[ CAS No. 1187-59-3 ] {[proInfo.proName]}

Name: 1187-59-3|N-Methylacrylamide|98% (stabilized with MEHQ)
Brand: Ambeed
SKU: A165131
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Quality Control of [ 1187-59-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1187-59-3 ]

SDS Specification

Alternatived Products of [ 1187-59-3 ]

Product Details of [ 1187-59-3 ]

CAS No. :	1187-59-3	MDL No. :	MFCD00053693
Formula :	C₄H₇NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YPHQUSNPXDGUHL-UHFFFAOYSA-N
M.W :	85.10	Pubchem ID :	14471
Synonyms :

Calculated chemistry of [ 1187-59-3 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	23.87
TPSA :	29.1 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.17
Log Po/w (XLOGP3) :	0.13
Log Po/w (WLOGP) :	-0.08
Log Po/w (MLOGP) :	-0.03
Log Po/w (SILICOS-IT) :	-0.05
Consensus Log Po/w :	0.23

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.32
Solubility :	41.0 mg/ml ; 0.481 mol/l
Class :	Very soluble
Log S (Ali) :	-0.3
Solubility :	42.9 mg/ml ; 0.504 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.61
Solubility :	21.1 mg/ml ; 0.248 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 1187-59-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1187-59-3 ]

* 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.

Upstream synthesis route of [ 1187-59-3 ]
Downstream synthetic route of [ 1187-59-3 ]

[ 1187-59-3 ] Synthesis Path-Upstream 1~10

1
[ 38188-92-0 ]
[ 1187-59-3 ]

Yield	Reaction Conditions	Operation in experiment
96%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; 10H-phenothiazine; potassium hydroxide In ethylene glycol at 180℃; Pyrolysis	(C) Into a 1000 mL four-necked flask equipped with a stirrer, a thermometer, and a gas introduction line,400 g of Meo-DEAA obtained in the step (b)6.8 g of potassium hydroxide and 0.4 g of TDA were added.Thereafter, a flask was equipped with a distillation column equipped with a packing material, a condenser and a distillation receiver, a trace nitrogen gas was flowed as a carrier,While stirring the reaction solution, the pot temperature was adjusted to 180 ° C. and the degree of vacuum was adjusted to 60 kPa,The pyrolysis reaction was carried out for 12 hours,307 g (purity = 93percent, yield = 92percent) of crude N, N-diethylacrylamide (DEAA) was obtained from a water condenser.Further, the obtained crude DEAA was transferred to a distillation purification apparatus equipped with a 20 cm McMahon packing (size 6 mm) packed tower and purified by distillation under reduced pressure (60 ° C./0.13 kPa)As a colorless liquid, 258 g of high purity product DEAA (purity 99.8percent) was obtained. Examples 2 to 18 In Example 1,The starting materials, the catalyst, the solvent, the polymerization inhibitor and the reaction conditions of each step were changed as shown in Table 1, and synthesis was carried out in the same manner as in Example 1 to obtain the respective target compound.The results are shown in Table 2.

Reference： [1] Patent: JP2015/101554, 2015, A, . Location in patent: Paragraph 0057; 0060

2
[ 50836-82-3 ]
[ 1187-59-3 ]

Reference： [1] Patent: JP2015/101552, 2015, A, . Location in patent: Paragraph 0053; 0054; 0057

3
[ 7087-68-5 ]
[ 814-68-6 ]
[ 1187-59-3 ]

Reference： [1] Patent: US5607960, 1997, A,

4
[ 5450-85-1 ]
[ 1187-59-3 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 648,650

5
[ 6830-81-5 ]
[ 1187-59-3 ]

Reference： [1] Patent: US2749355, 1952, ,
[2] Patent: US2749355, 1952, ,

6
[ 814-68-6 ]
[ 74-89-5 ]
[ 1187-59-3 ]

Reference： [1] Annales de Chimie (Cachan, France), 1894, vol. <7>2, p. 158
[2] Helvetica Chimica Acta, 1973, vol. 56, p. 1252 - 1257
[3] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1980, vol. 28, # 9-10, p. 613 - 619
[4] Patent: US2311548, 1939, ,

7
[ 57-57-8 ]
[ 74-89-5 ]
[ 1187-59-3 ]

Reference： [1] Patent: GB648886, 1947, ,

8
[ 24685-31-2 ]
[ 1187-59-3 ]

Reference： [1] Journal fuer Praktische Chemie (Leipzig), 1976, vol. 318, p. 471 - 478

9
[ 74-89-5 ]
[ 140-88-5 ]
[ 1187-59-3 ]

Reference： [1] Patent: US2683741, 1947, ,

10
[ 5450-85-1 ]
[ 1187-59-3 ]
[ 75-07-0 ]
[ 64-19-7 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 648,650

[ 1187-59-3 ] Synthesis Path-Downstream 1~79

1
[ 6830-81-5 ]
[ 1187-59-3 ]

Reference： [1]Patent: US2749355,1952,

2
[ 1809-19-4 ]
[ 1187-59-3 ]
[ 100392-14-1 ]

Reference： [1]Patent: US2754320,1948,

3
[ 57-57-8 ]
[ 74-89-5 ]
[ 1187-59-3 ]

Reference： [1]Patent: GB648886,1947,

4
[ 5450-85-1 ]
[ 1187-59-3 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 648,650

5
[ 5450-85-1 ]
[ 1187-59-3 ]
[ 75-07-0 ]
[ 64-19-7 ]

Reference： [1]Journal of the American Chemical Society,1949,vol. 71,p. 648,650

6
[ 814-68-6 ]
[ 74-89-5 ]
[ 1187-59-3 ]

Reference： [1]Annales de Chimie (Cachan, France),1894,vol. <7>2,p. 158
[2]Helvetica Chimica Acta,1973,vol. 56,p. 1252 - 1257
[3]Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques,1980,vol. 28,p. 613 - 619
[4]Patent: US2311548,1939,
[5]Angewandte Chemie - International Edition,2019,vol. 58,p. 10747 - 10751
Angew. Chem.,2019,vol. 131,p. 10858 - 10863,6

7
[ 74-89-5 ]
[ 140-88-5 ]
[ 1187-59-3 ]

Reference： [1]Patent: US2683741,1947,

8
[ 36584-97-1 ]
[ 1187-59-3 ]
[ 757-87-9 ]

Reference： [1]Journal of general chemistry of the USSR,1972,vol. 42,p. 299 - 304
Zhurnal Obshchei Khimii,1972,vol. 42,p. 308 - 314

9
[ 36584-97-1 ]
[ 1187-59-3 ]
[ 2674-96-6 ]

Reference： [1]Journal of general chemistry of the USSR,1972,vol. 42,p. 299 - 304
Zhurnal Obshchei Khimii,1972,vol. 42,p. 308 - 314

10
[ 36584-98-2 ]
[ 1187-59-3 ]
[ 24332-17-0 ]

Reference： [1]Journal of general chemistry of the USSR,1972,vol. 42,p. 299 - 304
Zhurnal Obshchei Khimii,1972,vol. 42,p. 308 - 314

11
[ 36584-98-2 ]
[ 1187-59-3 ]
[ 7162-19-8 ]

Reference： [1]Journal of general chemistry of the USSR,1972,vol. 42,p. 299 - 304
Zhurnal Obshchei Khimii,1972,vol. 42,p. 308 - 314

12
[ 1187-59-3 ]
[ 29673-64-1 ]

Reference： [1]Helvetica Chimica Acta,1973,vol. 56,p. 1252 - 1257

13
[ 1187-59-3 ]
[ 20591-34-8 ]

Reference： [1]Tetrahedron,1968,vol. 24,p. 5763 - 5768

14
[ 24685-31-2 ]
[ 1187-59-3 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1976,vol. 318,p. 471 - 478

15
[ 1187-59-3 ]
[ 507-09-5 ]
[ 66499-78-3 ]

Reference： [1]Tetrahedron,1978,vol. 34,p. 1031 - 1035

16
[ 1871-57-4 ]
[ 1187-59-3 ]
C₈H₁₄ClMgN [ No CAS ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 5929 - 5932

17
[ 1187-59-3 ]
[ 74-88-4 ]
[ 2680-03-7 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1987,vol. 60,p. 1021 - 1026

18
[ 1187-59-3 ]
[ 4083-64-1 ]
[ 207804-83-9 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 1137 - 1144

19
[ 1187-59-3 ]
N-(1,1-dimethyl-3-dimethylaminopropyl)methacrylamide [ No CAS ]
dimethyl-(2-methylcarbamoyl-ethyl)-[3-methyl-3-(2-methyl-acryloylamino)-butyl]-ammonium; chloride [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,1999,vol. 69,p. 1294 - 1298

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 41 5-Bromo-3-{N-[2-(N-methylcarbamoyl)ethyl]-2(R)-pyrrolidinylmethyl}- 1H-indole Obtained as a foam, using Preparation 7 and N-methylacrylamide. Rf 0.54 (SS 4). [alpha]D25 +66 (c=0.1, CH3 OH). Found: C,55.53; H,5.96; N,11.42. C17 H22 BrN3 O requires C,56.05; H,6.09; N,11.53%. delta(CDCl3): 1.53-1.90(4H,m), 2.16-2.30(1H,m), 2.32-2.64(5H,m), 2.74(3H,d), 3.03-3.15(1H,m), 3.17-3.30(2H,m), 7.02(1H,d), 7.16-7.31(2H,m), 7.69(1H,s), 8.08-8.30(2H,br m).

22
[ 74-89-5 ]
[ 74-86-2 ]
carbon monoxide [ No CAS ]
[ 1187-59-3 ]

Reference： [1]Patent: US2773063,1954,

23
[ 1187-59-3 ]
[ 2956-58-3 ]
[ 255375-05-4 ]
poly(N-methylacrylamide) [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 9167 - 9170

24
N-chloromethyl-N-methylacrylamide [ No CAS ]
[ 872-50-4 ]
[ 1187-59-3 ]
[ 2680-03-7 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 2328 - 2336

25
[ 1187-59-3 ]
C₁₃H₁₃ClFN₃O₄ [ No CAS ]
3-{4-[(S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-4,5-dihydro-isoxazole-5-carboxylic acid methylamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 3069 - 3072

26
[ 1187-59-3 ]
poly(N-methylacrylamide); monomer(s): N-methylacrylamide [ No CAS ]

Reference： [1]Russian Journal of Applied Chemistry,2003,vol. 76,p. 1112 - 1116

27
[ 1187-59-3 ]
[ 110853-54-8 ]
3-(4-acetylaminophenyl)-4,5-dihydroisoxazole-5-carboxylic acid methylamide [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2005,vol. 70,p. 7810 - 7815

28
[ 1187-59-3 ]
[ 75-31-0 ]
[ 1001345-72-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	In methanol; at 140℃; for 0.5h;Microwave irradiation;	General procedure: A solution of <strong>[1187-59-3]N-methylacrylamide</strong> (2) (1.88 g, 22.0 mmol) and cyclopentylamine (1.98 mL, 20.0 mmol) in MeOH (14 mL) was heated under microwave irradiation to 140 C for 30 min (Biotage Initiator). The volatiles were removed under reduced pressure, the residue diluted with MeOH (20 mL) and purified by strong cation exchange filtration (50 g SCX-2 cartridge) washing with MeOH (100 mL) and eluting with 7 M methanolic NH3 (100 mL). The eluted product was concentrated under reduced pressure to afford the title compound 3 as a brown oil (3.09 g, 18.2 mmol, 91%). This was used directly with no further purification.
94 - 100%	In methanol; at 140℃; for 0.5h;Microwave;Product distribution / selectivity;	Intermediate 19 N-Methyl-3-(propan-2-ylamino)propanamideN-Methylacrylamide (851 mg, 10.00 mmol) and isopropylamine (1.71 mL, 1.18 g, 20.00 mmol) in MeOH (10 mL) were irradiated to 140 C. for 30 mins in a microwave reaction vessel. The reaction mixture was cooled and loaded onto a SCX-2 column and washed with MeOH (100 mL). The crude product was then eluted from the SCX-2 column with NH3 (100 mL, 7M in MeOH) and the volatiles removed under reduced pressure to afford the title compound (1.56 g, Quant.) as an oil, which was used without further purification.1H NMR (400 MHz, DMSO-d6) deltaH 0.96 (d, 6H), 2.18 (t, 2H), 2.57 (d, 3H), 2.65-2.71 (m, 3H), 7.81 (br s, 1H).; Intermediate 78 N-methyl-3-(propan-2-ylamino)propanamideIsopropylamine (Aldrich; 1.5 ml, 17.62 mmol) and <strong>[1187-59-3]methyl acrylamide</strong> (ABCR; 1.0 g, 11.75 mmol) were combined in methanol (10 ml). The mixture was heated in a microwave at 140 C. for 30 min. The reaction was repeated and the combined reaction mixtures were concentrated to remove excess amine. The residue was re-dissolved in methanol and absorbed onto an SCX column (50 g), washed with methanol and eluted with ammonia/methanol. Concentration of the product containing fractions gave the title compound as a colourless oil (3.2 g, 94%).1H NMR (399.9 MHz, CDCl3) delta1.00 (6H, d), 2.27 (2H, t), 2.70-2.74 (4H, m), 2.76-2.80 (2H, m), 7.50 (1H, s)

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 5049 - 5055
[2]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 106; 116

29
[ 1187-59-3 ]
[ 75-04-7 ]
[ 1001346-08-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	In methanol; at 140℃; for 0.5h;Microwave;	<strong>[1187-59-3]N-methylacrylamide</strong> (ABCR: 851 mg, 10.00 mmol) and ethylamine (2 M in methanol, 10 mL, 20.00 mmol) were combined in a microwave reaction vessel, which was sealed and irradiated at 140 C. for 30 mins. The reaction mixture was allowed to cool and then loaded directly onto a 50 g SCX-2 cartridge, washing with methanol (100 mL) and eluting the desired product with 7 N methanolic ammonia (100 mL). Concentration under reduced pressure of product containing fractions gave the title compound as a clear oil (1.285 g; 99%)1H NMR (399.9 MHz, DMSO-d6) delta0.93-0.99 (3H, m), 2.19 (2H, t), 2.52-2.52 (2H, m), 2.54-2.59 (3H, d), 2.68 (2H, t), 7.80 (1H, br s)
99%	In methanol; at 140℃; for 0.5h;Microwave irradiation;	General procedure: A solution of <strong>[1187-59-3]N-methylacrylamide</strong> (2) (1.88 g, 22.0 mmol) and cyclopentylamine (1.98 mL, 20.0 mmol) in MeOH (14 mL) was heated under microwave irradiation to 140 C for 30 min (Biotage Initiator). The volatiles were removed under reduced pressure, the residue diluted with MeOH (20 mL) and purified by strong cation exchange filtration (50 g SCX-2 cartridge) washing with MeOH (100 mL) and eluting with 7 M methanolic NH3 (100 mL). The eluted product was concentrated under reduced pressure to afford the title compound 3 as a brown oil (3.09 g, 18.2 mmol, 91%). This was used directly with no further purification.

Reference： [1]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 117
[2]Tetrahedron Letters,2012,vol. 53,p. 5049 - 5055

30
[ 1187-59-3 ]
[ 78-81-9 ]
[ 1001346-11-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	In ethanol; at 18 - 140℃;Microwave;	<strong>[1187-59-3]N-methylacrylamide</strong> (ABCR; 1 g, 11.75 mmol) was dissolved in EtOH (5 mL). Isobutylamine (Aldrich; 2.33 mL, 23.5 mmol) was added and stirred at ambient temperature in a stoppered flask over the weekend. The reaction was then transferred to a microwave reactor vessel and heated in a microwave for 10 minutes at 140 C. Solvents were evaporated in vacuo to give the title compound as a colourless liquid. (1.78 g, 96%)1H NMR (400.132 MHz, CDCl3) delta0.93 (d, 6H), 1.74 (m, 1H), 2.35 (m, 2H), 2.43 (d, 2H), 2.78 (d, 3H), 2.85 (m, 2H), 7.88 (s, 1H)
96%	In ethanol; at 140℃; for 0.5h;Microwave irradiation;	General procedure: A solution of <strong>[1187-59-3]N-methylacrylamide</strong> (2) (1.88 g, 22.0 mmol) and cyclopentylamine (1.98 mL, 20.0 mmol) in MeOH (14 mL) was heated under microwave irradiation to 140 C for 30 min (Biotage Initiator). The volatiles were removed under reduced pressure, the residue diluted with MeOH (20 mL) and purified by strong cation exchange filtration (50 g SCX-2 cartridge) washing with MeOH (100 mL) and eluting with 7 M methanolic NH3 (100 mL). The eluted product was concentrated under reduced pressure to afford the title compound 3 as a brown oil (3.09 g, 18.2 mmol, 91%). This was used directly with no further purification.

Reference： [1]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 118
[2]Tetrahedron Letters,2012,vol. 53,p. 5049 - 5055

31
[ 33966-50-6 ]
[ 1187-59-3 ]
[ 1001346-14-0 ]

Yield	Reaction Conditions	Operation in experiment
61%	In ethanol; at 140 - 150℃; for 1.25h;Microwave;	A mixture of <strong>[1187-59-3]N-methylacrylamide</strong> (ABCR; 500 mg, 5.87 mmol), sec-butylamine (Aldrich; 530 mL, 5.22 mmol) and ethanol (4 mL) was heated in a microwave to 140 C. for 45 minutes and then at 150 C. for 30 minutes. The reaction mixture was cooled and poured onto an SCX-2 cartridge (5 g) and cartridge washed through with methanol (50 mL). Products were then eluted with 2M ammonia in methanol (50 mL) and evaporated to afford the title compound as a straw coloured oil (563 mg; 61%)1H NMR (400.132 MHz, CDCl3) delta 0.92 (t, 3H), 1.06 (d, 3H), 1.31-1.53 (m, 2H), 2.34 (m, 2H), 2.57 (m, 1H), 2.78-2.94 (m, 5H), 7.77 (s, 1H)
	In ethanol; at 140℃; for 0.5h;Microwave irradiation;	General procedure: A solution of <strong>[1187-59-3]N-methylacrylamide</strong> (2) (1.88 g, 22.0 mmol) and cyclopentylamine (1.98 mL, 20.0 mmol) in MeOH (14 mL) was heated under microwave irradiation to 140 C for 30 min (Biotage Initiator). The volatiles were removed under reduced pressure, the residue diluted with MeOH (20 mL) and purified by strong cation exchange filtration (50 g SCX-2 cartridge) washing with MeOH (100 mL) and eluting with 7 M methanolic NH3 (100 mL). The eluted product was concentrated under reduced pressure to afford the title compound 3 as a brown oil (3.09 g, 18.2 mmol, 91%). This was used directly with no further purification.

Reference： [1]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 118
[2]Tetrahedron Letters,2012,vol. 53,p. 5049 - 5055

32
[ 34967-24-3 ]
[ 1187-59-3 ]
[ 1001346-23-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	In ethanol; at 140℃; for 0.75h;Microwave;	<strong>[1187-59-3]N-methylacrylamide</strong> (ABCR; 500 mg, 5.87 mmol) and 3,5-dimethoxybenzylamine (Aldrich; 0.98 mL, 6.46 mmol) were dissolved in ethanol (4 mL) and heated in a microwave at 140 C. for 45 minutes. The mixture was poured onto a 20 g SCX-2 column, washed with methanol and eluted with 3.5N NH3 in methanol. The product fractions were evaporated to the title compound as a yellow oil (1.3 g, 88%).1H NMR (CDCl3) 2.36 (t, 2H), 2.78 (d, 3H), 2.88 (t, 2H), 3.72 (s, 2H), 3.79 (s, 6H), 6.36 (m, 1H), 6.45 (m, 2H), 7.31 (bs, 1H); MS m/z 253 [M+H]+.

Reference： [1]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 120

33
[ 1187-59-3 ]
[ 109-85-3 ]
[ 1001346-35-5 ]

Yield	Reaction Conditions	Operation in experiment
65%	In ethanol; at 140℃; for 0.666667h;Microwave;	N-Methylacrylamide (ABCR; 500 mg, 5.87 mmol), 2-Methoxyethylamine (Aldrich; 441 mg, 5.87 mmol), and EtOH (2 mL) were combined and heated in a microwave at 140 C. for 40 minutes. The reaction mixture was cooled and added to a 5 g SCX-2 column pre-wet with MeOH (2 column volumes), flushed with MeOH (2 column volumes) then the product eluted with 2M ammonia in MeOH. Product containing fractions were evaporated in vacuo to give the title compound as a clear oil (608 mg, 65%)1H NMR (399.902 MHz, CDCl3) delta2.35 (m, 2H), 2.79 (m, 5H), 2.88 (m, 2H), 3.37 (s, 3H), 3.49 (m, 2H), 7.55 (s, 1H)
65%	In ethanol; at 140℃; for 0.5h;Microwave irradiation;	General procedure: A solution of <strong>[1187-59-3]N-methylacrylamide</strong> (2) (1.88 g, 22.0 mmol) and cyclopentylamine (1.98 mL, 20.0 mmol) in MeOH (14 mL) was heated under microwave irradiation to 140 C for 30 min (Biotage Initiator). The volatiles were removed under reduced pressure, the residue diluted with MeOH (20 mL) and purified by strong cation exchange filtration (50 g SCX-2 cartridge) washing with MeOH (100 mL) and eluting with 7 M methanolic NH3 (100 mL). The eluted product was concentrated under reduced pressure to afford the title compound 3 as a brown oil (3.09 g, 18.2 mmol, 91%). This was used directly with no further purification.

Reference： [1]Patent: US2008/9482,2008,A1 .Location in patent: Page/Page column 122
[2]Tetrahedron Letters,2012,vol. 53,p. 5049 - 5055

34
[ 7087-68-5 ]
[ 814-68-6 ]
[ 1187-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	With methylamine hydrochloride; In hexane; dichloromethane;	(a) N-Methylacrylamide N,N-Diisopropylethylamine (57.8 ml, 331 mmol) was added to a stirred, ice-cooled solution of acryloyl chloride (15 g, 165.7 mmol) in anhydrous dichloromethane (200 ml) followed, portionwise, by methylamine hydrochloride (11.19 g, 165.7 mmol) so as to maintain the internal temperature of the reaction mixture below 5 C. The reaction mixture was allowed to warm to room temperature, then washed twice with water (100, then 150 ml). The combined aqueous washings were saturated with sodium chloride and exhaustively extracted with dichloromethane (*7), then the dichloromethane extracts and reaction solution were combined, dried (Na2 SO4) and evaporated under reduced pressure. The residual solid was purified by column chromatography on silica gel, eluding with a solvent gradient of ethyl acetate:hexane (0:100 to 100:0), to provide the required amide as an oil. Rf 0.10 (SS 10) delta(CDCl3): 2.88 (3H, d), 5.60 (1H, d), 5.95-6.30 (3H, m).

Reference： [1]Patent: US5607960,1997,A

35
[ 79-37-8 ]
[ 1187-59-3 ]
[ 492-38-6 ]
[ 51491-68-0 ]
4-aza-4-methyl-2-phenyl-1,6-heptadiene-3,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N-methyl-acetamide; diethyl ether; dichloromethane;	(c) 4-Aza-4-methyl-2-phenyl-1,6-heptadiene-3,5-dione A solution, prepared analogously to ld), of 2-phenylacrylyl chloride (starting from 61.9 g of 2-phenylacrylic acid, 54.3 g of oxalyl chloride and 4 ml of dimethylformamide in 350 ml of methylene chloride) is added dropwise to a stirred solution, cooled to 0-5 C., of 35.6 g of <strong>[1187-59-3]N-methylacrylamide</strong>, 89.3 g of triethylamine and 350 ml of methylene chloride. When the addition has ended, the mixture is stirred overnight at room temperature. After the reaction solution has been evaporated to about 200 ml, about 0.5 1 of diethyl ether is added, the mixture is filtered and concentrated and the residue is filtered over Hyflo-Super-Cel. After concentration, the product is obtained as a dark orange oil (which is immediately reacted further in accordance with 2b).

Reference： [1]Patent: US4883877,1989,A

36
[ 79-37-8 ]
2-(4-chlorophenyl)acryloyl chloride [ No CAS ]
[ 1187-59-3 ]
[ 51747-43-4 ]
4-aza-2-(4-chlorophenyl)-4-methyl-1,6-heptadiene3,5-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N-methyl-acetamide; dichloromethane;	(c) 4-Aza-2-(4-chlorophenyl)-4-methyl-1,6-heptadiene-3,5-dione A solution, prepared analogously to ld), of 2-(4-chlorophenyl)-acrylyl chloride (starting from 28.8 g of 2-(4-chlorophenyl)-acrylic acid, 19.9 g of oxalyl chloride and 1.5 ml of dimethylformamide in 750 ml of methylene chloride) is added dropwise to a stirred solution, cooled to 0-5 C., of 12 g of <strong>[1187-59-3]N-methylacrylamide</strong>, 31.6 g of triethylamine and 130 ml of methylene chloride. When the addition has ended, the mixture is stirred overnight at room temperature. It is worked up as in 1c) to give the title compound as a brown oil, which is immediately reacted further in accordance with 4b).

Reference： [1]Patent: US4883877,1989,A

37
[ 1187-59-3 ]
[ 127154-84-1 ]
[ 1197310-95-4 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 5446 - 5448

38
[ 785795-02-0 ]
[ 1187-59-3 ]
[ 1246361-78-3 ]

Yield	Reaction Conditions	Operation in experiment
22%	With potassium hydroxide; In 1,4-dioxane; at 0 - 20℃;	Step 1: In a 50 mL round bottom flask, tert-butyl 3-(1H-indol-2-yl)piperidine- 1-carboxylate (Int-110, 3.33 mmol, 1.0 g) was taken up with 1,4-dioxane (10 mL) then cooled in an ice/water bath. Potassium hydroxide (3.33 mmol, 0.187 g) was next added followed by <strong>[1187-59-3]N-<strong>[1187-59-3]methyl acrylamide</strong></strong> (4.99 mmol, 0.425 g). The ice/water bath was removed and the reaction was allowed to warm to ambient temperature overnight. The reaction mixture was poured into H2O (150 mL), extracted with EtOAc (4 x 75 mL). The organic layers were combined and washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo and purified by flash chromatography (40-70% EtOAc/Hexanes) to afford 0.278 g of tert-butyl 3-(l-(3-(methylamino)-3-oxopropyl)-1H- indol-2-yl)piperidine-1-carboxylate (InM 11), 22% yield. ESI-MS: m/z 286.4 = (M+H)+

Reference： [1]Patent: WO2010/111634,2010,A2 .Location in patent: Page/Page column 197

39
[ 1187-59-3 ]
[ 1255641-10-1 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; acetic acid; sodium nitrite; at 0 - 15℃; for 15.5h;	EXAMPLE 6; A solution of the amide (0.10 mole):in a mixture of acetic acid (10 ml) and acetic anhydride (50 ml) is cooled to 00C and 15 grams of granular sodium nitrite (0.22 moles) is added over 5 hours. After 10 hours at 0 0C the temperature is allowed to rise to 10-15 0C for 30 minutes and the mixture is poured into a mixture of ice and water. [Theta0128] The nitrosoamide:is extracted with ether, and the upper phase is washed with water, with an aqueous solution of sodium carbonate (5%), with water, and then dried with anhydrous sodium sulfate. The solvent is removed (under vacuum), and depending on the properties of the nitrosoamide, the product is either distilled under vacuum in a temperature less than 40 0C, or recrystallized from ether- pentane mixtures.

Reference： [1]Patent: WO2010/132509,2010,A2 .Location in patent: Page/Page column 40

40
[ 1187-59-3 ]
[ 1258440-18-4 ]
[ 1258852-55-9 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 80℃; for 1h;	2-[(1-Methylethyl)oxy]-5-[5-(1 ,2,3,4-tetrahydro-5-isoquinolinyl)-1 ,3,4-thiadiazol-2- yl]benzonitrile hydrochloride (Preparation 56) (40mg), <strong>[1187-59-3]N-methyl-2-propenamide</strong> (12mg) and DBU (0.044 ml, 0.29 mmol) were dissolved in acetonitrile (1 ml) and heated to 800C for 1 h. The acetonitrile (1 ml) was removed under vacuum. Water (10ml) was added and the mixture extracted using diethyl ether (2x 15ml). The organic phase was dried (Na2SO4) and the solvent removed under vacuum to give a crude product. The product was purified using flash chromatography (methanol / DCM, 0-10%) to give 3-[5-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1 ,3,4-thiadiazol- 2-yl)-3,4-dihydro-2(1 /-/)-isoquinolinyl]-Lambda/-methylpropanamide as a yellow solid (27mg). LCMS (Method formate): Retention time 0.87min, MH+ = 462

Reference： [1]Patent: WO2010/146105,2010,A1 .Location in patent: Page/Page column 236-237

41
[ 1187-59-3 ]
[ 1341216-05-4 ]
[ 1342826-49-6 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; acetonitrile;	Example 59 3-(4-((6-(7-(4-(3-cyclopropylureido)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)piperazin-1-yl)-N-methylpropanamide (81) A stirred suspension of compound 49 (100 mg, 0.19 mmol, scheme 15) and <strong>[1187-59-3]N-methylacrylamide</strong> (1.5 mL) in acetonitrile (20 mL) was heated to 110 C. overnight in a sealed flask. The reaction mixture was cooled to RT, concentrated, and the residue was purified twice by Biotage (SNAP 25 g cartridge; 2% of ammonium hydroxide in MeOH/DCM: 5/95 to 15/85 over 20 CV and SiliaFlash 12 g cartridge; 2% of ammonium hydroxide in MeOH/DCM: 5/95 to 15/85 over 20 CV, then 15/85 over 5 CV), to afford the title compound 81 (50 mg, 0.08 mmol, 43% yield) as a white sticky solid. 1H NMR (400 MHz, DMSO-d6) delta (ppm): 8.72 (s, 1H), 8.54 (bd, J=1.4 Hz, 1H), 8.52 (d, J=5.5 Hz, 1H), 8.33 (s, 1H), 8.24 (d, J=8.0 Hz, 1H), 7.85 (dd, J=8.1, 2.1 Hz, 1H), 7.85-7.77 (m, 1H), 7.73 (dd, J=13.6, 2.4 Hz, 1H), 7.38 (t, J=9.1 Hz, 1H), 7.20 (bd, J=8.9 Hz, 1H), 6.64 (bd, J=5.4 Hz, 1H), 6.57 (bd, J=2.5 Hz, 1H), 3.54 (s, 2H), 2.59-2.51 (m, 6H), 2.47-2.11 (m, 10H), 0.72-0.58 (m, 2H), 0.50-0.36 (m, 2H). MS 604.4 (m/z): (M+H).

Reference： [1]Patent: US2011/257100,2011,A1

42
[ 38041-19-9 ]
[ 1187-59-3 ]
[ 1001345-74-9 ]