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[ CAS No. 108575-32-2 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 108575-32-2
Chemical Structure| 108575-32-2
Structure of 108575-32-2 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 108575-32-2 ]

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Product Details of [ 108575-32-2 ]

CAS No. :108575-32-2 MDL No. :MFCD09749829
Formula : C6H12ClN Boiling Point : -
Linear Structure Formula :- InChI Key :SKTAYCACHOHBEU-UHFFFAOYSA-N
M.W : 133.62 Pubchem ID :12232990
Synonyms :

Calculated chemistry of [ 108575-32-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.83
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.32
Log Po/w (WLOGP) : 1.63
Log Po/w (MLOGP) : 1.74
Log Po/w (SILICOS-IT) : 0.54
Consensus Log Po/w : 1.05

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.43
Solubility : 4.92 mg/ml ; 0.0368 mol/l
Class : Very soluble
Log S (Ali) : -1.47
Solubility : 4.55 mg/ml ; 0.0341 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.75
Solubility : 23.9 mg/ml ; 0.179 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.75

Safety of [ 108575-32-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 108575-32-2 ]

* 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 [ 108575-32-2 ]

[ 108575-32-2 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 108575-32-2 ]
  • [ 122-04-3 ]
  • [ 202146-07-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In dichloromethane 1.3 EXAMPLES 1-3 EXAMPLES 1-3 In a three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 4 grams (g) (0.03 mole) of 3-amino-3-methyl-1-pentyne hydrochloride (4 grams (g) (0.03 mole) suspended in 100 milliliters (mL) of methylene chloride in a three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer. Triethylamine (6.82 g, 9.4 mL) was added slowly, keeping the temperature between 5° C. and 10° C. 4-nitrobenzoyl chloride 5 g (0.027 mole) was added to the resulting mixture at a rate to keep the reaction temperature between 5° C. and 10° C. After the addition was complete the reaction mixture was stirred at room temperature for 0.5 hours, and was then sequentially washed with water (2*100 mL), 5% aqueous hydrochloric acid, (2*100 mL), water (1*50 mL), 5% aqueous sodium hydroxide (2*100 mL) and finally with water (1*100 mL) before being dried over anhydrous magnesium sulfate. The solvent was removed in the rotary evaporator, yielding N-(3-methylpent-1-yn-3-yl)-4-nitrobenzamide, used as such in the next step. In a 500 mL, three-necked, round-bottomed flask fitted with a mechanical stirrer, thermometer and addition funnel were placed 6.7 grams of the previously prepared N-(3-methylpent-1-yn-3-yl)-4-nitrobenzamide and 120 mL of methylene chloride.
  • 2
  • [ 108575-32-2 ]
  • [ 60-29-7 ]
  • [ 202146-14-3 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine; trifluoroacetic anhydride In tetrahydrofuran; <i>N</i>-methyl-acetamide; water 10 EXAMPLE 10 EXAMPLE 10 In a 125 mL, three-necked, round-bottomed flask fitted with a mechanical stirrer nitrogen inlet and thermometer were placed 13.4 g (0.1 mole) of 3-methyl-1-pentyn-3-amine hydrochloride, 45 mL dimethylformamide and cooled down to 0° C. To the resulting well-stirred mixture was added slowly 20.2 g (0.2 mole) of triethylamine dropwise, keeping the temperature below 3° C. After the addition was completed, the reaction mixture was stirred 15 minutes followed by dropwise addition of 18.9 g (0.09 mole) of trifluoroacetic anhydride dissolved in 35 mL of tetrahydrofuran at such a rate to keep the reaction temperature below 3° C. After the addition was completed, the reaction mixture was stirred at room temperature overnight and then poured into a mixture of 100 mL of water and 100 mL of ethyl ether. The lower phase was discarded, the organic layer was washed sequentially with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, treated with activated charcoal and then filtered through celite. The solvent was then eliminated under reduced pressure, yielding 12.1 g (70% yield) N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide as a white solid.
  • 3
  • [ 108575-32-2 ]
  • [ 202146-14-3 ]
YieldReaction ConditionsOperation in experiment
255.5 g (83%) With triethylamine; trifluoroacetic anhydride In dichloromethane; pentane 3.a a) a) Preparation of N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide In a 3 liter, four-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer was placed 234 g (1.75 mole) of 3-amino-3-methyl-1-pentyne hydrochloride and 1,000 mL of methylene chloride. To the resulting well-stirred mixture was added slowly 354 g (3.51 mole) of triethylamine (TEA) dropwise, keeping the temperature below 30°-- C. After the addition was completed, the reaction mixture was stirred 120 minutes followed by dropwise addition of 334.5 g (1.59 mole) of trifluoroacetic anhydride dissolved in 500 mL of methylene chloride at such a rate to keep the reaction temperature at 0°-- C. After the addition was completed the reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The resulting slurry was washed with ethyl ether. The ethyl ether layer was washed sequentially with water, saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, treated with activated charcoal, and filtered through Celite. The solvent was eliminated under reduced pressure. The resulting crude product was treated with cold pentane, filtered, and dried yielding 255.5 g (83%) of the expected N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide as a white solid.
255.5 g (83%) With triethylamine; trifluoroacetic anhydride In dichloromethane; pentane i i) i) Preparation of N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide In a 3 liter, four-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer was placed 234 grams (g) (1.75 mole) of 3-amino-3-methyl-1-pentyne hydrochloride and 1,000 mL of methylene chloride. To the resulting well-stirred mixture was added slowly 354 g (3.51 mole) of triethylamine (TEA) dropwise, keeping the temperature below 30° C. After the addition was completed, the reaction mixture was stirred 120 minutes followed by dropwise addition of 334.5 g (1.59 mole) of trifluoroacetic anhydride dissolved in 500 mL of methylene chloride at such a rate to keep the reaction temperature at 0° C. After the addition was completed the reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The resulting slurry was washed with ethyl ether. The ethyl ether layer was washed sequentially with water, saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, treated with activated charcoal, and filtered through Celite filter agent (available from Aldrich Chemical Company, St. Louis, Mo.). The solvent was eliminated under reduced pressure. The resulting crude product was treated with cold pentane, filtered, and dried yielding 255.5 g (83%) of the expected N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide as a white solid.
255.5 g (83%) With triethylamine; trifluoroacetic anhydride In dichloromethane; pentane 1.a a a N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide In a 3000 milliliter (ml) four-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet, and thermometer a mixture was made of 234 grams (g) (1.75 mole) of 3-methyl-1-pentyn-3-amine hydrochloride and 1000 ml of methylene chloride. The mixture was stirred thoroughly and 354 g (3.51 mole) of triethylamine (TEA) were added dropwise, with the temperature maintained below 30° C. After the addition was completed the reaction mixture was stirred 120 minutes followed by dropwise addition of a solution containing 334.5 g (1.59 mole) of trifluoroacetic anhydride in 500 ml of methylene chloride. The addition was made at such a rate that the temperature was maintained at 0° C. After the addition was completed the reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The resulting slurry was washed with ethyl ether. The ethyl ether layer was washed sequentially with water, saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, treated with activated charcoal, and filtered through a filter agent (Celite, 95% SiO2, from Aldrich Chemical Co., Milwaukee Wis.). The solvent was eliminated in a rotary evaporator. The resulting crude product was treated with cold pentane, filtered and dried, yielding 255.5 g (83%) of the expected N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide as a white solid.
255.5 g (83%) With triethylamine; trifluoroacetic anhydride In dichloromethane; pentane 3.a a) a) Preparation of N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide In a 3 liter, four-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer was placed 234 g (1.75 mole) of 3-amino-3-methyl-1-pentyne hydrochloride and 1,000 mL of methylene chloride. To the resulting well-stirred mixture was added slowly 354 g (3.51 mole) of triethylamine (TEA) dropwise, keeping the temperature below 30 °C. After the addition was completed, the reaction mixture was stirred 120 minutes followed by dropwise addition of 334.5 g (1.59 mole) of trifluoroacetic anhydride dissolved in 500 mL of methylene chloride at such a rate to keep the reaction temperature at 0°C. After the addition was completed the reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The resulting slurry was washed with ethyl ether. The ethyl ether layer was washed sequentially with water, saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, treated with activated charcoal, and filtered through Celite. The solvent was eliminated under reduced pressure. The resulting crude product was treated with cold pentane, filtered, and dried yielding 255.5 g (83%) of the expected N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide as a white solid.
255.5 g (83%) With triethylamine; trifluoroacetic anhydride In dichloromethane; pentane i i) i) Preparation of N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide In a 3 liter, four-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer was placed 234 grams (g) (1.75 mole) of 3-amino-3-methyl-1-pentyne hydrochloride and 1,000 mL of methylene chloride. To the resulting well-stirred mixture was added slowly 354 g (3.51 mole) of triethylamine (TEA) dropwise, keeping the temperature below 30 °C. After the addition was completed, the reaction mixture was stirred 120 minutes followed by dropwise addition of 334.5 g (1.59 mole) of trifluoroacetic anhydride dissolved in 500 mL of methylene chloride at such a rate to keep the reaction temperature at 0 °C. After the addition was completed the reaction mixture was stirred at room temperature overnight and concentrated in vacuo. The resulting slurry was washed with ethyl ether. The ethyl ether layer was washed sequentially with water, saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, treated with activated charcoal, and filtered through Celite. The solvent was eliminated under reduced pressure. The resulting crude product was treated with cold pentane, filtered, and dried yielding 255.5 g (83%) of the expected N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide as a white solid.
255.5 g (83%) With triethylamine; trifluoroacetic anhydride In dichloromethane; pentane i i) i) Preparation of N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide In a 3 liter, four-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer was placed 234 grams (g) (1.75 mole) of 3-amino-3-methyl-1-pentyne hydrochloride and 1,000 mL of methylene chloride. To the resulting well-stirred mixture was added slowly 354 g (3.51 mole) of triethylamine (TEA) dropwise, keeping the temperature below 30 °C. After the addition was completed, the reaction mixture was stirred 120 minutes followed by dropwise addition of 334.5 g (1.59 mole) of trifluoroacetic anhydride dissolved in 500 mL of methylene chloride at such a rate to keep the reaction temperature at 0 °C. After the addition was completed the reaction mixture was stirred at room temperature overnight and concentrated in vacuo.The resulting slurry was washed with ethyl ether. The ethyl ether layer was washed sequentially with water, saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, treated with activated charcoal, and filtered through Celite filter agent (available from Aldrich Chemical Company, St. Louis, MO). The solvent was eliminated under reduced pressure. The resulting crude product was treated with cold pentane, filtered, and dried yielding 255.5 g (83%) of the expected N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide as a white solid.
255.5 g (83%) With triethylamine; trifluoroacetic anhydride In dichloromethane; pentane i i) i) Preparation of N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide In a 3 liter, four-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer was placed 234 grams (g) (1.75 mole) of 3-amino-3-methyl- 1-pentyne hydrochloride and 1,000 mL of methylene chloride. To the resulting well-stirred mixture was added slowly 354 g (3.51 mole) of triethylamine (TEA) dropwise, keeping the temperature below 30 °C. After the addition was completed, the reaction mixture was stirred 120 minutes followed by dropwise addition of 334.5 g (1.59 mole) of trifluoroacetic anhydride dissolved in 500 mL of methylene chloride at such a rate to keep the reaction temperature at 0 °C. After the addition was completed the reaction mixture was stirred at room temperature overnight and concentrated in vacuo.The resulting slurry was washed with ethyl ether. The ethyl ether layer was washed sequentially with water, saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, treated with activated charcoal, and filtered through Celite filter agent (available from Aldrich Chemical Company, St. Louis, MO). The solvent was eliminated under reduced pressure. The resulting crude product was treated with cold pentane, filtered, and dried yielding 255.5 g (83%) of the expected N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide as a white solid.

  • 4
  • [ 202146-14-3 ]
  • [ 108575-32-2 ]
  • [ CAS Unavailable ]
  • [ 202195-53-7 ]
YieldReaction ConditionsOperation in experiment
With chlorine; triethylamine; trifluoroacetic anhydride In tetrahydrofuran; <i>N</i>-methyl-acetamide; dichloromethane 10 EXAMPLE 10 The above described reaction was repeated using 231 g (1.1 mole) of trifluoroacetic anhydride, 163 g (1.2 mole) of 3-methyl-1-pentyn-3-amine hydrochloride, 247 g (2.4 mole) of triethylamine, 500 mL tetrahydrofuran and 500 mL of dimethylformamide, yielding 168.3 g N-[3-(3-methyl-1-pentynyl)]trifluoroacetamide. In a 1 L, three-necked, round-bottomed flask fitted with a mechanical stirrer, a thermometer and a 100 mL addition funnel, 11.4 g, (59 mole) of N-[3-3-methyl-1-pentynyl)]trifluoroacetamide was dissolved in 200 mL of methylene chloride. The resulting mixture was cooled to -30° C and a 10.7 g of chlorine were bubbled in over a 0.5 hour period. When the addition was completed the reaction mixture was stirred at -30° C. for 30 minutes, then warmed to room temperature and stirred for 3 hours. The solvent was then removed from the crude reaction mixture using a rotary evaporator, yielding 2-trifluoromethyl-4-methyl-4-ethyl-5-chloro-5-(dichloromethyl)-oxazoline hydrochloride, which was used as such in the next step.
  • 5
  • 3-amino-3-methyl-1-pentynyl hydrochloride [ No CAS ]
  • methane sulfonyl chloride [ No CAS ]
  • [ 3113-71-1 ]
  • N-(3-methylpent-1-yn-3-yl)-3-methyl-4-nitrobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran; dichloromethane; water; ethyl acetate 9 EXAMPLE 9 EXAMPLE 9 In a 500 mL, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 10 g of 3-methyl-4-nitrobenzoic acid, 200 mL of tetrahydrofuran and 38 mL triethylamine were added to The resulting well-stirred mixture was cooled to -30° C. and 4.7 mL of methane sulfonyl chloride were added dropwise keeping the reaction temperature at -30° C. The resulting suspension was stirred at -30° C. during 30 minutes, after which 8.1 g of 3-amino-3-methyl-1-pentyne hydrochloride were added slowly over a 20 minute period. After the addition was complete the reaction mixture was stirred at -30° C. for an additional 30 minutes. The reaction mixture was then poured into a mixture of 400 mL water and 200 mL of ethyl acetate. The phases were separated and the aqueous layer was extracted with ethyl acetate (2*150 mL). The combined organic phases were washed sequentially with water (1*200 mL), 5% aqueous hydrochloric acid (2*200 mL), water (1*200 mL), 5% aqueous sodium hydroxide (2*200 mL) and finally with water (1*200 mL) and then dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator, yielding the crude product. The crude product was dissolved in 100 mL of methylene chloride and filtered through a small silica gel column yielding 4.11 g of N-(3-methylpent-1-yn-3-yl)-3-methyl-4-nitrobenzamide.
  • 6
  • 3-amino-3-methyl-1-pentynyl hydrochloride [ No CAS ]
  • [ 41668-11-5 ]
  • methane sulfonyl chloride [ No CAS ]
  • N-(3-methylpent-1-yn-3-yl)-6-amino-5-chloronicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran EXAMPLES 12 AND 13 EXAMPLES 12 AND 13 In a 300 mL, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 5 g (0.03 mole) of 6-amino-5-chloronicotinic acid, 150 mL of tetrahydrofuran and 6.67 g (0.066 mole) of triethylamine. The resulting well-stirred mixture was cooled to -30° C. and 2.24 ml (0.03 mole) of methane sulfonyl chloride were added dropwise keeping the reaction temperature at -30° C. The resulting suspension was stirred at -30° C. during 30 minutes, after which 4.01 g (0.03 mole) of 3-amino-3-methyl-1-pentyne hydrochloride were added slowly over a 20 minute period. After the addition was completed, the reaction mixture was stirred at -30° C. for an additional 30 minutes. The reaction mixture was poured into water and extracted with methylene chloride (3*450 ml). The combined organic phases were washed with water (1*200 ml), and dried over anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator, yielding the crude product. After purification by chromatographic column (silica gel, 1:1 ethyl acetate:hexane), 3.25 g N-(3-methylpent-1-yn-3-yl)-6-amino-5-chloronicotinamide were obtained as a white solid.
  • 7
  • 3-amino-3-methyl-1-pentynyl hydrochloride [ No CAS ]
  • methane sulfonyl chloride [ No CAS ]
  • [ 1539-06-6 ]
  • N-(3-methylpent-1-yn-3-yl)-4-acetamido-3-nitrobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; water; ethyl acetate; EXAMPLE 8 In a 1000 mL, three-necked, round-bottomed flask fitted with a mechanical stirrer, nitrogen inlet and thermometer were placed 10 g of <strong>[1539-06-6]4-acetamido-3-nitrobenzoic acid</strong>, 200 mL of tetrahydrofuran and 31 mL of triethylamine. The resulting well-stirred mixture was cooled to -30 C. and 3.9 mL of methane sulfonyl chloride were added dropwise while keeping the reaction temperature at -30 C. The resulting suspension was stirred at -30 C. for 30 minutes, after which 6.7 g of 3-amino-3-methyl-1-pentyne hydrochloride were added slowly over a 20 minute period. After the addition was complete, the reaction mixture was stirred at -30 C. for an additional 30 minutes. The reaction mixture was then poured into a mixture of 400 mL water and 200 mL of ethyl acetate. The phases were separated and the aqueous layer was then extracted with ethyl acetate (2*150 mL). The combined organic phases were washed sequentially with water (1*200 mL), 5% aqueous hydrochloric acid (2*200 mL), water (1*200 mL), 2% aqueous sodium hydroxide (2*200 mL) and water (1*200 mL) and then dried over anhydrous magnesium sulfate. The solvent was removed in the rotary evaporator, yielding 8.2 g of N-(3-methylpent-1-yn-3-yl)-4-acetamido-3-nitrobenzamide. In a 500 mL, three-necked, round-bottomed flask fitted with a mechanical stirrer, a thermometer and addition funnel, the N-(3-methylpent-1-yn-3-yl)-4-acetamido-3-nitrobenzaide preapared in the preceeding step was dissolved in 180 mL of methylene chloride.
  • 8
  • [ 108575-32-2 ]
  • [ 153203-60-2 ]
  • [ 593-56-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran; <i>N</i>-methyl-acetamide 9.m m) To a cooled, well stirred mixture of 3-methyl-1-pentyn-3-amine hydrochloride (47.2 g, 0.354 moles), and dimethylformamide (74 ml) was added dropwise triethylamine (71.5 g, 0.71 mole) over 30 minutes. When the addition was completed, the resulting mixture was stirred another 30 minutes at 0° C. To the resulting mixture was added dropwise a solution of 3-formyl-5-chlorobenzoyl chloride (74 g, approx. 0.36 mole) dissolved in tetrahydrofuran (65 ml), keeping the temperature between 5° to 10° C. When the addition was completed, the resulting mixture was stirred another 6 hours at room temperature. To the well stirred mixture were added dropwise a solution of methoxylamine hydrochloride (30.7 g, 0.369 mole) in dimethylformamide (165 ml) at room temperature, followed by the dropwise addition of triethylamine (37.2 g, 0.369 mole), all the while keeping the temperature below 20° C. The resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into ice-water (1 liter) and extracted with ethyl acetate (3*400 ml). The combined organic layers were washed with water (2*300 ml), then with 5% aqueous sodium bicarbonate (2*300 ml) and then with brine (1*400 ml) and then dried over anhydrous sodium sulfate. The solvent was then eliminated in a rotavap yielding 69.3 g of N-(3-methylpent-1-yne)-3-methoxyiminomethyl-5-methylbenzamide, used as such in the next step.
  • 9
  • [ 108575-32-2 ]
  • [ 75650-38-3 ]
  • [ 593-56-6 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran; <i>N</i>-methyl-acetamide 1.b b) b) Preparation of N-(3-Methylpent-1-yne)-3-methoxyiminomethylbenzamide To a cooled, well stirred mixture of 3-methyl-1-pentyn-3-amine hydrochloride (76.6 g, 0.57 moles), and dimethylformamide (500 ml) was added dropwise triethylamine (117 g, 1.147 mole) over 30 minutes. When the addition was completed, the resulting mixture was stirred another 30 minutes at 0° C. To the resulting mixture was added dropwise a solution of 3-formyl-benzoyl chloride (96.5 g, approx. 0.57 mole) dissolved in tetrahydrofurane (100 ml), keeping the temperature between 5° to 10° C. When the addition was completed, the resulting mixture was stirred another 1 hour at room temperature. To the well stirred mixture was added (dropwise) a solution of methoxylamine hydrochloride (47.8 g, 0.57 mole) in dimethylformamide (275 ml) at room temperature, followed by the dropwise addition of triethylamine (58.3 g, 0.57 mole) all the while keeping the temperature below 20° C. The resulting mixture was stirred overnight at room temperature. The reaction mixture was poured into ice-water (1 liter) and extracted with ethyl acetate (3*400 ml). The combined organic layers were washed with water (2*300 ml), then with 5% aqueous sodium bicarbonate (2*300 ml), and then with brine (1*400 ml), and dried over anhydrous sodium sulfate. The solvent was then eliminated in a rotavap yielding 121.3 g of N-(3-methylpent-1-yne)-3-methoxyiminomethylbenzamide as an oil used as such in the next step.
  • 10
  • [ 108575-32-2 ]
  • [ 407-25-0 ]
  • [ 202146-14-3 ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: 3-amino-3-methyl-1-pentynyl hydrochloride With triethylamine In dichloromethane at 30℃; for 2h; Stage #2: trifluoroacetic anhydride In dichloromethane at 0 - 20℃;
83% Stage #1: 3-amino-3-methyl-1-pentynyl hydrochloride With triethylamine In dichloromethane at 30℃; for 2h; Stage #2: trifluoroacetic anhydride In dichloromethane at 0 - 20℃;
  • 11
  • [ 108575-32-2 ]
  • [ 894792-94-0 ]
  • [ 2088617-71-2 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
34.7% Stage #1: 3-amino-3-methyl-1-pentynyl hydrochloride; 4-(tert-butoxy)-3-(2-(2-(2-methoxyphenyl)acetamido)-3-methylbutanamido)-4-oxobutanoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 6h; Stage #2: 1-azido-2-fluoroethane With CuSO4*2H2O; ascorbic acid; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine In N,N-dimethyl-formamide at 25℃;
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