Alternatived Products of [ 1174068-79-1 ]
Product Details of [ 1174068-79-1 ]
| CAS No. : | 1174068-79-1 |
MDL No. : | MFCD13195336 |
| Formula : |
C13H18N2O3
|
Boiling Point : |
- |
| Linear Structure Formula : | - |
InChI Key : | LDGNAVIMUAPFKH-UHFFFAOYSA-N |
| M.W : |
250.29
|
Pubchem ID : | 57786812 |
| Synonyms : |
|
Safety of [ 1174068-79-1 ]
Application In Synthesis of [ 1174068-79-1 ]
* 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 [ 1174068-79-1 ]
- 1
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[ 626-55-1 ]
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[ 1174068-79-1 ]
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[ 1174068-94-0 ]
| Yield | Reaction Conditions | Operation in experiment |
| 30% |
Stage #1: 3-Bromopyridine With n-butyllithium In diethyl ether at -78℃; for 0.5h;
Stage #2: C13H18N2O3 In diethyl ether at -78 - 25℃; for 16h; |
To a solution of n-BuLi (1.57 M, 2.54 ml, 4 mmol) in dry ether (5 ml) at -78° C. was added 3-bromo pyridine (4 mmol) and the reaction mixture was allowed to stir at the same temperature for 30 minutes. To it aldehyde (4 mmol) obtained from step-1 in dry ether (10 ml) was added drop wise and the resulting reaction mixture was allowed to stir at 25° C. for 16 hrs (monitored by TLC). Reaction was quenched with water, extracted with ethyl acetate, combined organic layer was washed with brine and finally dried over sodium sulfate. Evaporation of organic layer under reduced pressure gave the crude product which was purified by column chromatography (3% methanol in dichlormethane). Yield: 30% |
|
Stage #1: 3-Bromopyridine With n-butyllithium In diethyl ether at -78℃; for 0.5h;
Stage #2: C13H18N2O3 In diethyl ether at 25℃; for 16h;
Stage #3: With water In diethyl ether |
Procedure for step-2 :To a solution of n-BuLi (1.57 M, 2.54 ml, 4 mmol) in dry ether (5 ml) at -780C was added 3-bromo pyridine (4 mmol) and the reaction mixture was allowed to stir at the same temperature for 30 minutes. To it aldehyde (4 mmol) obtained from step-1 in dry ether (10 ml) was added drop wise and the resulting reaction mixture was allowed to stir at 25°C for 16 hrs (monitored by TLC) . Reaction was quenched with water, extracted with ethyl acetate, combined organic layer was washed with brine and finally dried over sodium sulfate. Evaporation of organic layer under reduced pressure gave the crude product which was purified by column chromatography (3% methanol in dichlormethane) . Yield: 30% |
- 2
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[ 75-52-5 ]
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[ 1174068-79-1 ]
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[ 1174068-83-7 ]
| Yield | Reaction Conditions | Operation in experiment |
|
With ammonium acetate for 2h; Heating / reflux; |
Ammonium acetate (0.45 equiv.) was added to a solution of the aldehyde (10.4 mmole) in nitromethane (14.5 ml). The reaction mixture was then heated under reflux for 2 hours (DC check). After completion of the reaction the nitromethane was carefully removed under reduced pressure. The residue was taken up in ethyl acetate and washed successively with water and saturated sodium chloride solution. The organic phase was dried over sodium sulfate and the solvent was removed on a rotary evaporator. The crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate 9:1). |
|
With ammonium acetate for 2h; Reflux; |
1
Preparation of the amine building blocks A36 and A37 The preparation of the aldehyde reacted in Stage 1 was carried out according to Stage 1 of the synthesis of the building blocks A33 and A34.Stage 1. Ammonium acetate (0.45 equiv.) was added to a solution of the aldehyde (10.4 mmole) in nitromethane (14.5 ml) . The reaction mixture was then heated under reflux for 2 hours (DC check) . After completion of the reaction the nitromethane was carefully removed under reduced pressure. The residue was taken up in ethyl acetate and washed successively with water and saturated sodium chloride solution. The organic phase was dried over sodium sulfate and the solvent was removed on a rotary evaporator. The crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate 9:1) . |
- 3
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[ 108-89-4 ]
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[ 1174068-79-1 ]
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[ 1174284-54-8 ]
| Yield | Reaction Conditions | Operation in experiment |
| 48% |
Stage #1: picoline With n-butyllithium In tetrahydrofuran at -78 - 25℃; for 1h;
Stage #2: C13H18N2O3 In tetrahydrofuran at 0 - 25℃; for 3h;
Stage #3: With water In tetrahydrofuran |
To a solution of 4-picoline (4 mmol) in dry THF (10 ml) was added n-BuLi (1.57M, 2.5 ml, 4 mmol) at -78° C. and the resulting reaction mixture was allowed to stir at 25° C. for 1 hr. It was again cooled to 0° C. and the aldehyde obtained from step-1 (1 g, 4 mmol) was added to the reaction mixture drop wise. After stirring at 25° C. for 3 hrs, reaction mixture was quenched with water (5 ml), extracted with ethyl acetate and the combined organic layer was washed with brine. After drying over sodium sulfate, organic layer was evaporated under reduced pressure to get the crude alcohol that was purified by column chromatography (2% methanol in dichloromethane). Yield: 48% |
|
Stage #1: picoline With n-butyllithium In tetrahydrofuran at -78 - 25℃;
Stage #2: C13H18N2O3 In tetrahydrofuran at 0 - 25℃;
Stage #3: With water In tetrahydrofuran |
2
Procedure for step-2 :To a solution of 4-picoline (4 iranol) in dry THF (10 ml) was added n-BuLi (1.57M, 2.5ml, 4 mmol) at -780C and the resulting reaction mixture was allowed to stir at 250C for 1 hr. It was again cooled to 0°C and the aldehyde obtained from step-1 (Ig, 4 mmol) was added to the reaction mixture drop wise. After stirring at 25°C for 3 hrs, reaction mixture was quenched with water ( 5ml), extracted with ethyl acetate and the combined organic layer was washed with brine. After drying over sodium sulfate, organic layer was evaporated under reduced pressure to get the crude alcohol that was purified by column chromatography (2 % methanol in dichloromethane) . Yield : 48% |
- 4
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[ 29786-93-4 ]
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[ 1174068-79-1 ]
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[ 2065-66-9 ]
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[ 1174068-95-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: n-butyllithium; methyl-triphenylphosphonium iodide In tetrahydrofuran for 0.5h;
Stage #2: C13H18N2O3 In tetrahydrofuran at 0℃; for 1h; |
To an ice cold suspension of the wittig salt (4 mmol) in dry THF (25 ml) was slowly added n-BuLi (5 mmol) and the resulting reaction mixture was allowed to stir at that temperature for 30 minutes. To it aldehyde B (2 mmol) in dry THF (10 ml) was added at 0° C. and allowed to stir for further 1 hr. Reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer was washed with water and brine and finally dried over sodium sulfate. Evaporation of organic layer under reduced pressure gave the crude product that was unstable and used immediately without any further purification. |
- 5
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[ 1174068-78-0 ]
-
[ 1174068-79-1 ]
| Yield | Reaction Conditions | Operation in experiment |
| 60% |
With oxalyl dichloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane at 0 - 25℃; for 0.75h; |
A solution of oxalyl chloride (1 equiv.) in DCE (15 ml) was added to an ice-cooled solution of dry DCE (15 ml) and dry DMF (1 equiv.) and stirred for 15 minutes at RT. The solution was re-cooled to 0° C. and a solution of tert-butyl 3,4-dihydropyrrolo-[1,2-]pyrazine-2(1H)-carboxylate (5 g, 22.25 mmole) in DCE (15 ml) was added. The reaction solution was stirred for 30 minutes at this temperature (DC check). Ice was then added, followed by aqueous NaOH solution (50%). The aqueous phase was extracted with DCM and the organic phase was then washed in succession with water and satd. NaCl solution. After drying over Na2SO4, the solvent was removed in a rotary evaporator. The resulting crude product was used without further purification in the next stage; To an ice cold solution of dry DCE (15 ml) and dry DMF (1 eqv) was added a solution of oxalyl chloride (1 eqv) in dry DCE (15 ml) and the resulting reaction mixture was stirred at 25° C. for 15 minutes. Reaction was again cooled to 0° C. and to it was added a solution of 3,4-Dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester (5 gm, 22.25 mmol) in dry DCE (15 ml) and the reaction was stirred at the same temperature for 30 minutes (monitored by TLC). It was quenched with ice, 50% aqueous NaOH solution was then added, aqueous layer was extracted with DCM and the organic layer was washed successively with water and brine. After drying over sodium sulfate, organic layer was evaporated under reduced pressure to get the crude product which was used immediately in the next step without any further purification. Yield: 60% (crude) |
- 6
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[ 1174068-79-1 ]
-
[ 1174068-80-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: C13H18N2O3 With sodium hydride In tetrahydrofuran at 0 - 25℃; for 1h;
Stage #2: C13H18N2O3 In tetrahydrofuran at 0 - 25℃; for 16h; |
A solution of triethylphosphonium acetate (48.9 mmole) in dry THF (160 ml) was slowly added to a suspension of NaH (60%, 48.9 mmole) in dry THF (160 ml), cooled to 0° C., and then stirred for 60 minutes at 25° C. The reaction mixture was then cooled to 0° C. and the aldehyde (from Stage 1, 22.25 mmole) in dry THF (160 ml) was added dropwise, the temperature being maintained constant. The reaction mixture was then heated to 25° C. and stirred for 16 hours at this temperature until the reaction had gone to completion. The reaction mixture was hydrolysed first with ice and then with satd. NaCl solution. The aqueous phase was extracted with ethyl acetate. The organic phase was then washed with water and satd. NaCl solution. The organic phase was dried over Na2SO4 and the solvent was removed on a rotary evaporator. The crude product was purified by column chromatography on silica gel (solvent: DCM/ethyl acetate, 95:5). |
- 7
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[ 1174068-78-0 ]
-
[ 33513-42-7 ]
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[ 1174068-79-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: N,N-dimethyl-formamide With oxalyl dichloride In 1,2-dichloro-ethane at 20℃; Cooling with ice;
Stage #2: 3,4-Dihydro-1H-pyrrolo[1,2-a]pyrazine-2-carboxylic acid tert-butyl ester In 1,2-dichloro-ethane at 0℃; for 0.5h;
Stage #3: With water; sodium hydroxide In 1,2-dichloro-ethane Cooling with ice; |
1
Stage 1. A solution of oxalyl chloride (1 equiv.) in DCE (15 ml) was added to an ice-cooled solution of dry DCE(15 ml) and dry DMF (1 equiv.) and stirred for 15 minutes at RT. The solution was re-cooled to O0C and a solution of tert-butyl 3, 4-dihydropyrrolo [1,2-] pyrazine-2 ( IH) - carboxylate (5 g, 22.25 mmole) in DCE (15 ml) was added. The reaction solution was stirred for 30 minutes at this temperature (DC check) . Ice was then added, followed by aqueous NaOH solution (50%) . The aqueous phase was extracted with DCM and the organic phase was then washed in succession with water and saturated sodium chloride solution. After drying over sodium sulfate, the solvent was removed on a rotary evaporator. The crude product obtained was used without further purification in the next stage . |
- 8
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[ 867-13-0 ]
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[ 1174068-79-1 ]
-
[ 1174068-80-4 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0 - 25℃;
Stage #2: C13H18N2O3 In tetrahydrofuran at 0 - 25℃;
Stage #3: With water In tetrahydrofuran Cooling with ice; |
2
Stage 2. A solution of triethylphosphonium acetate(48.9 mmole) in dry THF (160 ml) was slowly added to a suspension of NaH (60%, 48.9 mmole) in dry THF (160 ml), cooled to 00C, and then stirred for 60 minutes at 25°C. The reaction mixture was then cooled to 00C and the aldehyde (from Stage 1, 22.25 mmole) in dry THF (160 ml) was added dropwise, the temperature being maintained constant. The reaction mixture was then heated to 250C and stirred for 16 hours at this temperature until the reaction had gone to completion. The reaction mixture was hydrolysed first with ice and then with saturated sodium chloride solution. The aqueous phase was extracted with ethyl acetate. The organic phase was then washed with water and saturated sodium chloride solution. The organic phase was dried over sodium sulfate and the solvent was removed on a rotary evaporator. The crude product was purified by column chromatography on silica gel (solvent: DCM/ethyl acetate, 95:5). |
- 9
-
[ 1174068-79-1 ]
-
[ 2065-66-9 ]
-
[ 1174068-95-1 ]
| Yield | Reaction Conditions | Operation in experiment |
|
Stage #1: methyl-triphenylphosphonium iodide With n-butyllithium In tetrahydrofuran for 0.5h; Cooling with ice;
Stage #2: C13H18N2O3 In tetrahydrofuran at 0℃;
Stage #3: With ammonium chloride In tetrahydrofuran; water |
2
Procedure for step-2 :To an ice cold suspension of the wittig salt (4 mmol) in dry THF (25 ml) was slowly added n-BuLi (5 mmol) and the resulting reaction mixture was allowed to stir at that temperature for 30 minutes. To it aldehyde B (2 mmol) in dry THF (10 ml) was added at 0°C and allowed to stir for further lhr. Reaction was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. Organic layer was washed with water and brine and finally dried over sodium sulfate. Evaporation of organic layer under reduced pressure gave the crude product that was unstable and used immediately without any further purification. |
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