[ CAS No. 88211-50-1 ] {[proInfo.proName]}

Name: 88211-50-1|But-3-yn-1-amine hydrochloride|95%
Brand: Ambeed
SKU: A196114
Price: 14.0 USD
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Quality Control of [ 88211-50-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 88211-50-1 ]

SDS Specification

Alternatived Products of [ 88211-50-1 ]

Product Details of [ 88211-50-1 ]

CAS No. :	88211-50-1	MDL No. :	MFCD06658391
Formula :	C₄H₈ClN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PQEPCBUBKRUREA-UHFFFAOYSA-N
M.W :	105.57	Pubchem ID :	12221022
Synonyms :

Calculated chemistry of [ 88211-50-1 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	29.18
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.48 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.66
Log Po/w (WLOGP) :	0.85
Log Po/w (MLOGP) :	1.01
Log Po/w (SILICOS-IT) :	0.03
Consensus Log Po/w :	0.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.84
Solubility :	15.1 mg/ml ; 0.143 mol/l
Class :	Very soluble
Log S (Ali) :	-0.78
Solubility :	17.4 mg/ml ; 0.165 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.27
Solubility :	57.2 mg/ml ; 0.542 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.87

Safety of [ 88211-50-1 ]

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

Application In Synthesis of [ 88211-50-1 ]

* 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 [ 88211-50-1 ]
Downstream synthetic route of [ 88211-50-1 ]

[ 88211-50-1 ] Synthesis Path-Upstream 1~7

1
[ 149990-27-2 ]
[ 88211-50-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With hydrogenchloride; water In dichloromethane at 20℃;	Preparation 18; iV-But-3-ynyl-2,2-dimethyl-ρropionamide; But-3-ynyl amine hydrochloride: Dissolve but-3-ynyl-carbamic acid tert-butyl ester (1.81 g, 0.1 mmol) in DCM (5 mL) and add 5N aqueous HCl (5 mL). Stir vigorously at room temperature overnight. Concentrate in vacuo to a minimum amount of volume and then freeze dry to obtain the desired material as a white solid (809 mg, 79percent).iV-But-3-ynyl-2,2-dimethγl-propionamide:; Add triethylamine (3 mL) to a suspension of but-3-ynylamine hydrochloride (200 mg, 2.1 mmol) in DCM (10 mL) and stir for 10 min at room temperature under nitrogen. Add then neat pivaloyl chloride (284.9 μL, 2.31 mmol) and stir at room temperature overnight under nitrogen. Concentrate in vacuo, take up the residue in methanol and filter through a SCX-2 cartridge eluting with methanol to obtain the title compound (265 mg, 65percent).

Reference： [1] Patent: WO2007/28131, 2007, A1, . Location in patent: Page/Page column 50

2
[ 10451-00-0 ]
[ 88211-50-1 ]

Yield	Reaction Conditions	Operation in experiment
1.25 g	Stage #1: With triphenylphosphine In diethyl ether at 0℃; for 2 h; Stage #2: With water In diethyl ether at 25℃; for 20 h; Stage #3: With hydrogenchloride In diethyl ether; water	5.5 g 3-Butynyl methanesulfonate of step 1.2 (24.5 mmol) was dissolved in 100 mL anhydrous dimethylformamide (DMF), and sodium azide (4 g, 61.4 mmol) added in portions. The reaction mixture was heated to 70 °C and stirred for 3.5 h, cooled to 25 °C and extracted with Et₂0 (50 mL x 3). The combined organic phase was washed with water, brine, and dried over Na₂S0₄. Volatile solvents were removed by rotary evaporation. The resulting residue containing 3-butyn-l-azide was used without further purification and was mixed with triphenyl phosphine (6.44 g, 24.4 mmol) in Et₂0 (100 mL) at 0° C and stirred for 2 h. Water (3.9 mL) was added and the resulting mixture stirred for an additional 20 h at 25 °C. The mixture was poured into IN HC1 (25 mL) and the aqueous layer extracted with Et₂0 (10 mL x 3). The remaining aqueous layer was concentrated under reduced pressure rotary evaporation to give 1.25 g 3-butyn-l-aminium chloride (49 percent yield for two steps).
1.25 g	Stage #1: With triphenylphosphine In diethyl ether at 0℃; for 2 h; Stage #2: With hydrogenchloride; water In diethyl ether	5.5 g 3-Butynyl methanesulfonate of step 1.2 (24.5 mmol) was dissolved in 100 mL anhydrous dimethylformamide(DMF), and sodium azide (4 g, 61.4 mmol) added in portions. The reaction mixture was heated to 70 °C and stirredfor 3.5 h, cooled to 25 °C and extracted with Et2O (50 mL 3 3). The combined organic phase was washed with water,brine, and dried over Na2SO4. Volatile solvents were removed by rotary evaporation. The resulting residue containing3-butyn-1-azide was used without further purification and was mixed with triphenyl phosphine (6.44 g, 24.4 mmol) inEt2O (100 mL) at 0° C and stirred for 2 h. Water (3.9 mL) was added and the resulting mixture stirred for an additional20 h at 25 °C. The mixture was poured into 1N HCl (25 mL) and the aqueous layer extracted with Et2O (10 mL 3 3).The remaining aqueous layer was concentrated under reduced pressure rotary evaporation to give 1.25 g 3-butyn-1-aminium chloride (49 percent yield for two steps

Reference： [1] Journal of the American Chemical Society, 2009, vol. 131, # 42, p. 15096 - 15097
[2] Chemistry - A European Journal, 2010, vol. 16, # 41, p. 12303 - 12306
[3] Patent: WO2013/117559, 2013, A1, . Location in patent: Page/Page column 28; 29
[4] Patent: EP2626356, 2013, A1, . Location in patent: Paragraph 0084

3
[ 927-74-2 ]
[ 88211-50-1 ]

Reference： [1] Synthesis, 1992, # 1-2, p. 146 - 150

4
[ 14396-90-8 ]
[ 1875-48-5 ]
[ 88211-50-1 ]

Reference： [1] Chemistry - A European Journal, 2010, vol. 16, # 41, p. 12303 - 12306

5
[ 14396-90-8 ]
[ 88211-50-1 ]

Reference： [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 25, p. 6214 - 6218

6
[ 14044-63-4 ]
[ 88211-50-1 ]

Reference： [1] Organic and Biomolecular Chemistry, 2010, vol. 8, # 9, p. 2164 - 2173

7
[ 88211-47-6 ]
[ 107-46-0 ]
[ 88211-50-1 ]

Reference： [1] Angewandte Chemie, 1984, vol. 96, # 1, p. 52

[ 88211-50-1 ] Synthesis Path-Downstream 1~85

1
[ 41143-14-0 ]
[ 88211-50-1 ]
[ 107409-28-9 ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 2788 - 2796

2
[ 88211-47-6 ]
[ 107-46-0 ]
[ 88211-50-1 ]

Reference： [1]Angewandte Chemie,1984,vol. 96,p. 52

3
[ 927-74-2 ]
[ 88211-50-1 ]

Reference： [1]Synthesis,1992,p. 146 - 150

4
[ 621-29-4 ]
[ 88211-50-1 ]
[ 915068-34-7 ]
3-But-3-ynyl-5,5-dimethyl-2-m-tolylamino-3,5-dihydro-imidazol-4-one [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 6581 - 6590

5
[ 4083-64-1 ]
[ 88211-50-1 ]
[ 915068-34-7 ]
N-(1-But-3-ynyl-4,4-dimethyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-4-methyl-benzenesulfonamide [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 6581 - 6590

6
[ 103-71-9 ]
[ 88211-50-1 ]
[ 915068-34-7 ]
3-But-3-ynyl-5,5-dimethyl-2-phenylamino-3,5-dihydro-imidazol-4-one [ No CAS ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 6581 - 6590

7
[ 88211-50-1 ]
[ 180893-42-9 ]
[ 180893-65-6 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 9161 - 9178

8
[ 88211-50-1 ]
[ 175468-52-7 ]
[ 180893-66-7 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 9161 - 9178

9
[ 88211-50-1 ]
[ 180893-43-0 ]
[ 180893-67-8 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 9161 - 9178

10
[ 123-11-5 ]
[ 88211-50-1 ]
[ 146980-79-2 ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 373 - 392

11
[ 98-88-4 ]
[ 88211-50-1 ]
[ 323581-08-4 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 2328 - 2336
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 8557 - 8577

12
[ 88211-50-1 ]
[ 1672-34-0 ]
[ 95209-18-0 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 9120 - 9124

13
[ 88211-50-1 ]
[ 431079-81-1 ]
[ 431079-82-2 ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 947 - 950

14
[ 3383-21-9 ]
[ 88211-50-1 ]
[ 1020-31-1 ]
5,7-di-tert-butyl-2-(1,2-propadienyl)benzoxazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 8038 - 8045

15
[ 3383-21-9 ]
[ 88211-50-1 ]
[ 1020-31-1 ]
5,7-di-tert-butyl-2-(2-propynyl)benzoxazole [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 8038 - 8045

16
[ 5396-30-5 ]
[ 88211-50-1 ]
[ 793668-05-0 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 12809 - 12818

17
[ 88211-50-1 ]
[ 656807-25-9 ]
N-3-butynyl-(2-ethynylphenyl)methylamine [ No CAS ]

Reference： [1]Heterocycles,2004,vol. 64,p. 467 - 474

18
[ 88211-50-1 ]
[ 530-62-1 ]
N-3-butyn-1-yl-1H-imidazole-1-carboxamide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2002,vol. 124,p. 11292 - 11294

19
[ 103-71-9 ]
[ 88211-50-1 ]
1-(but-3-ynyl)-3-(phenyl)urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; at 20℃;	General Procedure 2b (GP2b): Reaction of homopropargyl amine hydrochloride with isocyanatesA solution of homopropargyl amine hydrochloride in THF (0.3 M) was treated under a nitrogen atmosphere with triethylamine (1.5 eq.) and subsequently with the respective isocyanate (1.05 eq.). The resulting mixture was stirred at room <n="47"/>temperatur until TLC indicated complete turnover, evaporated and the resulting oil was triturated with hexane, filtered and the solid washed with additional ice-cold hexane to give the respective urea of sufficient purity for use without further purification.; The following Intermediate A to N were prepared by reaction of propargyl amine or homopropargyl amine hydrochloride with the respective isocyanate or sulfonyl chloride in analogy to the general procedures GP 2a, 2b, 3a or 3b as stated below the respective structures.

Reference： [1]Patent: WO2007/147575,2007,A2 .Location in patent: Page/Page column 44-45; 49; 51

20
[ 88211-50-1 ]
[ 98-09-9 ]
N-(but-3-yn-1-yl)benzenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile; at 20℃;	General Procedure 3a (GP 3a): Reaction of propargyl amine with sulfonyl chloridesA solution of propargyl amine in acetonitrile (0.3 M) was treated with the respective sulfonyl chloride (1.05 eq.) and triethyl amine (1.5 eq.) at room temperature under an atmosphere of nitrogen and stirred until TLC indicated complete turnover. The mixture was quenched with water, extracted with ethyl acetate, dried and concentrated in vacuo. The resulting crude product was either triturated with hexane or re-crystallized from acetone /hexane to yield the desired sulfonamide, which was typically used without further purification.; The following Intermediate A to N were prepared by reaction of propargyl amine or homopropargyl amine hydrochloride with the respective isocyanate or sulfonyl chloride in analogy to the general procedures GP 2a, 2b, 3a or 3b as stated below the respective structures.

Reference： [1]Patent: WO2007/147575,2007,A2 .Location in patent: Page/Page column 45; 49; 51

21
[ 63201-02-5 ]
[ 88211-50-1 ]
1-phenylcyclopropanecarboxylic acid prop-2-ynylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In acetonitrile; at 20℃; for 16h;	Intermediate PPreparation of 1 -Phenyl-cyclopropanecarboxylic acid but-3-ynylamide422 mg Homopropargylamine hydrochloride (4 mmol, 1 eq.) were suspended in 12 ml_ acetonitrile and treated with 1.11 ml_ triethylamine (8 mmol, 2 eq.) and subsequently portionwise with 722 mg phenylcyclopropylcarboxylic acid chloride (see above, 4 mmol, 1 eq.). This mixture was stirred at rt for 16h, diluted with ethyl acetate and quenched with water. The aqueous layer was extracted with ethyl acetate twice, the combined organic layers were washed with brine, dried and concentrated in vacuo to yield the crude amide as an off-white solid in quantitative yield. <n="56"/>1H-NMR (DMSO, 400 MHz): 7.22 - 7.33 (m, 5 H); 6.76 (t, 1 H); 3.08 (q, 2 H); 2.73 (t, 1 H); 2.18 (dt, 2 H); 1.28 - 1.30 (m, 2 H); 0.91 - 0.93 (m, 2 H). MS (ESI): [M+H]+ = 214.

Reference： [1]Patent: WO2007/147575,2007,A2 .Location in patent: Page/Page column 53

22
[ 93420-43-0 ]
[ 88211-50-1 ]
C₁₃H₁₆N₂O₃S₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 9964 - 9975

23
[ 108-30-5 ]
[ 88211-50-1 ]
[ 38018-23-4 ]

Reference： [1]Australian Journal of Chemistry,2008,vol. 61,p. 138 - 143

24
[ 85952-30-3 ]
[ 88211-50-1 ]
N-but-3-ynyl-1-(3,4-dichlorophenyl)methanesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium carbonate; In tetrahydrofuran; water; at 15 - 20℃; for 4.5h;	EXAMPLE 1 N-But-3-ynyl-1-(3.4-dichlorophenyl)methanesulfonamide To a mixture of potassium carbonate (40.2 g, 296 mmol) in water (50 mL) and THF (50 mL) at 15-20 C. was added but-3-ynylamine hydrogen chloride (10.4 g, 98.5 mmol). Then, (3,4-dichlorophenyl)methanesulfonyl chloride (5, 30.7 g, 118 mmol) was added in portions during of a period of 30 min. The mixture was stirred for 4 h at rt. THF is evaporated. The mixture is extracted with EtOAc (2x200 mL). The combined organic extracts were dried over Na2SO4. The solvent is evaporated to give a white solid (20.5 g, 71%). 1H NMR (CDCl3): delta7.53 (d, 1H, J=2.0 Hz), 7.47 (d, 1H, J=4.2 Hz), 7.27 (m, 1H), 4.52 (t, 1H, J=6.2 Hz), 4.22 (s, 2H), 3.17 (dd, 2H, J=6.2 Hz, 12.5 Hz), 2.41 (m, 2H), 2.07 (m, 1H)

Reference： [1]Patent: US2005/20858,2005,A1 .Location in patent: Page/Page column 5

25
[ 149990-27-2 ]
[ 88211-50-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With hydrogenchloride; water; In dichloromethane; at 20℃;	Preparation 18; iV-But-3-ynyl-2,2-dimethyl-rhoropionamide; But-3-ynyl amine hydrochloride: Dissolve but-3-ynyl-carbamic acid tert-butyl ester (1.81 g, 0.1 mmol) in DCM (5 mL) and add 5N aqueous HCl (5 mL). Stir vigorously at room temperature overnight. Concentrate in vacuo to a minimum amount of volume and then freeze dry to obtain the desired material as a white solid (809 mg, 79%).iV-But-3-ynyl-2,2-dimethgammal-propionamide:; Add triethylamine (3 mL) to a suspension of but-3-ynylamine hydrochloride (200 mg, 2.1 mmol) in DCM (10 mL) and stir for 10 min at room temperature under nitrogen. Add then neat pivaloyl chloride (284.9 muL, 2.31 mmol) and stir at room temperature overnight under nitrogen. Concentrate in vacuo, take up the residue in methanol and filter through a SCX-2 cartridge eluting with methanol to obtain the title compound (265 mg, 65%).

Reference： [1]Patent: WO2007/28131,2007,A1 .Location in patent: Page/Page column 50

26
[ 88211-50-1 ]
[ 13551-86-5 ]
[ 1021880-41-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; In methanol; for 5h;Heating / reflux;	A mixture of 5 (2.67 g, 13.1 mmol), but-3-ynylamine HCl salt (2.76 g, 26.2 mmol) and potassium carbonate (3.62 g) in 40 ml of methanol was refluxed for 5 h. After the workup, the residue was purified by column chromatography (THF-EtOH=9:0.5) to give 2.2 g of yellow solid (6, 70% yield). 1H NMR (DMSO-d6, deltappm): 2.26 (dt, 2H, ?C-CH2-, J=7.2 Hz, 2.7 Hz), 2.50(d, 2H, J=5.7 Hz), 2.63(t, 2H, J=7.2 Hz), 2.78(t, 1H, CH?C-, J=2.7 Hz), 3.82(m, 1H, HO-CH-), 4.25 (dd, 1H, imidazole-CHa-, J=13.8 Hz, 8.4 Hz), 4.54 (dd, 1H, imidazole-CHb-, J=13.8 Hz, 3.6 Hz), 5.13(d,1H, OH, J=5.1 Hz), 7.13(s, 1H, -CH), 7.55(s, 1H, -CH). 13C NMR (DMSO-d6, deltappm): 18.80, 47.79, 52.04, 52.89, 68.09, 71.60, 82.87, 126.98, 128.19, 144.83.

Reference： [1]Patent: US2008/102026,2008,A1 .Location in patent: Page/Page column 13; 17

27
[ 36743-66-5 ]
[ 88211-50-1 ]
[ 1191900-56-7 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 15096 - 15097

28
[ 10451-00-0 ]
[ 88211-50-1 ]

Yield	Reaction Conditions	Operation in experiment
1.25 g		5.5 g 3-Butynyl methanesulfonate of step 1.2 (24.5 mmol) was dissolved in 100 mL anhydrous dimethylformamide (DMF), and sodium azide (4 g, 61.4 mmol) added in portions. The reaction mixture was heated to 70 C and stirred for 3.5 h, cooled to 25 C and extracted with Et20 (50 mL x 3). The combined organic phase was washed with water, brine, and dried over Na2S04. Volatile solvents were removed by rotary evaporation. The resulting residue containing 3-butyn-l-azide was used without further purification and was mixed with triphenyl phosphine (6.44 g, 24.4 mmol) in Et20 (100 mL) at 0 C and stirred for 2 h. Water (3.9 mL) was added and the resulting mixture stirred for an additional 20 h at 25 C. The mixture was poured into IN HC1 (25 mL) and the aqueous layer extracted with Et20 (10 mL x 3). The remaining aqueous layer was concentrated under reduced pressure rotary evaporation to give 1.25 g 3-butyn-l-aminium chloride (49 % yield for two steps).
1.25 g		5.5 g 3-Butynyl methanesulfonate of step 1.2 (24.5 mmol) was dissolved in 100 mL anhydrous dimethylformamide(DMF), and sodium azide (4 g, 61.4 mmol) added in portions. The reaction mixture was heated to 70 C and stirredfor 3.5 h, cooled to 25 C and extracted with Et2O (50 mL 3 3). The combined organic phase was washed with water,brine, and dried over Na2SO4. Volatile solvents were removed by rotary evaporation. The resulting residue containing3-butyn-1-azide was used without further purification and was mixed with triphenyl phosphine (6.44 g, 24.4 mmol) inEt2O (100 mL) at 0 C and stirred for 2 h. Water (3.9 mL) was added and the resulting mixture stirred for an additional20 h at 25 C. The mixture was poured into 1N HCl (25 mL) and the aqueous layer extracted with Et2O (10 mL 3 3).The remaining aqueous layer was concentrated under reduced pressure rotary evaporation to give 1.25 g 3-butyn-1-aminium chloride (49 % yield for two steps

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 15096 - 15097
[2]Chemistry - A European Journal,2010,vol. 16,p. 12303 - 12306
[3]Patent: WO2013/117559,2013,A1 .Location in patent: Page/Page column 28; 29
[4]Patent: EP2626356,2013,A1 .Location in patent: Paragraph 0084

29
[ 785-56-8 ]
[ 88211-50-1 ]
[ 1207114-07-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 665 - 672

30
[ 918106-28-2 ]
[ 88211-50-1 ]
[ 1227736-75-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 2164 - 2173

31
[ 14044-63-4 ]
[ 88211-50-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 2164 - 2173

32
[ 14396-90-8 ]
[ 1875-48-5 ]
[ 88211-50-1 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 12303 - 12306

33
[ 15960-79-9 ]
[ 88211-50-1 ]
[ 1258538-11-2 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 12303 - 12306

34
[ 88211-50-1 ]
[ 685-87-0 ]
[ 1258538-10-1 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 12303 - 12306

35
[ 15159-40-7 ]
[ 88211-50-1 ]
[ 1293915-63-5 ]

Yield	Reaction Conditions	Operation in experiment
48%	With triethylamine; In dichloromethane; at 20℃;	To a suspension of but-3-yn-1 -amine hydrochloride (200 mg, 1 .89 mmol) and triethylamine (425 mu, 3.78 mmol) in DCM (60 mL) was added morpholine-4-carbonyl chloride (218 mu L, 1 .89 mmol). The reaction was stirred at RT overnight and then washed with aq hydrochloric acid (2 M, 2 x 20 mL), saturated aq sodium bicarbonate (2 x 20 mL), dried, filtered and evaporated in vacuo. The residue was purified by flash column chromatography, eluting with 0-100% ethyl acetate in heptane, to afford the title compound (13) (164 mg, 48%) as a white solid. 1H NMR (500 MHz, DMSO-de) delta : 2.28 (2H, td), 2.82 (1 H, t), 3.09-3.18 (2H, m), 3.20-3.27 (4H, m), 3.48- 3.57 (4H, m), 6.74 (1 H, t).
48%	With triethylamine; In dichloromethane; at 20℃;	N-(But-3-ynyl)morpholine-4-carboxamide (13) To a suspension of but-3-yn-1-amine hydrochloride (200 mg, 1.89 mmol) and triethylamine (425 muL, 3.78 mmol) in DCM (60 mL) was added morpholine-4-carbonyl chloride (218 muL, 1.89 mmol). The reaction was stirred at RT overnight and then washed with aq hydrochloric acid (2 M, 220 mL), saturated aq sodium bicarbonate (220 mL), dried, filtered and evaporated in vacuo. The residue was purified by flash column chromatography, eluting with 0-100% ethyl acetate in heptane, to afford the title compound (13) (164 mg, 48%) as a white solid. 1H NMR (500 MHz, DMSO-d6) delta: 2.28 (2H, td), 2.82 (1H, t), 3.09-3.18 (2H, m), 3.20-3.27 (4H, m), 3.48-3.57 (4H, m), 6.74 (1H, t).

Reference： [1]Patent: WO2011/48111,2011,A1 .Location in patent: Page/Page column 45-46
[2]Patent: US2012/208799,2012,A1 .Location in patent: Page/Page column 22

36
[ 22536-67-0 ]
[ 88211-50-1 ]
[ 1356542-34-1 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 47 - 52

37
[ 935476-81-6 ]
[ 88211-50-1 ]
[ 1372805-21-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 2684 - 2688

38
[ 3350-78-5 ]
[ 88211-50-1 ]
[ 1340154-38-2 ]