-4 ]
tert-Butyl 7-fluoro-6-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.86
[ 1192874-45-5 ]
(S)-Di-tert-Butyl 2-(4-fluoro-2-methylphenyl)piperazine-1,4-dicarboxylate
Similarity: 0.83
[ 334477-42-8 ]
tert-Butyl 3-(4-fluoro-2-methylphenyl)piperazine-1-carboxylate
Similarity: 0.83
[ 164148-92-9 ]
tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.86
[ 171049-41-5 ]
tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.86
[ 912846-67-4 ]
tert-Butyl 7-fluoro-6-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.86
[ 1159822-30-6 ]
tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate hydrochloride
Similarity: 0.85
[ 645418-66-2 ]
tert-Butyl 7-amino-4,4-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.84
[ 164148-92-9 ]
tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.86
[ 171049-41-5 ]
tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.86
[ 1159822-30-6 ]
tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate hydrochloride
Similarity: 0.85
[ 645418-66-2 ]
tert-Butyl 7-amino-4,4-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.84
[ 164148-92-9 ]
tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.86
[ 171049-41-5 ]
tert-Butyl 7-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.86
[ 912846-67-4 ]
tert-Butyl 7-fluoro-6-nitro-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.86
[ 1159822-30-6 ]
tert-Butyl 6-amino-3,4-dihydroisoquinoline-2(1H)-carboxylate hydrochloride
Similarity: 0.85
[ 645418-66-2 ]
tert-Butyl 7-amino-4,4-dimethyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
Similarity: 0.84