[ CAS No. 15430-52-1 ] {[proInfo.proName]}

Name: 15430-52-1|Prop-2-yn-1-amine hydrochloride|95%
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SKU: A458666
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Quality Control of [ 15430-52-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 15430-52-1 ]

SDS Specification

Alternatived Products of [ 15430-52-1 ]

Product Details of [ 15430-52-1 ]

CAS No. :	15430-52-1	MDL No. :	MFCD00012907
Formula :	C₃H₆ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IKXNIQJDNKPPCH-UHFFFAOYSA-N
M.W :	91.54	Pubchem ID :	11205720
Synonyms :

Calculated chemistry of [ 15430-52-1 ]

Physicochemical Properties

Num. heavy atoms :	5
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.33
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	24.37
TPSA :	26.02 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) :	-6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.37
Log Po/w (WLOGP) :	0.46
Log Po/w (MLOGP) :	0.6
Log Po/w (SILICOS-IT) :	-0.37
Consensus Log Po/w :	0.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.64
Solubility :	20.9 mg/ml ; 0.229 mol/l
Class :	Very soluble
Log S (Ali) :	-0.48
Solubility :	30.2 mg/ml ; 0.33 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.18
Solubility :	140.0 mg/ml ; 1.52 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.17

Safety of [ 15430-52-1 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P301+P310-P305+P351+P338	UN#:	2811
Hazard Statements:	H301-H315-H319-H335	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 15430-52-1 ]

* 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.

Upstream synthesis route of [ 15430-52-1 ]
Downstream synthetic route of [ 15430-52-1 ]

[ 15430-52-1 ] Synthesis Path-Upstream 1~2

1
[ 590-28-3 ]
[ 15430-52-1 ]
[ 5221-62-5 ]

Reference： [1] Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1966, vol. 299, # 2, p. 107 - 112

2
[ 24424-99-5 ]
[ 15430-52-1 ]
[ 92136-39-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine In dichloromethane for 2 h; Cooling with ice	Propargylamine hydrochloride (3.6 g, 39 mmol) and triethylamine (11.5 mL, 83 mmol, 2.13 equiv) were dissolved in CH₂Cl₂(100 mL) and this solution was cooled on ice. Then, a solution of Boc₂O (8.5 g, 40 mmol), (1.03 equiv) in CH₂Cl₂ (50 mL) was added dropwise and the obtained reaction mixture was stirred for 2 h. After removing the solvent under reduced pressure, the residue was redissolved in EtOAc (150 mL) and this solution was washed with 1 N KHSO₄ (3 x 75 mL) and brine (150 mL). The EtOAc solution was dried (Na₂SO₄) and concentrated in vacuo to give 8 as pink crystals in 96percent yield (5.8 g). Rf 0.70 (CH₂Cl₂/MeOH 95:5); ¹H NMR (300 MHz, CDCl₃, 25 °C): d 4.71 (broad s, 1H; urethane NH), 3.93(m, 2H; CH2), 2.22 (s, 1H; ^CH), 1.46 (s, 9H; C(CH3)3); ¹³C NMR(75.5 MHz, CDCl₃, 25 °C): d 155.3, 80.0, 69.3, 30.4, 28.3, 27.4.

Reference： [1] European Journal of Medicinal Chemistry, 2014, vol. 88, p. 55 - 65
[2] Organic Letters, 2014, vol. 16, # 12, p. 3196 - 3199

[ 15430-52-1 ] Synthesis Path-Downstream 1~88

1
[ 112-29-8 ]
[ 15430-52-1 ]
[ 100539-11-5 ]

Reference： [1]Annales de Chimie (Cachan, France),1958,vol. <13>3,p. 656,676
Bulletin de la Societe Chimique de France,1958,p. 490,492

2
[ 590-28-3 ]
[ 15430-52-1 ]
[ 5221-62-5 ]

Reference： [1]Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft,1966,vol. 299,p. 107 - 112

3
[ 15430-52-1 ]
[ 1069-72-3 ]
[ 38018-22-3 ]

Reference： [1]Journal of medicinal chemistry,1970,vol. 13,p. 651 - 657

4
[ 15430-52-1 ]
[ 98-88-4 ]
[ 1464-98-8 ]

Reference： [1]Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft,1966,vol. 299,p. 107 - 112
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 3389 - 3395
[3]Angewandte Chemie - International Edition,2013,vol. 52,p. 12409 - 12413
Angew. Chem.,2013,vol. 125,p. 12635 - 12639,5

5
[ 75-15-0 ]
[ 15430-52-1 ]
[ 52829-72-8 ]

Reference： [1]Liebigs Annalen der Chemie,1985,p. 58 - 64

6
[ 50-00-0 ]
[ 544-92-3 ]
[ 15430-52-1 ]
[ 56096-28-7 ]

Reference： [1]Tetrahedron,1988,vol. 44,p. 4431 - 4446

7
[ 6972-27-6 ]
[ 15430-52-1 ]
[ 94154-88-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1987,vol. 52,p. 2730 - 2734

8
[ 4676-39-5 ]
[ 15430-52-1 ]
N-Propargyl-3,4-methylendioxyphenylisopropylamin [ No CAS ]

Reference： [1]Journal of Pharmaceutical Sciences,1980,vol. 69,p. 192 - 195

9
[ 71107-31-8 ]
[ 15430-52-1 ]
[ 80672-64-6 ]
[ 80672-63-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1981,vol. 16,p. 529 - 532
[2]European Journal of Medicinal Chemistry,1981,vol. 16,p. 529 - 532

10
[ 74213-24-4 ]
[ 15430-52-1 ]
[ 2763-93-1 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 3113 - 3116

11
[ 15430-52-1 ]
[ 75292-88-5 ]
[ 75293-09-3 ]

Reference： [1]European Journal of Medicinal Chemistry,1983,vol. 18,p. 353 - 358

12
[ 15430-52-1 ]
[ 133605-38-6 ]
[ 133605-37-5 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 3707 - 3711
[2]Journal of Organic Chemistry,1991,vol. 56,p. 3707 - 3711

13
[ 15430-52-1 ]
[ 108-24-7 ]
[ 65881-41-6 ]

Reference： [1]Synthesis,1991,p. 547 - 560

14
[ 146039-12-5 ]
[ 15430-52-1 ]

Reference： [1]Synthesis,1985,p. 202 - 204

15
[ 85231-95-4 ]
[ 15430-52-1 ]

Reference： [1]Synthesis,1982,p. 922 - 924

16
[ 15430-52-1 ]
[ 15486-96-1 ]
[ 79570-96-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1981,vol. 16,p. 379 - 381

17
[ 32710-65-9 ]
[ 15430-52-1 ]
[ 192802-88-3 ]

Reference： [1]Journal of Heterocyclic Chemistry,2001,vol. 38,p. 645 - 648

18
[ 27317-69-7 ]
[ 15430-52-1 ]
[ 828927-37-3 ]

Reference： [1]Journal of Organometallic Chemistry,2004,vol. 689,p. 4837 - 4847

19
[ 15430-52-1 ]
[ 1204-28-0 ]
[ 782450-39-9 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 8645 - 8657

20
[ 7535-56-0 ]
[ 15430-52-1 ]
[ 461638-99-3 ]

Reference： [1]Organic Letters,2002,vol. 4,p. 2917 - 2920

21
[ 362-03-8 ]
[ 15430-52-1 ]
[ 309924-32-1 ]

Reference： [1]Organic letters,2000,vol. 2,p. 3413 - 3416

22
[ 15430-52-1 ]
disodium (3-aminopropyl)-1,1-bis-H-phosphinate hydrochloride [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 5909 - 5912

23
[ 13734-41-3 ]
[ 35661-60-0 ]
[ 15430-52-1 ]
[ 80354-38-7 ]
C₃₄H₅₈N₁₂O₁₁ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 4574 - 4577

24
[ 62147-49-3 ]
[ 333-20-0 ]
[ 15430-52-1 ]
[ 497856-22-1 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of potassium thiocyanate (31.1 g), dihydroxyacetone dimer (19.2 g) and (2-propyn-1-yl)amine hydrochloride (25.0 g) was added by portionsportions to a mixed solution of acetic acid (23 ml) and 1-butanol (155 ml). The mixture was stirred for 10 days at room temperature, water (30 ml) was added to the mixture, and the mixture was stirred for 30 minutes. The precipitated solid was collected by filtration, and further washed with water (45 ml) twice and diisopropyl ether once. The obtained solid was dried under reduced pressure, to give 5-hydroxymethyl-2-mercapto-1-(2-propyn-1-yl)imidazole (28.9 g) as colorless crystals. 1H-NMR (200 MHz, DMSO-d6) delta 3.31 (1H, t, J = 2.6 Hz), 4.42 (2H, d, J = 5.2 Hz), 4.90 (2H, d, J = 2.6 Hz), 5.37 (1H, t, J = 5.2 Hz), 6.85 (1H, s), 12.18 (1H, br)

Reference： [1]Patent: EP1422228,2004,A1 .Location in patent: Page 244

26
C₁₆H₁₉NO₂S [ No CAS ]
[ 15430-52-1 ]
C₁₈H₂₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With sodium acetate; In ethanol; at 110℃; for 16h;	Step 2; A mixture of the product of Step 1 (38 mg, 0.13 mmol), sodium acetate (11 mg, 0.14 mmol), and <strong>[15430-52-1]propargylamine hydrochloride</strong> (13 mg, 0.14 mmol) in ethanol (1 mL) in a sealed reaction vessel was heated with stirring at 110 C for 16 h. The reaction mixture was filtered through a 0. 45 mum syringe-tip filter (PTFE) and purified by reverse phase preparative HPLC to give the product as an oil (12 mg, 31%).

Reference： [1]Patent: WO2005/73221,2005,A1 .Location in patent: Page/Page column 74

27
[ 19241-36-2 ]
[ 15430-52-1 ]
[ 548797-03-1 ]
[ 548796-98-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; water; ethyl acetate;	EXAMPLE 9 1-(5-Chloro-2-methylphenyl)-3-(2-propynyl)-2-thioxo-4,5-imidazolidinedione 5-Chloro-2-methylphenyl isothiocyanate (18.3 g; 0.1 mol) was added dropwise to the mixture of 2-propynylamine hydrochloride (9.2 g, 0.1 mol) and triethyl amine (20 mL) in methylene chloride (200 mL). The mixture was stirred for 18 hours at ambient temperature. The mixture was evaporated to dryness. The residue was stirred in water (200 mL) for 1 hour then filtered. The solid was dissolved in ethyl acetate (300 mL) and washed with 1 N hydrochloric acid (2*200 mL) then with water (300 mL). The organic phase was dried over anhydrous magnesium sulfate and evaporated to dryness to give 16.8 g of N-(5-chloro-2-methylphenyl)-N'-(2-propynyl)thiourea.

Reference： [1]Patent: US2003/119889,2003,A1

Yield	Reaction Conditions	Operation in experiment
		And 36% hydrochloric acid (20.7 g, 0.2 mol) was added dropwise at 60 C. over one hour, followed by stirring at 60 C. for 1.5 hours. Then, 3.5 g of water was added and the mixed solution was separated to obtain the aqueous phase and organic phase. The organic phase was extracted once with 5 g of water and the resulting aqueous phase was combined with the above aqueous phase. To the mixture, 64 g of 2-propanol was added at 60 C. and after cooling to 5 C., the deposited crystal was obtained by filtration. This crystal was washed with 20 g of 2-propanol three times and dried to obtain propargylamine hydrochloride (10.1 g, purity: 100%, yield: 65%).
		Example 2 Propargyl methanesulfonate (31.6 g, 0.236 mol) and benzaldehyde (31.9 g, 0.3 mol) were dissolved in 103 g of toluene and an aqueous 28% ammonia solution (122 g, 2 mol) was added dropwise at 21 C. over 8 hours to the solution, followed by stirring at the same temperature for 15 hours. After separating, the resultant organic phase was washed with water and concentrated until the weight became 57.3 g to obtain a toluene solution containing 28.6 g (yield: 85%) of N-benzylidene-2-propynylamine. To the resulting solution, 36% hydrochloric acid (30.4 g, 0.3 mol) was added dropwise at 20 C. over one hour, followed by stirring at 20 C. for 2 hours. Then, 2.5 g of water was added and the mixed solution was separated at 60 C. to obtain the aqueous phase and organic phase. The organic phase was extracted once with 5 g of water and the resulting aqueous phase was combined with the above aqueous phase. After 42.4 g of toluene was added, the mixture was heated to 62 C. and dehydrated by azeotropic distillation under 120 mmHg. Thus 10.6 g of water was distilled off. After returning to an atmospheric pressure, 18.8 g of 2-propanol was added to the mixture at 60 C. After cooling, the deposited crystal was obtained by filtration. This crystal was washed twice with 15 g of 2-propanol and dried to obtain propargylamine hydrochloride (18.1 g, purity: 86%, yield: 85%).
		Example 3 An aqueous 28% ammonia solution (166.4 g, 2.74 mol) and benzaldehyde (30.6 g, 0.288 mol) were mixed and a solution prepared by dissolving propargyl methanesulfonate (36.7 g, 0.274 mol) in 147 g of toluene was added dropwise at 20-25 C. over 3 hours to the solution, followed by stirring at the same temperature for 3 hours. After separating, the organic phase and aqueous phase were obtained. The organic phase obtained by washing the aqueous phase twice with 25 g of toluene was combined with the above organic phase and concentrated until the weight became 78 g to obtain a toluene solution of N-benzylidene-2-propynylamine. To this solution, 36% hydrochloric acid (41.7 g, 0.411 mol) was added dropwise at 20-25 C. over 10 minutes, followed by stirring at 20-25 C. for 2.5 hours. Fifty grams of ethanol was added and, after cooling to 5 C., the deposited crystal was obtained by filtration and the filtrate was simultaneously obtained. This crystal was washed once with 25 g of ethanol and dried to obtain 13.7 g of propargylamine hydrochloride. The filtrate and wash ethanol after the crystal was obtained by filtration were combined and, after separating, the resulting lower layer was concentrated until the weight became 82 g. After cooling to 5 C., the deposited crystal was obtained by filtration. This crystal was washed once with 6.2 g of ethanol and dried to obtain 3.2 g of propargylamine hydrochloride.

		To this crude product, 5 ml of ethanol and 36% hydrochloric acid (3.0 g, 30 mmol) were added, followed by stirring at 20 C. for 5 hours. After cooling to 5 C., the deposited crystal was obtained by filtration and the filtrate was simultaneously obtained. The obtained crystal was washed with ethanol and dried to obtain 878 mg of propargylamine hydrochloride. The filtrate was concentrated and recrystallized from ethanol to obtain 546 mg of propargylamine hydrochloride.
		Example 5 According to the same manner as that described in Example 4 except for using p-methoxybenzaldehyde (3.54 g, 26 mmol) in place of o-chlorobenzaldehyde, the operation was conducted to obtain propargylamine hydrochloride (1.32 g, purity: 87%, yield: 63%).
		Example 6 According to the same manner as that described in Example 4 except for using benzaldehyde (2.76 g, 26 mmol) in place of o-chlorobenzaldehyde, propargyl benzenesulfonate (3.92 g, 20 mmol) in place of propargyl methanesulfonate and 19.6 g of toluene in place of 10.7 g of toluene, the operation was conducted to obtain propargylamine hydrochloride (1.40 g, purity: 99%, yield: 77%).
		Then, 2.5 g of water was added and the mixed solution was separated at 60 C. to obtain the aqueous phase and organic phase. The aqueous phase obtained by extracting organic phase (24.9 g) once with 4 g of water was combined with the above aqueous phase. To this aqueous phase (18.2 g) was added 18.2 g of toluene and, after the mixture was heated to 62 C. and dehydrated by azeotropic distillation under 90 mmHg, 10 g of water was distilled off. After returning to an atmospheric pressure, 10 g of 2-propanol was added to the mixture at 60 C. After cooling to 5 C., the deposited crystal was obtained by filtration. This crystal was washed twice with 5 g of 2-propanol and dried to obtain propargylamine hydrochloride (5.93 g, purity: 100%, yield: 94%).

29
[ 106-96-7 ]
[ 15430-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ammonia; benzaldehyde; In toluene;	Example 7 An aqueous 28% ammonia solution (12.1 g, 200 mmol) and benzaldehyde (2.23 g, 21 mmol) were mixed and a solution prepared by dissolving propargyl bromide (2.38 g, 20 mmol) in 9.5 g of toluene was added dropwise at 20 C. over 0.7 hour to the solution, followed by stirring at the same temperature for 10 hours. After separating, the resulting organic phase was concentrated until the weight became to 10 g to obtain a toluene solution containing N-benzylidene-2-propynylamine. To this solution, 36% hydrochloric acid (3.0 g, 30 mmol) was added, followed by stirring at 20 C. for 5 hours. Then, the toluene phase was removed by decantation. After cooling to 5 C., the deposited crystal was obtained by filtration and the filtrate was simultaneously obtained. The resulting crystal was washed with ethanol and dried to obtain 889 mg of propargylamine hydrochloride. The filtrate was concentrated and recrystallized from ethanol to obtain 271 mg of propargylamine hydrochloride. The resulting propargylamine hydrochlorides were combined (weight: 1.16 g). As a result, the purity was 99% and the yield to the raw material (propargyl methanesulfonate) was 63%.

Reference： [1]Patent: US5756769,1998,A

30
[ 624-65-7 ]
[ 15430-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	In toluene;	Example 8 According to the same manner as that described in Example 7 except for using propargyl chloride (1.49 g, 20 mmol) in place of propargyl bromide and 6.0 g of toluene in place of 9.5 g of toluene, the operation was conducted to obtain propargylamine hydrochloride (790 mg, purity: 96%, yield: 42%).

Reference： [1]Patent: US5756769,1998,A

31
aqueous propargylamine [ No CAS ]
2-benzoyl-benzo[b]thiophen-3-ol, phosphorus(V) chloride [ No CAS ]
[ 15430-52-1 ]
(E)-2-[(2-propynyl)amino]phenylmethylene}-benzo[b]thiophen-3-(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium carbonate; In water;	EXAMPLE 29 (E)-2-[(2-propynyl)amino]phenylmethylene}-benzo[b]thiophen-3-(2H)-one Prepared as in Example 1 from 2-benzoyl-benzo[b]thiophen-3-ol, phosphorus(V) chloride and an aqueous propargylamine solution obtained by reacting a solution of 10 gm of <strong>[15430-52-1]propargylamine hydrochloride</strong> in 10 cc of water with a solution of 10.6 gm of anhydrous sodium carbonate in 20 cc of water, with a yield of 46% of theory. M.p. 126-128 C. (ethyl acetate/petroleum ether 1:1). C18 H13 NOS (291.37): Calc.: C-74.20%; H-4.50%; N-4.81%; S-11.00%; Found: C-74.04%; H-4.47%; N-4.70%; S-11.05%. p IR(CH2 Cl2): --C=C--H 3300, C=O approx. 1600 cm-1; also associated H; UV (ethanol): lambda max (neutral) 266-276 (E=0.45); 286 (E=0.48); 319 (E=0.56); 434 (E=0.54); lambda max (alkaline) 255 (E=0.70); 313 (E=0.34); 434 (E=0.22). (Concentration: 50 mug/ml: layer thickness 0.2 cm). 1 H-NMR(CDCl3, 80 MHz): delta 11.75 (1H, broad, internal H bridge); 7.95 (1H-dd, J=7 Hz and 2 Hz; ar. H); 7.7-7.1 (8H-m; ar. H); 3.94 (2H-dd, J=6 Hz and 2.5 Hz; --CH2 --); 2.32 (1H-t; J=2.5 Hz).

Reference： [1]Patent: US4288437,1981,A

32
2-guanidino-4-[3-(3-cyano-2-methylisothioureido)phenyl]thiazole [ No CAS ]
[ 15430-52-1 ]
2-guanidino-4-[3-(2-cyano-3-propargylguanidino)phenyl]thiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In methanol;	EXAMPLE 33 A mixture of 2-guanidino-4-[3-(3-cyano2-methylisothioureido)phenyl]thiazole (0.5 g.), <strong>[15430-52-1]propargylamine hydrochloride</strong> (1.45 g.) and triethylamine (3 ml.) was stirred overnight in methanol (5 ml.). The mixture was then evaporated to dryness and the residue triturated successively with water, ethyl acetate and acetonitrile to give a solid. This was filtered off and air-dried to give 0.075 g. of 2-guanidino-4-[3-(2-cyano3-propargylguanidino)phenyl]thiazole, m.p.>300 C.

Reference： [1]Patent: US4315009,1982,A

33
[ 32315-10-9 ]
[ 15430-52-1 ]
[ 286371-71-9 ]
[ 286370-21-6 ]

Yield	Reaction Conditions	Operation in experiment
41%	With triethylamine; In methanol; chloroform;	Example 69 N-{4-[(6,7-Dimethoxy-4-quinazolinyl)-oxy]phenyl}-N'-(2-propynyl)urea 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.2 ml), and a solution of triphosgene (50 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, <strong>[15430-52-1]propargylamine hydrochloride</strong> (31 mg) was added to the reaction solution, and the mixture was stirred at room temperature overnight. Methanol was added to the reaction solution, and the mixture was purified by HPLC by development with chloroform/methanol to give 26 mg (yield 41%) of the title compound. 1H-NMR (DMSO-d6, 400 MHz): delta 3.11 - 3.12 (m, 1H), 3.89 - 3.90 (m, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 6.49 (t, J = 5.9 Hz, 1H), 7.17 (d, J = 9.0 Hz, 2H), 7.38 (s, 1H), 7.48 (d, J = 8.8 Hz, 2H), 7.55 (s, 1H), 8.53 (s, 1H), 8.68 (s, 1H) Mass analysis, found (ESI-MS, m/z): 379 (M++1)

Reference： [1]Patent: EP1153920,2001,A1

34
[ 286371-63-9 ]
[ 32315-10-9 ]
[ 15430-52-1 ]
[ 286370-32-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine; In chloroform;	Example 81 N-{2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-(2-propynyl)urea 2-Chloro-4-[(6,7-dimethoxy-4-quinazolinyl)oxy]-aniline (50 mg) was dissolved in chloroform (5 ml) and triethylamine (1 ml), and a solution of triphosgene (45 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, <strong>[15430-52-1]propargylamine hydrochloride</strong> (21 mg) was added to the reaction solution, and the mixture was stirred at room temperature for additional 30 min. The precipitated crystal was collected by filtration and was washed togive 38 mg (yield 61%) of the title compound. 1H-NMR (DMSO-d6, 400 MHz): delta 3.16 - 3.17 (m, 1H), 3.93 - 3.95 (m, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 7.25 (dd, J = 2.7 Hz, 9.0 Hz, 1H), 7.30 (t, J = 5.6 Hz, 1H), 7.39 (s, 1H), 7.50 (d, J = 2.7 Hz, 1H), 7.55 (s, 1H), 8.16 (d, J = 9.3 Hz, 1H), 8.18 (s, 1H), 8.56 (s, 1H) Mass analysis, found (ESI-MS, m/z): 413 (M++1)

Reference： [1]Patent: EP1153920,2001,A1

35
[ 286371-72-0 ]
[ 32315-10-9 ]
[ 15430-52-1 ]
[ 144-55-8 ]
[ 286370-43-2 ]

Yield	Reaction Conditions	Operation in experiment
33%	With triethylamine; In chloroform;	Example 92 N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluorophenyl}-N'-(2-propynyl)urea 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-2-fluoroaniline (50 mg) was dissolved in chloroform (3 ml) and triethylamine (0.3 ml), and a solution of triphosgene(47 mg) in chloroform was then added to the solution. The mixture was stirred at room temperature for 30 min. Next, <strong>[15430-52-1]propargylamine hydrochloride</strong> (29 mg) was added to the reaction solution, and the mixture was further stirred at room temperature overnight. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was washed with chloroform to give 21 mg (yield 33%) of the title compound. 1H-NMR (DMSO-d6, 400 MHz): delta 3.15 (t, J = 2.4 Hz, 1H), 3.91 - 3.94 (m, 2H), 3.97 (s, 3H), 3.99 (s, 3H), 7.07 - 7.11 (m, 1H), 7.33 (dd, J = 2.4 Hz, 11.7 Hz, 1H), 7.39 (s, 1H), 7.54 (s, 1H), 8.09 - 8.15 (m, 1H), 8.47-8.48 (m, 1H), 8.56 (s, 1H) Mass analysis, found (ESI-MS, m/z): 397 (M++1)

Reference： [1]Patent: EP1153920,2001,A1

36
[ 24424-99-5 ]
[ 15430-52-1 ]
1-(N-tert-butyloxycarbonylamino)-prop-2-yne hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95.2%	With triethylamine; In tetrahydrofuran; water; at 20℃; for 0.75h;	Example 1 Synthesis of mesylate salt of 5-(2-dimethylaminoethoxy)-1H-indole-2-carboxylic acid [3-(4-hydroxycarbamoylphenyl)prop-2-ynyl]amide Step 1 To a suspension of <strong>[15430-52-1]propargylamine hydrochloride</strong> (25 g, 273.1 mmol) in anhydrous THF (250 mL) were added in sequence Et3N (38.06 mL, 273.1 mmol), di-tert-butyl dicarbonate (59.6 g, 273.1 mmol), and Et3N (38.06 mL, 273.1 mmol). After stirring at room temperature for 15 min, additional Et3N (19.03 mL, 136.6 mmol) and water (~20 mL) were added and gas evolution was monitored. After stirring for 30 min, no further gas evolution was observed and TLC [EtOAc/hexane, (1:2)] showed complete consumption of <strong>[15430-52-1]propargylamine hydrochloride</strong>. The reaction was quenched with 0.25M aqueous HCl (~300 mL) until the solution became clear and diluted with EtOAc (250 mL). The organic phase was separated and washed with 0.5M aqueous HCl, brine, then dried over sodium sulfate. Concentration in vacuo provided crude 1-N-(tert-butyloxycarbonylamino)-2-propyne (40.35 g, 95.2%) which became a white solid after drying under high vacuum overnight.

Reference： [1]Patent: US2007/105939,2007,A1 .Location in patent: Page/Page column 7-8

37
(trans-4-[2-(3-bromo-2-methyl-benzylamino)-5-nitro-pyrimidin-4-ylamino]-methyl}-cyclohexyl)-methanol [ No CAS ]
[ 15430-52-1 ]
[trans-4-({2-[3-(3-amino-prop-1-ynyl)-2-methyl-benzylamino]-5-nitro-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.4%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 80℃;	Example 10. Synthesis of [*r°ns-4-({2-[3-(3-amino-prop-l-ynyl)-2-methyl- benzylamino]-5-nitro-pyrimidin-4-ylamino}-methyl)-cycIohexyl] -methanol; To a solution of (^ralphar°-4-[2-(3-bromo-2-methyl-benzylamino)-5-nitro-pyrimidin-4- ylamino] -methyl} -cyclohexyO-methanol (100 mg, 0.215 mmol) and prop-2-ynylamine hydrochloride (39.4 mg, 0.431 mmol) in triethylamine (300 muL, 2.15 mmol) and N, N- dimethylformamide (1.0 mL) was added copper (I) iodide (6.8 mg, 0.022 mmol) and bis(triphenylphosphine)palladium(II) chloride (9.7 mg, 0.013 mmol), and the solution was heated at 80 0C overnight. The solution was diluted with saturated NaHCO3 and extracted with dichloromethane. The combined organics were dried over Na2SO4 and concentrated. The material was purified via silica gel chromatography using from 0-10% methanol in dichloromethane to afford 2.3 mg (2.4%) of [4-({2-[3-(3-amino-prop-l-ynyl)-2-methyl- benzylarnino]-5-nitro-pyrimidin-4-ylarnino}-methyl)-cyclohexyl]-inethanol, m/z 439.5 (M + H)+.

Reference： [1]Patent: WO2007/76247,2007,A1 .Location in patent: Page/Page column 37-38

38
3,5-bis-{8-(1H-1,2,3-triazol-4-yl)-(3,6-dioxa)octyl-[2,4,6-tri-O-acetyl-3-O-4-methylbenzophenon-β-D-galactopyranosyl-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside]methoxy}benzoic acid [ No CAS ]
[ 15430-52-1 ]
C₁₀₄H₁₂₃N₇O₄₃ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2006,vol. 4,p. 4387 - 4394

39
[ 50371-52-3 ]
[ 15430-52-1 ]
[ 1006055-08-8 ]

Reference： [1]Synthesis,2007,p. 3620 - 3626

40
aqueous cadmium chloride [ No CAS ]
[ 15430-52-1 ]
2HC₂CH₂NH₃⁽¹⁺⁾*CdCl₄^(2-)={HC₂CH₂NH₃}2CdCl₄ [ No CAS ]

Reference： [1]Journal of Physics and Chemistry of Solids,1993,vol. 54,p. 349 - 356

41
potassium nickel arsenate [ No CAS ]
[ 15430-52-1 ]
0.16C₃H₃NH₃⁽¹⁺⁾*0.84K⁽¹⁺⁾*Ni⁽²⁺⁾*AsO₄^(3-)=(CH(C)CH₂NH₃)016K_0.84NiAsO₄ [ No CAS ]

Reference： [1]Journal of Solid State Chemistry,1987,vol. 69,p. 240 - 251

42
[ 1271-42-7 ]
[ 15430-52-1 ]
ferrocenoyl propargylamide [ No CAS ]

Reference： [1]Chemical Communications,2000,p. 509 - 510
[2]Journal of Organometallic Chemistry,2001,vol. 637-639,p. 398 - 406

43
copper(II) choride dihydrate [ No CAS ]
[ 15430-52-1 ]
[ 380906-93-4 ]

Reference： [1]Russian Journal of Inorganic Chemistry,2001,vol. 46,p. 987 - 992

44
copper(II) choride dihydrate [ No CAS ]
ammonium chloride [ No CAS ]
[ 80937-33-3 ]
[ 15430-52-1 ]
[H₃NCH₂CCCCCH₂NH₃]Cu₂Cl₄ [ No CAS ]

Reference： [1]Russian Journal of Coordination Chemistry,2003,vol. 29,p. 261 - 264

45
[ 81-25-4 ]
[ 15430-52-1 ]
[ 1021182-35-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 3823 - 3830

46
[ 83-44-3 ]
[ 15430-52-1 ]
[ 1024746-93-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 3823 - 3830

47
[ 15430-52-1 ]
[ 122-04-3 ]
[ 52829-66-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine; In dichloromethane; at -40 - 20℃; for 24h;Inert atmosphere;	The reaction was run under an inert gas atmosphere (Ar). In a dried round-bottomed flask equipped with a septum <strong>[15430-52-1]propargylamine hydrochloride</strong> (740 mg, 8.08 mmol, 1.5 equiv) and triethylamine (12.4 mL) in 22 mL of dry dichloromethane were placed. Then the mixture was cooled to -40 C and a solution of 4-nitrobenzoyl chloride (1 g, 5.39 mmol, 1 equiv) in dry CH2Cl2 (22 mL) was added dropwise. The reaction was stirred for 24 h at room temperature. Afterwards the reaction was quenched by the addition of water (7.4 mL). After 10 minutes, additional 22 mL of water were added and the mixture extracted with CHCl3 (3 × 80 mL). The combined extracts were dried (MgSO4) and concentrated to give the crude product, which was purified by column chromatography (DCM/acetone 0-30%). Yield 1.080 g (98%) from 1 g(5.39 mmol) of 4-nitrobenzoyl chloride.
77%	With pyridine; In tetrahydrofuran; for 16h;Reflux;	To a stirred solution of <strong>[15430-52-1]propargylamine hydrochloride</strong> (5.0 g, 54.6mmol) and pyridine (7.8 g, 99.1 mmol) in tetrahydrofuran (3OmL) was added 4-nitro- benzoylchloride (9.2 g, 49.6 mmol) in tetrahydrofuran (20 mL) and the mixture was heated at reflux for 16 h. The mixture was allowed to cool to ambient temperature and concentrated in vacuo. The crude residue was dissolved in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, water, brine, dried over anhydrous sodium sulphate, filtered and concentrated in vacuo to afford 4-nitro-N-prop-2-ynyl- benzamide (7.74 g, 77%) as a solid.

Reference： [1]Beilstein Journal of Organic Chemistry,2020,vol. 16,p. 1436 - 1446
[2]Patent: WO2009/130481,2009,A1 .Location in patent: Page/Page column 138

48
[ 181697-00-7 ]
[ 15430-52-1 ]
[ 1204749-55-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4862 - 4888

49
[ 15430-52-1 ]
[ 88356-92-7 ]
[ 1204748-95-7 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4862 - 4888

50
[ 15430-52-1 ]
[ 200554-19-4 ]
[ 1239204-75-1 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5721 - 5731

51
N,N'-bis-(2-azidoethyl)-dodecane-1,12-diamine dihydrochloride [ No CAS ]
[ 15430-52-1 ]
[ 1197257-31-0 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 10360 - 10363

52
[ 71989-18-9 ]
[ 15430-52-1 ]
[ 917232-54-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4517 - 4525

53
[ 1219142-41-2 ]
[ 15430-52-1 ]
[ 1219142-06-9 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 1951 - 1967

54
[ 15430-52-1 ]
[ 103946-54-9 ]
[ 220715-46-8 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 2197 - 2199

55
[ 2450-71-7 ]
[ 15430-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In ethyl acetate; isopropyl alcohol; at 0 - 5℃;pH 2 - 5;	Propargylamine (200 g) is charged into a round bottom flask containing ethyl acetate (1500 mL) and stirred for about 10 minutes. The solution is cooled to 0-50C, pH is adjusted to 2-5 by addition of hydrogen chloride in isopropanol (18%, 1405 mL), and the mixture is stirred for solid formation. The solid is filtered and washed with ethyl acetate (400 mL), and then suction dried for about 30 minutes. The obtained solid is dried at 700C for 6-7 hours to afford 300 g of the title compound.
	With hydrogenchloride; In ethyl acetate; isopropyl alcohol; at 0 - 5℃;pH 2 - 5;	Propargylamine (200 g) is charged into a round bottom flask containing ethyl acetate (1500 mL) and stirred for about 10 minutes. The solution is cooled to 0-5 C., pH is adjusted to 2-5 by addition of hydrogen chloride in isopropanol (18%, 1405 mL), and the mixture is stirred for solid formation. The solid is filtered and washed with ethyl acetate (400 mL), and then suction dried for about 30 minutes. The obtained solid is dried at 70 C. for 6-7 hours to afford 300 g of the title compound.

Reference： [1]Patent: WO2010/59913,2010,A2 .Location in patent: Page/Page column 18
[2]Patent: US2011/218360,2011,A1 .Location in patent: Page/Page column 7

56
[ 15430-52-1 ]
[ 83-33-0 ]
[ 1875-50-9 ]

Yield	Reaction Conditions	Operation in experiment
89.6%		1 -lndanone (5 g), progargylamine hydrochloride (6.9 g), and methanol (50 mL) are charged into a round bottom flask and stirred for about 30 minutes at room temperature. To the solution, sodium acetate (3.1 g) and sodium cyanoborohydhde (2.37 g) are added, and then the mixture is heated to reflux and maintained for completion of the reaction. The mass is distilled completely under vacuum to produce a residue. Water (500 mL) is added to the residue, the pH is adjusted to 1-2 by addition of aqueous HCI (5 mL), the mixture is washed with toluene (2chi25 mL), and the aqueous layer is separated. The obtained aqueous layer pH is adjusted to 11 -13 by addition of caustic lye (5 mL) and extracted with ethyl acetate (2chi30 mL). The organic layer is separated, washed with water (2chi30 mL), and is distilled completely under vaccum to afford 5.8 g of the title compound as a residue (89.6% yield).
89.6%		1-Indanone (5 g), progargylamine hydrochloride (6.9 g), and methanol (50 mL) are charged into a round bottom flask and stirred for about 30 minutes at room temperature. To the solution, sodium acetate (3.1 g) and sodium cyanoborohydride (2.37 g) are added, and then the mixture is heated to reflux and maintained for completion of the reaction. The mass is distilled completely under vacuum to produce a residue. Water (500 mL) is added to the residue, the pH is adjusted to 1-2 by addition of aqueous HCl (5 mL), the mixture is washed with toluene (2×25 mL), and the aqueous layer is separated. The obtained aqueous layer pH is adjusted to 11-13 by addition of caustic lye (5 mL) and extracted with ethyl acetate (2×30 mL). The organic layer is separated, washed with water (2×30 mL), and is distilled completely under vacuum to afford 5.8 g of the title compound as a residue (89.6% yield).

Reference： [1]Patent: WO2010/59913,2010,A2 .Location in patent: Page/Page column 18
[2]Patent: US2011/218360,2011,A1 .Location in patent: Page/Page column 7

57
[ 29745-44-6 ]
[ 15430-52-1 ]
[ 866863-43-6 ]