[ CAS No. 1227694-88-3 ] {[proInfo.proName]}

Name: 1227694-88-3|(E)-N-(3-(3-(Dimethylamino)acryloyl)phenyl)-N-methylacetamide|95%
Brand: Ambeed
SKU: A103844
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Quality Control of [ 1227694-88-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 1227694-88-3 ]

Product Details of [ 1227694-88-3 ]

CAS No. :	1227694-88-3	MDL No. :	MFCD09833226
Formula :	C₁₄H₁₈N₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CWHTXVLCGAQQRA-CMDGGOBGSA-N
M.W :	246.31	Pubchem ID :	10198778
Synonyms :

Calculated chemistry of [ 1227694-88-3 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.29
Num. rotatable bonds :	5
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	72.69
TPSA :	40.62 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.86 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.55
Log Po/w (XLOGP3) :	1.33
Log Po/w (WLOGP) :	1.93
Log Po/w (MLOGP) :	1.36
Log Po/w (SILICOS-IT) :	1.45
Consensus Log Po/w :	1.72

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.12
Solubility :	1.86 mg/ml ; 0.00756 mol/l
Class :	Soluble
Log S (Ali) :	-1.78
Solubility :	4.05 mg/ml ; 0.0164 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.61
Solubility :	0.602 mg/ml ; 0.00244 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.35

Safety of [ 1227694-88-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1227694-88-3 ]

* 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 [ 1227694-88-3 ]

[ 1227694-88-3 ] Synthesis Path-Downstream 1~12

1
[ 16617-46-2 ]
[ 1227694-88-3 ]
[ 115932-13-3 ]

Yield	Reaction Conditions	Operation in experiment
60%	With hydrogenchloride In ethanol; water for 1h; Reflux;
	With acetic acid for 18h; Heating;

Reference： [1]Location in patent: experimental part Radl, Stanislav; Blahovcova, Michaela; Placek, Lukas; Pekarek, Tomas; Havlicek, Jaroslav [Journal of Heterocyclic Chemistry, 2010, vol. 47, # 2, p. 276 - 283]
[2]Andersen; Jorgensen; Braestrup [European Journal of Medicinal Chemistry, 1994, vol. 29, # 5, p. 393 - 399]

2
[ 1227694-88-3 ]
[ 159224-11-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: glacial acetic acid / 18 h / Heating 2: K₂CO₃, NH₂OH*HCl / ethanol; H₂O / 2 h / Heating

Reference： [1]Andersen; Jorgensen; Braestrup [European Journal of Medicinal Chemistry, 1994, vol. 29, # 5, p. 393 - 399]

3
[ 1227694-88-3 ]
[ 159223-97-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: glacial acetic acid / 18 h / Heating 2: K₂CO₃, NH₂OH*HCl / ethanol; H₂O / 2 h / Heating 3: glacial acetic acid / 1 h / Heating

Reference： [1]Andersen; Jorgensen; Braestrup [European Journal of Medicinal Chemistry, 1994, vol. 29, # 5, p. 393 - 399]

4
[ 1227694-86-1 ]
[ 74-88-4 ]
[ 1227694-88-3 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-acetamide With sodium hydride In N,N-dimethyl-formamide for 1h; Inert atmosphere; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 2.5h; Inert atmosphere;
72%	Stage #1: N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-acetamide With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.25h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil	1 N-[3-[3-(Dimethylamino)-1-oxo-2-pronenyl]-phenyl]-N-methyl acetamide (9). To a suspension of compound 8 (22.07 g, 95 mmol) in anhydrous dimethylformamide (114 ML) under nitrogen in an ice bath was added sodium hydride (4.75 g, 119 mmol, 60% in mineral oil) and, within 15 minutes, the gas evolution had ceased.. To the above reaction mixture was added a solution of methyl iodide (14.2 g, 99.8 mmol).. The reaction mixture was stirred overnight and allowed to warm to room temperature.. The reaction was triturated with hexane (3 x 150 ML) which was discarded.. The reaction mixture was poured into ice water, extracted with dichloromethane (3 x 200 ML) which was dried with anhydrous sodium sulfate.. The dry dichloromethane was concentrated to yield a solid which was triturated with a solution of ethyl acetate and hexane (1:1, 200 ML).. Compound 9 was obtained as an orange solid (16.9 g, 68.6 mmol, 72%). GC/MS, m/z = 246 at TR = 14.63 min (100%). LC/MS, [M+H]' = 247.
	With sodium hydride In water; N,N-dimethyl-formamide	32.6 Step 6: Step 6: N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide (3.77 kg) is suspended in dimethylformamide (20 L; Van Waters) and the mixture chilled in an ice bath. sodium hydride (808 g, 60% dispersion; Aldrich) is added to the suspension under a nitrogen atmosphere. The temperature of the reaction mixture is maintained below 10?C during the addition of the hydride. After the addition is complete the mixture is stirred for 1 hour, then methyl iodide (2.46 kg) is added slowly while maintaining the temperature below 10?C. The reaction mixture is stirred overnight and allowed to come to room temperature. HPLC analysis of the reaction mixture shows 97.7% product and ~2.3% of the starting material. The addition of methyl iodide (53 g; Aldrich) and continued stirring (5 hours) does not change this ratio. The reaction mixture is quenched by the addition of 1 L of water. The mixture is triturated with hexanes (2 X 4 L) which are discarded. Most of the DMF is removed under reduced pressure. The residue is diluted with water (6 L) and product is extracted with methylene chloride (20 L; Barton). The solution is dried over sodium sulfate, filtered and the solvent evaporated to give a solid. This material is triturated with hexanes (15 L) and ethyl acetate (15 L). The slurry was cooled to room temperature, filtered and washed with hexanes (0.5 L). This material is found to be only ~91% product by HPLC (area %).

	In <i>N</i>-methyl-acetamide; dichloromethane; water; ethyl acetate	32.6 Step 6 Step 6 N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide (3.77 kg) is suspended in dimethylformamide (20 L; Van Waters) and the mixture chilled in an ice bath. Sodium hydride (808 g, 60% dispersion; Aldrich) is added to the suspension under a nitrogen atmosphere. The temperature of the reaction mixture is maintained below 10?C. during the addition of the hydride. After the addition is complete the mixture is stirred for 1 hour, then methyl iodide (2.46 kg) is added slowly while maintaining the temperature below 10?C. The reaction mixture is stirred overnight and allowed to come to room temperature. HPLC analysis of the reaction mixture shows 97.7% product and ~2.3% of the starting material. The addition of methyl iodide (53 g; Aldrich) and continued stirring (5 hours) does not change this ratio. The reaction mixture is quenched by the addition of 1 L of water. The mixture is triturated with hexanes (2*4 L) which are discarded. Most of the DMF is removed under reduced pressure. The residue is diluted with water (6 L) and product is extracted with methylene chloride (20 L; Barton). The solution is dried over sodium sulfate, filtered and the solvent evaporated to give a solid. This material is triturated with hexanes (15 L) and ethyl acetate (15 L). The slurry was cooled to room temperature, filtered and washed with hexanes (0.5 L). This material is found to be only ~91% product by HPLC (area %). The material is purified by column chromatography. The material is dissolved in methylene chloride and passed through a pad of silica (~18 kg). The polarity of the eluant is gradually increased by adding ethyl acetate (Barton). Eventually the column is flushed with ethyl acetate. In this manner 2.4 kg of N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide is obtained with a purity of 98.05% by HPLC (area %).
	In <i>N</i>-methyl-acetamide	137 N-[3-[4-(Chloroacetyl)-(3-cyano-4.5-dihydropyrazolo[1,5-a]pyrimidinyl)phenyl]-N-methylacetamide EXAMPLE 137 N-[3-[4-(Chloroacetyl)-(3-cyano-4.5-dihydropyrazolo[1,5-a]pyrimidinyl)phenyl]-N-methylacetamide To 33.0 g of 3'-acetamido-3-dimethylaminoacrylophenone in 170 ml of dimethylformamide was added 6.8 g of 60% sodium hydride followed by 40 g of methyl iodide to give, after workup, 10.5 g of 3'-(N-methylacetamido)-3-(N,N-dimethylamino)acrylophenone, m.p. 129°-131° C.
	In <i>N</i>-methyl-acetamide; hexane; dichloromethane	173 N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide EXAMPLE 173 N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide A solution of 4.62 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide in 25 ml of dimethylformamide was stirred in an inert atmosphere and 1.0 g of sodium hydride (60% oil suspension) was added. After stirring for 1 hour, the liberation of hydrogen had ceased and a solution of 3.0 g of methyl iodide in 10 ml of dimethylformamide was gradually added (with cooling, if necessary). After stirring for an additional 1 hour at room temperature, any volatiles were removed at reduced pressure and then the reaction mixture was triturated 3 times with 100 ml of hexane. The reaction mixture was carefully poured into cold water and extracted exhaustively with methylene chloride. This material was evaporated at reduced pressure to yield a yellow-orange solid. A solution of the crude solid in methylene chloride was passed through a pad of hydrous magnesium silicate. Addition of hexane to the refluxing elude gave crystals which were collected after cooling. The desired compound was a yellow-orange crystalline material, mp 146°-148° C.
	In <i>N</i>-methyl-acetamide; dichloromethane; water; ethyl acetate	32.6 Step 6: Step 6: N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide (3.77 kg) is suspended in dimethylformamide (20 L; Van Waters) and the mixture chilled in an ice bath. Sodium hydride (808 g, 60% dispersion; Aldrich) is added to the suspension under a nitrogen atmosphere. The temperature of the reaction mixture is maintained below 10?C during the addition of the hydride. After the addition is complete the mixture is stirred for I hour, then methyl iodide (2.46 kg) is added slowly while maintaining the temperature below 10?C. The reaction mixture is stirred overnight and allowed to come to room temperature. HPLC analysis of the reaction mixture shows 97.7% product and ~2.3% of the starting material. The addition of methyl iodide (53 g; Aldrich) and continued stirring (5 hours) does not change this ratio. The reaction mixture is quenched by the addition of 1 L of water. The mixture is triturated with hexanes (2 X 4 L) which are discarded. Most of the DMF is removed under reduced pressure. The residue is diluted with water (6 L) and product is extracted with methylene chloride (20 L; Barton). The solution is dried over sodium sulfate, filtered and the solvent evaporated to give a solid. This material is triturated with hexanes (15 L) and ethyl acetate (15 L). The slurry was cooled to room temperature, filtered and washed with hexanes (0.5 L). This material is found to be only ~91% product by HPLC (area %). The material is purified by column chromatography. The material is dissolved in methylene chloride and passed through a pad of silica (~18 kg). The polarity of the eluant is gradually increased by adding ethyl acetate (Barton). Eventually the column is flushed with ethyl acetate. In this manner 2.4 kg of N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide is obtained with a purity of 98.05% by HPLC (area %).
	With potassium hydroxide In <i>N</i>-methyl-acetamide; dichloromethane; water	2 Preparation of N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-n-methylacetamide (Formula III) Example 2 Preparation of N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-n-methylacetamide (Formula III) To a suspension of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-acetamide (230 gm) in dimethylformamide (1150 ml) was added powdered potassium hydroxide (110.90 gm) and the reaction mixture was stirred at about 25° C.-30° C. for about 30 min. The reaction mass was cooled to about 0° C.-5° C. and methyl iodide (154.67 gm) was added in about 30 min at about the same temperature. After complete addition, the temperature was allowed to rise to about 20° C.-25° C., and while stirring, the reaction mass at about the same temperature until the reaction is completed (~3 hrs) as monitored via thin-layer chromatography (TLC). To the reaction mass was added methylene chloride (500 ml) and water (500 ml), separated the organic layer and the aqueous layer was extracted with 2500 ml methylene chloride. The combined organic layers were washed with 3500 ml water, the subsequent organic layer was dried over sodium sulfate and concentrated to dryness to give a yellow colored solid, which was triturated with n-hexane (700 ml), filtered and dried at about 50° C. until a constant weight to give a solid product (190 gm) (Purity, ~>95%, by TLC).

Reference： [1]Location in patent: experimental part Radl, Stanislav; Blahovcova, Michaela; Placek, Lukas; Pekarek, Tomas; Havlicek, Jaroslav [Journal of Heterocyclic Chemistry, 2010, vol. 47, # 2, p. 276 - 283]
[2]Current Patent Assignee: NEUROCRINE BIOSCIENCES INC - EP1214075, 2004, B1 Location in patent: Page/Page column 23; 24
[3]Current Patent Assignee: NEUROCRINE BIOSCIENCES INC - EP1352647, 2003, A1
[4]Current Patent Assignee: PFIZER INC - US6485746, 2002, B1
[5]Current Patent Assignee: PFIZER INC - US4963553, 1990, A
[6]Current Patent Assignee: PFIZER INC - US4521422, 1985, A
[7]Current Patent Assignee: NEUROCRINE BIOSCIENCES INC - EP1206248, 2003, B1
[8]Current Patent Assignee: GLENMARK PHARMACEUTICALS LTD - US2012/28045, 2012, A1

5
[ 96219-87-3 ]
[ 1227694-88-3 ]
[ 325715-02-4 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; dichloromethane; acetic acid	N-Methyl-N-[3-[3-(2-thienylcarbonyl)-pyrazolo[1.5-a]pyrimidin-7-yl]phenyl]acetamide (Compound 1) N-Methyl-N-[3-[3-(2-thienylcarbonyl)-pyrazolo[1.5-a]pyrimidin-7-yl]phenyl]acetamide (Compound 1) A mixture of (3-amino-1H-pyrazol-4-yl)-2-thienylmethanone (4) (1.93 g, 10 mmol) and N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide (6) (2.46 g, 10 mmol) in glacial acetic acid (100 mL) is refluxed for 8 hrs. Evaporation of all volatiles on a rotary evaporator gives a residue which is partitioned between aqueous saturated sodium bicarbonate and methylene chloride. The methylene chloride layer is dried over sodium sulfate and filtered. Two additional volumes of methylene chloride are added and the solution is warmed to reflux. Hexane is added until crystallization is observed. The mixture is cooled and filtered to give Compound 1 as a yellow solid (2.57 g, 7 mmol, 70%). It will be appreciated that, although specific embodiments of the invention have been described herein for purposes of illustration, various modifications may be made without departing from the spirit and scope of the invention. Accordingly, the invention is not limited except as by the appended claims.

Reference： [1]Current Patent Assignee: NEUROCRINE BIOSCIENCES INC - US6399621, 2002, B1

6
[ 1227694-86-1 ]
[ 1227694-88-3 ]

Yield	Reaction Conditions	Operation in experiment
	In <i>N</i>-methyl-acetamide; hexane; ethyl acetate; mineral oil	N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide (6) N-[3-[3-(Dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide (6) To a suspension of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-acetamide (5) (22.07 g, 95 mmol) in anhydrous dimethylformamide (114 mL) under nitrogen in an ice bath is added sodium hydride (Aldrich, 60% in mineral oil) (4.75 g, 119 mmol) and, within 15 minutes, the gas evolution has ceased. To the above reaction mixture is added a solution of methyl iodide (Aldrich) (14.2 g, 99.8 mmol). The reaction mixture is stirred overnight and allowed to warm to room temperature. The reaction is triturated with hexane (3150 mL) which is discarded. The reaction mixture is poured into ice water, extracted with dichloromethane (3200 mL) which is dried with anhydrous sodium sulfate. The dry dichloromethane is concentrated to yield a solid, which is triturated with a solution of ethyl acetate and hexane (1:1, 200 m l). Product (6) is obtained as an orange solid (16.9 g, 68.6 mmol, 72%).

Reference： [1]Current Patent Assignee: NEUROCRINE BIOSCIENCES INC - US6399621, 2002, B1

7
[ 96219-87-3 ]
[ 1227694-88-3 ]
[ 67000-01-5 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In dichloromethane	32.7 Step 7 Step 7 N-Methyl-N-[3-[3-(2-thienylcarbonyl)-pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]acetamide A fifty liter flask is charged with 1.936 kg of (3-amino-1H-pyrazol-4-yl)-2-thienylmethanone, 2.450 kg of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide and 33.3 kg of acetic acid (Van Waters). The reaction mixture is heated at reflux for 6 hours. The reaction mixture is evaporated to a residue under reduced pressure while maintaining the temperature at approximately 45?C. The residue is dissolved in methylene chloride (8 L; Spectrum) then precipitated by the addition of 32 L of methyl-t-butyl ether.

Reference： [1]Current Patent Assignee: PFIZER INC - US6485746, 2002, B1

8
[ CAS Unavailable ]
[ 16617-46-2 ]
[ 1227694-88-3 ]
[ 115932-13-3 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; acetic acid	12 N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-methylacetamide EXAMPLE 12 N-[3-(3-Cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-methylacetamide A mixture of 540 mg of 3-aminopyrazole-4-carbonitrile, 1.23 g of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide and 50 ml of glacial acetic acid was heated at reflux for 8 hours then the solvent was removed: The residue was partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic layer was separated, dried, passed through a pad of hydrous magnesium silicate and hexane was added to the refluxing filtrate to crystallize the product. The mixture was cooled and the solid collected, giving the desired product, mp 195°-197° C.

Reference： [1]Current Patent Assignee: MCCORMICK PATRICK; PFIZER INC - US4847256, 1989, A

9
[ 1227694-88-3 ]
[ 96605-70-8 ]

Yield	Reaction Conditions	Operation in experiment
		180 N-[3-(3-Benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-methylacetamide EXAMPLE 180 N-[3-(3-Benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-methylacetamide In the manner of Example 179, substituting N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide (Example 171) for N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide gave the desired product, mp 162°-164° C.

Reference： [1]Current Patent Assignee: PFIZER INC - US4521422, 1985, A

10
[ 1227694-88-3 ]
[ 96605-72-0 ]

Yield	Reaction Conditions	Operation in experiment
		183 N-[3-[3-(2-Furancarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-N-methylacetamide EXAMPLE 183 N-[3-[3-(2-Furancarbonyl)pyrazolo[1,5-a]pyrimidin-7-yl]phenyl]-N-methylacetamide In the manner of the above example, substituting N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-methylacetamide (Example 171) for N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]acetamide gave the desired product, mp 210°-212° C., which was isolated from the methylene chloride solution.

Reference： [1]Current Patent Assignee: PFIZER INC - US4521422, 1985, A

11
[ 96219-84-0 ]
[ 1227694-88-3 ]
[ 1011266-94-6 ]

Yield	Reaction Conditions	Operation in experiment
48%	With acetic acid at 65℃; for 1.5h;

Reference： [1]Hoepping, Alexander; Diekers, Michael; Deuther-Conrad, Winnie; Scheunemann, Matthias; Fischer, Steffen; Hiller, Achim; Wegner, Florian; Steinbach, Joerg; Brust, Peter [Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1184 - 1194]

12
[ 1227694-86-1 ]
[ 113469-23-1 ]
[ 74-88-4 ]
[ 1227694-88-3 ]

Yield	Reaction Conditions	Operation in experiment
	In <i>N</i>-methyl-acetamide; sodium hydride; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; mineral oil	1 Preparation of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide (Formula III) Example 1 Preparation of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-N-methylacetamide (Formula III) To a suspension of N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]-phenyl]-acetamide (50 gm) in anhydrous dimethylformamide (258 ml) under nitrogen in an ice-bath was added sodium hydride (60% suspension in mineral oil)-(10.76 gm) and within about 15 minutes, it was observed that gas formation ceased. To the above reaction mixture is added a solution of methyl iodide (32.17 gm). The reaction mixture is stirred overnight and allowed to warm to room temperature. The reaction mass is then triturated with n-hexane (3340 ml) which is discarded. The reaction mixture is then poured in ice water and extracted with methylene dichloride (345 ml). The organic layer is dried on sodium sulfate and evaporated to give a solid, which is triturated with a solution of n-hexane-ethyl acetate (1:1,453 ml) to give a solid product (22 gm) (Purity, ~90%, by thin-layer chromatography, TLC)

Reference： [1]Current Patent Assignee: GLENMARK PHARMACEUTICALS LTD - US2012/28045, 2012, A1

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1227694-88-3 ] {[proInfo.proName]}

Quality Control of [ 1227694-88-3 ]

Related Doc. of [ 1227694-88-3 ]

Product Details of [ 1227694-88-3 ]

Calculated chemistry of [ 1227694-88-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1227694-88-3 ]

Application In Synthesis of [ 1227694-88-3 ]

[ 1227694-88-3 ] Synthesis Path-Downstream 1~12

Related Functional Groups of [ 1227694-88-3 ]

Aryls

Alkenes

Amides

Ketones

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1227694-88-3 ]