[ CAS No. 123-00-2 ] {[proInfo.proName]}

Name: 123-00-2|3-Morpholinopropan-1-amine|98%
Brand: Ambeed
SKU: A108533
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Quality Control of [ 123-00-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 123-00-2 ]

CAS No. :	123-00-2	MDL No. :	MFCD00006184
Formula :	C₇H₁₆N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UIKUBYKUYUSRSM-UHFFFAOYSA-N
M.W :	144.21	Pubchem ID :	61055
Synonyms :

Calculated chemistry of [ 123-00-2 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	44.25
TPSA :	38.49 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) :	-7.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	-0.69
Log Po/w (WLOGP) :	-0.71
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	0.56
Consensus Log Po/w :	0.15

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.1
Solubility :	114.0 mg/ml ; 0.792 mol/l
Class :	Very soluble
Log S (Ali) :	0.36
Solubility :	328.0 mg/ml ; 2.27 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-0.9
Solubility :	18.2 mg/ml ; 0.126 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 123-00-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501	UN#:	2735
Hazard Statements:	H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 123-00-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 123-00-2 ]
Downstream synthetic route of [ 123-00-2 ]

[ 123-00-2 ] Synthesis Path-Upstream 1~15

1
[ 4542-47-6 ]
[ 110-91-8 ]
[ 123-00-2 ]

Yield	Reaction Conditions	Operation in experiment
22%	With sodium tetrahydroborate; hydrogen; nickel dichloride In <i>tert</i>-butyl alcohol at 70℃; for 8 h;	Similarly to the described above, using sodium borohydride (0.6 g, 0.016 mol), 15 mL of tert-butanol, anhydrous nickel(II) chloride (1.0 g, 0.008 mol), and nitrile 1n (14 g, 0.1 mol). The reaction duration was 8h, the temperature was 70°C. Morpholine 9n, content 22 wt percent. Mass spectrum, m/e (I_rel, percent): 88.8 (2) [ M+2], 87.9 (59) [ M+ 1], 86.8 (67) [M], 86.0 (100), 56.9(86), 55.9 (98), 41.9 (28). 3-N-Morpholino-1-aminopropane 2n, content 59 wt percent. Mass spectrum, m/e(I_rel, percent): 145.0 (5) [ M+ 1], 128.0 (1.5), 126.8 (7),113.0 (32), 101.0 (11), 100.0 (100), 86.0 (7), 72.0 (10),70.0 (30), 57.0 (11), 56.0 (35), 42.0 (30).

Reference： [1] Russian Journal of General Chemistry, 2016, vol. 86, # 2, p. 273 - 280[2] Zh. Obshch. Khim., 2016, vol. 86, # 2, p. 245 - 252,8

2
[ 4542-47-6 ]
[ 123-00-2 ]

Reference： [1] Journal of the Indian Chemical Society, 1958, vol. 35, p. 205,208,209
[2] Journal of the American Chemical Society, 1944, vol. 66, p. 725,728
[3] Patent: US2883370, 1954, ,
[4] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 6, p. 675 - 680

3
[ 110-91-8 ]
[ 6276-54-6 ]
[ 123-00-2 ]

Reference： [1] Patent: CN107619390, 2018, A, . Location in patent: Paragraph 0015

4
[ 106018-95-5 ]
[ 123-00-2 ]

Reference： [1] Tetrahedron Letters, 1986, vol. 27, # 19, p. 2099 - 2102

5
[ 4542-47-6 ]
[ 123-00-2 ]
[ 18889-29-7 ]

Reference： [1] Journal of the American Chemical Society, 1944, vol. 66, p. 725,728

6
[ 6820-95-7 ]
[ 123-00-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 6, p. 1593 - 1597
[2] ACS Chemical Neuroscience, 2015, vol. 6, # 8, p. 1317 - 1330
[3] European Journal of Medicinal Chemistry, 2016, vol. 109, p. 124 - 133

7
[ 80500-17-0 ]
[ 123-00-2 ]
[ 119-61-9 ]

Reference： [1] Journal of the American Chemical Society, 1982, vol. 104, # 3, p. 730 - 736

8
[ 23159-07-1 ]
[ 123-00-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2131 - 2135

9
[ 104712-03-0 ]
[ 123-00-2 ]

Reference： [1] Pharmaceutical Chemistry Journal, 1985, vol. 19, # 7, p. 479 - 481[2] Khimiko-Farmatsevticheskii Zhurnal, 1985, vol. 19, # 7, p. 829 - 832

10
[ 110-91-8 ]
[ 5460-29-7 ]
[ 123-00-2 ]

Reference： [1] Journal of the American Chemical Society, 1941, vol. 63, p. 156,158

11
[ 110-91-8 ]
[ 42251-84-3 ]
[ 123-00-2 ]

Reference： [1] Zhurnal Obshchei Khimii, 1938, vol. 8, p. 56,62[2] Chem. Zentralbl., 1940, vol. 111, # I, p. 548

12
[ 7357-67-7 ]
[ 1074-82-4 ]
[ 123-00-2 ]

Reference： [1] Farmaco, Edizione Scientifica, 1958, vol. 13, p. 261,282

13
[ 503-29-7 ]
[ 110-91-8 ]
[ 123-00-2 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1991, vol. 61, # 8.2, p. 1700 - 1713[2] Zhurnal Obshchei Khimii, 1991, vol. 61, # 8, p. 1841 - 1856

14
[ 110-91-8 ]
[ 107-13-1 ]
[ 123-00-2 ]
[ 18889-29-7 ]

Reference： [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1953, vol. 236, p. 1976

15
[ 123-00-2 ]
[ 1380432-31-4 ]
[ 1380432-32-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine In iso-butanol at 120℃; for 0.5 h; Microwave irradiation	₄Synthesis of EHop-016 [0031] ¹H and ¹³C NMR spectra were recorded on a Bruker 400 MHz Spectrometer. Mass spectra were obtained on a Hewlett Packard 6890N GC/MS Spectrometer. All chemicals were purchased from Sigma Aldrich Chemical Company. The synthesis of EHop-016 (5) was performed in two steps according to the reaction scheme provided in FIG. 1(A), and carried out analogous to the procedure described in (58). (2-Chloro-pyrimidin-4-yl)-(9-ethyl-9H-carbazol-3-yl)-amine 3 was obtained as a pure compound in a yield of 53percent. The product was identified with TLC, NMR and GC/MS. R_f=0.23 (3:1, Hexane-Ethyl Acetate); ¹H NMR (DMSO-d₆, 400 MHz) δ 1.32 (t, J=6.9 Hz, 3H), 4.45 (q, J=6.6 Hz, 2H), 6.72 (s, 1H), 7.20 (t, J=7.36 Hz, 1H), 7.47 (t, J=7.30 Hz, 1H), 7.56 (s, 1H), 7.62 (t, J=8.68 Hz, 1H), 8.11 (t, J=7.36 Hz, 1H), 8.27 (s, 1H), 10.1 (s, 1H); ¹³C (DMSO-d₆, 100 MHz) δ 13.7, 37.0, 109.2, 109.4, 115.0, 118.7, 120.3, 121.3, 121.9, 122.3, 125.9, 129.9, 136.9, 140.0, 156.9, 159.6, 162.4; LRGC-MS m/z (rel percent):[M]⁺ 276 (100), [M-Cl]⁺ 241 (40), [M-C₅H₅N₃Cl]⁺ 134 (26). N⁴-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-morpholin-4-yl-propyl)-pyrimidine-2,4-diamine 5 (EHop-016) was obtained as a pure compound in a yield of 93percent. The product was identified to be essentially pure by TLC and NMR: R_f=0.34 (9:1, CH₂Cl₂—MeOH); ¹H NMR (DMSO-d₆, 400 MHz) δ 1.31 (t, J=7.0 Hz, 3H), 1.73 (m, 2H), 2.32 (m, 2H), 2.34 (t, J=6.89 Hz, 8H), 3.52 (m, 2H), 4.42 (q, J=7.0 Hz, 2H), 5.98 (d, J=5.7 Hz, 1H), 6.69 (t, J=5.3 Hz, 1H), 7.16 (t, J=7.4, 1H), 7.43 (t, J=7.2 Hz, 1H), 7.53 (t, J=9.0 Hz, 4H), 7.81 (d, J=5.4 Hz, 1H), 8.10 (s, 1H), 8.66 (s, 1H), 9.1 (s, 1H); ¹³C (DMSO-d₆, 100 MHz) δ 13.7, 26.2, 36.9, 53.4, 56.3, 66.2, 108.9, 109.0, 118.2, 119.7, 120.2, 122.0, 122.2, 125.6, 132.5, 135.5, 139.9, 159.8, 160.9, 162.1.

Reference： [1] Patent: US2013/172552, 2013, A1, . Location in patent: Paragraph 0031

[ 123-00-2 ] Synthesis Path-Downstream 1~88

1
[ 123-00-2 ]
[ 121-60-8 ]
[ 77283-38-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate; In acetone; at 20℃; for 2.25h;	Example 6 <n="15"/>Preparation of 4-acetamido-N-(3-morpholinopropyl)benzenesulphonamide XIII; [Goldberg, M. W., Moutclair, U., US. Pat. 2.879.293 (1959)]To the solution of 2.8 g (0.020 mol) of 3-morpholinopropylamine in 15 ml of acetone, the solution of 3.3 g (0.024 mol) of potassium carbonate in 3 ml of water was added under stirring. To this mixture, 5 g (0.021 mol) of 4-acetamidobenzenesulphonyl chloride XII was added portionwise at the room temperature for 15 min. The mixture was then stirred at the room temperature for another 2 hours. One half of the solvent volume was distilled off from the mixture, the mixture was cooled to 0 0C, Obtained solid was separated, washed 3 times with 5 ml of ice water and dried. Afforded 4,2 g (62 %) of 4-acetamido-N-(3-morpholinopropyl)benzenesulphonamide XIII, colourless solid, m.p. 97-98 0C.

Reference： [1]Patent: WO2008/130332,2008,A1 .Location in patent: Page/Page column 9; 13-14
[2]Journal of the American Chemical Society,1944,vol. 66,p. 725,728

2
[ 123-00-2 ]
[ 4355-31-1 ]
[ 110195-31-8 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1164,1175

3
[ 123-00-2 ]
[ 403-16-7 ]
[ 896-03-7 ]

Reference： [1]Journal of the Chemical Society,1963,p. 2784 - 2787

4
[ 123-00-2 ]
[ 14527-26-5 ]
[ 13910-60-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1967,vol. 15,p. 228 - 232

5
[ 123-00-2 ]
[ 1074-40-4 ]
[ 104665-82-9 ]

Reference： [1]Journal of the Indian Chemical Society,1960,vol. 37,p. 617 - 620

6
[ 123-00-2 ]
[ 6492-86-0 ]
[ 58232-30-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 849 - 855

7
[ 123-00-2 ]
[ 3885-38-9 ]
2-methyl-3-<N-(3-morpholinopropyl)carbamoyl>quinoxaline [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1994,vol. 31,p. 33 - 38

8
[ 123-00-2 ]
[ 33045-53-3 ]
[ 102535-22-8 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 797 - 808
[2]Journal of Medicinal Chemistry,1986,vol. 29,p. 1814 - 1820

9
[ 123-00-2 ]
[ 373627-25-9 ]
[ 138767-72-3 ]

Reference： [1]Pharmaceutical Chemistry Journal,1991,vol. 25,p. 760 - 763
Khimiko-Farmatsevticheskii Zhurnal,1991,vol. 25,p. 10 - 13

10
[ 123-00-2 ]
[ 63875-01-4 ]
[1-(2-Methyl-pyridin-4-yl)-meth-(E)-ylidene]-(3-morpholin-4-yl-propyl)-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3929 - 3937

11
[ 123-00-2 ]
[ 18206-06-9 ]
[1-(2,6-Dimethyl-pyridin-4-yl)-meth-(E)-ylidene]-(3-morpholin-4-yl-propyl)-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 3929 - 3937

12
[ 123-00-2 ]
[ 63875-01-4 ]
2-methylpyridine-4-carboxaldehyde [3-(4-morpholinyl)propyl]imine [ No CAS ]

Reference： [1]Patent: EP1229035,2002,A1 .Location in patent: Page 23
[2]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 49 - 64
[3]Patent: EP1227092,2002,A2 .Location in patent: Page 23

13
[ 123-00-2 ]
[ 18206-06-9 ]
[1-(2,6-Dimethyl-pyridin-4-yl)-meth-(E)-ylidene]-(3-morpholin-4-yl-propyl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1997,vol. 5,p. 49 - 64

14
[ 123-00-2 ]
[ 55447-00-2 ]
[ 200864-76-2 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 199 - 223

15
[ 123-00-2 ]
[ 1004-17-7 ]
[1-(2-Methyl-pyrimidin-4-yl)-meth-(Z)-ylidene]-(3-morpholin-4-yl-propyl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 3111 - 3116

16
[ 123-00-2 ]
[ 1074-68-6 ]
[1-(2-Methylsulfanyl-pyrimidin-4-yl)-meth-(Z)-ylidene]-(3-morpholin-4-yl-propyl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,1998,vol. 8,p. 3111 - 3116

17
[ 123-00-2 ]
[ 34117-90-3 ]
N²-(3-morpholin-4-yl-propyl)-quinoxaline-2,3-diamine [ No CAS ]

Reference： [1]Acta poloniae pharmaceutica,1999,vol. 56,p. 201 - 206

18
[ 123-00-2 ]
[ 108-77-0 ]
[ 14002-33-6 ]
C₈₃H₁₄₅N₃₃O₁₃ [ No CAS ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 493 - 496

19
[ 123-00-2 ]
[ 1955-46-0 ]
[ 32315-10-9 ]
[ 124-40-3 ]
5-(3,3-dimethyl-ureido)-N-(3-morpholin-4-yl-propyl)-isophthalamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1998,vol. 8,p. 187 - 205

20
[ 123-00-2 ]
[ 1955-46-0 ]
PhOCH₂COOX (X=OH or Cl) [ No CAS ]
5-(4-morpholin-4-yl-butyrylamino)-N-phenoxymethyl-isophthalamide [ No CAS ]

Reference： [1]Medicinal Chemistry Research,1998,vol. 8,p. 187 - 205

21
[ 123-00-2 ]
[ 69812-29-9 ]
[ 16590-41-3 ]
C₃₃H₄₅N₅O₇S₂ [ No CAS ]

Reference： [1]Synlett,2002,p. 92 - 96

22
[ 123-00-2 ]
[ 309964-23-6 ]
4-{3-methoxy-4-[(3-morpholin-4-yl-propylamino)-methyl]-phenoxy}-butyric acid [ No CAS ]

Reference： [1]Tetrahedron Letters,2002,vol. 43,p. 3555 - 3556

23
[ 123-00-2 ]
[ 882-09-7 ]
[ 13734-34-4 ]
2-(4-chloro-phenoxy)-2-methyl-N-[1-(3-morpholin-4-yl-propylcarbamoyl)-2-phenyl-ethyl]-propionamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 585 - 588

24
[ 123-00-2 ]
[ 882-09-7 ]
[ 18942-49-9 ]
2-(4-chloro-phenoxy)-2-methyl-N-[1-(3-morpholin-4-yl-propylcarbamoyl)-2-phenyl-ethyl]-propionamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 585 - 588

25
[ 123-00-2 ]
[ 14527-26-5 ]
N-(3-morpholin-4-yl-propyl)-guanidine hydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 2397 - 2411

26
[ 123-00-2 ]
[ 83664-33-9 ]
[ 861884-74-4 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 4621 - 4625

27
[ 123-00-2 ]
[ 1070-70-8 ]
polymer, Mw = 9100, PDI = 2.53; monomer(s): 1,4-butanediol diacrylate; 4-(3-aminopropyl)morpholine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 8155 - 8156

28
[ 123-00-2 ]
[ 13048-33-4 ]
polymer, Mw = 11900, PDI = 2.18; monomer(s): 1,6-hexanediol diacrylate; 4-(3-aminopropyl)morpholine [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 8155 - 8156

29
[ 123-00-2 ]
(E)-3-[3-(1H-indol-3-yl)acrylamido]benzoic acid [ No CAS ]
(E)-3-(3-(1H-indol-3-yl-acryloylamino))-N-(3-morpholin-4-yl-propyl)-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	EXAMPLE 8: Preparation of 3- (3-lNo.-indol-3-yl-acryloylamino) -N- (3-morpholin-4-yl-propyl) -benzamide; In 5.0 mL of dimethylformamide were dissolved 3-(3-1H- indol-3-yl-acryloylamino) -benzoic acid (150 mg, 0.49 mmol) , prepared in Example 3, and 3-morpholin-4-yl-propylamine (0.11 mL, 0.73 mmol), followed by the addition of O- (7- azabenzotriazol-1-yl) -N, N, N' , N' -tetramethyl uronium <n="31"/>hexafluorophosphate (277.6 mg, 0.73 rnmol) and N,N- diisopropylethylamine (0.13 ml, 0.73 mmol) . The resulting solution was stirred at room temperature and mixed with ethyl acetate and an aqueous sodium salt solution. The organic layer was dried over anhydrous magnesium sulfate. After the filtration and concentration of the residue, the concentrate was purified using Prep-TLC (methylene chloride:methanol = 10:1) to produce the subject compound as a yellow solid (8)(92.6 mg, 44%) . 1H-NMR (DMSO-de, 300Hz): 11.66 (IH, brs, aromatic), 10.14(IH, s, aromatic), 8.46(1H, ps t, J= 5.4 Hz, aromatic), 8.09(IH, s, aromatic), 7.76-7.98 (4H, m, aromatic), 7.37-7.50 (3H, m, aromatic), 7.22 (2H, m, aromatic), 6.82 (IH, d, J = 15.9 Hz, aromatic), 3.55-3.59 (4H, m, aliphatic), 3.27 (IH, m, aliphatic), 3.16 (IH, d, J = 15.9 Hz, aliphatic), 2.31-2.36(6H, m, aliphatic) 1.69 (2H, m, aliphatic).
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃;	1-15. Synthesis of low-molecular-weight compound ID-265 (10c) The low-molecular-weight compound ID-265 (3-(3-1H-indol-3-yl-acrylamino)-N-(3-morpholin-4-yl-propyl)-benzamide) was prepared in the following manner. 3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid (9, 150 mg, 0.49 mmol) and 3-morpholin-4-yl-propylamine (0.11 mL, 0.73 mmol) were dissolved in DMF, and HATU (277.6 mg, 0.73 mmol) and DIPEA (0.13 mL, 0.73 mmol) were added thereto. The reaction solution was stirred overnight at room temperature. The resulting material was separated and purified to obtain 3-(3-1H-indol-3-yl-acryloylamino)-N-(3-morpholin-4-yl-propyl)-benzamide (ID-265) as a yellow solid. 1H NMR (DMSO-d3, 300 MHz) d = 11.66 (b, 1H), 10.14 (s, 1H), 8.46 (ps-t, J = 5.4 Hz, 1H), 8.09 (s, 1H), 7.76-7.98 (m, 4H), 7.37-7.50 (m, 3H), 7.22 (m, 2H), 6.82 (d, J = 15.9 Hz, 1H), 3.55-3.59 (m, 4H), 3.27 (m, 1H), 3.16 (d, J = 15.9 Hz, 1H), 2.31-2.36 (m, 6H) 1.69 (m, 2H).
	With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide;	1-15. Synthesis of Low-Molecular-Weight Compound ID-265 (10c) The low-molecular-weight compound ID-265 (3-(3-1H-indol-3-yl-acrylamino)-N-(3-morpholin-4-yl-propyl)-benzamide) was prepared in the following manner. 3-(3-1H-indol-3-yl-acryloylamino)-benzoic acid (9, 150 mg, 0.49 mmol) and 3-morpholin-4-yl-propylamine (0.11 mL, 0.73 mmol) were dissolved in DMF, and HATU (277.6 mg, 0.73 mmol) and DIPEA (0.13 mL, 0.73 mmol) were added thereto. The reaction solution was stirred overnight at room temperature. The resulting material was separated and purified to obtain 3-(3-1H-indol-3-yl-acryloylamino)-N-(3-morpholin-4-yl-propyl)-benzamide (ID-265) as a yellow solid. 1H NMR (DMSO-d3, 300 MHz) d=11.66 (b, 1H), 10.14 (s, 1H), 8.46 (ps-t, J=5.4 Hz, 1H), 8.09 (s, 1H), 7.76-7.98 (m, 4H), 7.37-7.50 (m, 3H), 7.22 (m, 2H), 6.82 (d, J=15.9 Hz, 1H), 3.55-3.59 (m, 4H), 3.27 (m, 1H), 3.16 (d, J=15.9 Hz, 1H), 2.31-2.36 (m, 6H) 1.69 (m, 2H).

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12509 - 12513
Angew. Chem.,2012,vol. 124,p. 12677 - 12681,5
[2]Patent: WO2008/39007,2008,A1 .Location in patent: Page/Page column 29-30
[3]Patent: EP2774918,2014,A1 .Location in patent: Paragraph 0126; 0149-0150
[4]Patent: US2015/159142,2015,A1 .Location in patent: Page/Page column

30
[ 123-00-2 ]
[ 6314-28-9 ]
[ 86123-10-6 ]
[ 117322-30-2 ]
MEN 14268 [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4841 - 4844

31
[ 123-00-2 ]
[ 6314-28-9 ]
[ 86123-10-6 ]
[ 135944-07-9 ]
C₃₅H₃₈N₄O₄S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4841 - 4844

32
[ 123-00-2 ]
[ 677297-51-7 ]
C₂₅H₂₇N₇O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4279 - 4294

33
[ 123-00-2 ]
[ 677297-51-7 ]
C₃₂H₄₀N₈O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4279 - 4294

34
[ 123-00-2 ]
[ 101066-61-9 ]
2-chloropyridine-4-carboxaldehyde [3-(4-morpholinyl)propyl]imine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		This aldehyde was reacted with 4-(3-aminopropyl)morpholine by the procedure of example 1(c) to afford the title compound as a yellow oil. 1 H NMR (CD3 Cl): delta8.45 (d, J=5.1 Hz, 1H), 8.24 (s, 1H), 7.63 (s, 1H); 7.51 (d, J=5.1 Hz, 1H), 3.72 (m, 6H), 2.44 (m, 6H), 1.91 (m, 2H).
		This aldehyde was reacted with 4-(3-aminopropyl)morpholine by the procedure of example 1(c) to afford the title compound as a yellow oil. 1 H NMR (CD3 Cl): delta8.45 (d, J=5.1 Hz, 1H), 8.24 (s, 1H), 7.63 (s, 1H); 7.51 (d, J=5.1 Hz, 1H), 3.72 (m, 6H), 2.44 (m, 6H), 1.91 (m, 2H).
		This aldehyde was reacted with 4-(3-aminopropyl)morpholine by the procedure of example 1(c) to afford the title compound as a yellow oil. 1 H NMR (CD3 Cl): delta 8.45 (d, J=5.1 Hz, 1H), 8.24(s, 1H),7.63 (s, 1H); 7.51 (d, J=5.1Hz, 1H), 3.72 (m, 6H), 2.44 (m, 6H), 1.91 (m, 2H).

Reference： [1]Patent: US5593991,1997,A
[2]Patent: US5593992,1997,A
[3]Patent: US5670527,1997,A
[4]Patent: EP1227092,2002,A2 .Location in patent: Page 23

35
[ 123-00-2 ]
[ 1074-68-6 ]
[ 165807-15-8 ]

Reference： [1]Patent: EP1227092,2002,A2 .Location in patent: Page 29
[2]Patent: EP1229035,2002,A1 .Location in patent: Page 29-30

36
[ 123-00-2 ]
[ 171489-59-1 ]
(6R,12AR)-6-benzo[1,3]dioxol-5-yl-2-(3-morpholin-4-ylpropyl)-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione [ No CAS ]

Reference： [1]Patent: US2003/225094,2003,A1 .Location in patent: Page 11

37
[ 123-00-2 ]
[ 2597-56-0 ]
[ 617244-91-4 ]

Yield	Reaction Conditions	Operation in experiment
94%		2-methoxy-4-nitro-benzoic acid (3.0 g, 15.5 MMOL) was dissolved in THF (180 ML) and the mixture was heated to reflux (70 C). CARBONYL DIIMIDAZOL (3.7 g, 22.8 MMOL) was added in 3 portions with 20 minutes intervals-with continued refluxing. After the last addition reaction is allowed to reflux for another 1 h. The reaction mixture was cooled to room temperature followed by addition of 3-morpholin-4-yl-propylamine (4.4 g, 30.4 MMOL) and the reaction was left overnight. The solvent was removed in vacuo and to the crude product was added a mixture of 200 ML EtOAc and 200 ml of water. The organic phase is washed with 2200 ml water and 1 200 ML of brine. The combined organic phases was dried over MGS04 AND concentrated giving a clear oil. Crystallisation can be obtained by adding diethylether followed by evaporation. The product (7.6 g, 23 MMOL) was dissolved in methanol (120 ml) and 10 % Pd/C (40 mg) was added. A pressure of hydrogen atmosphere was applied and the reaction was left over night. Filtration through a plug of celite gave 7.36 g of the title product (94 % over all yield). 'H-NMR (300 MHz, CD3CI) : S 1H, 7.79 (s, 1H), 4.03 (s, 2H), 3.90 (s, 3H).

Reference： [1]Patent: WO2004/48319,2004,A1 .Location in patent: Page 38-39

38
[ 123-00-2 ]
[ 793684-49-8 ]
5-Oxo-5,7-dihydro-6H-indeno[2,1-c]isoquinoline-9-sulfonic acid (3-morpholin-4-yl-propyl)-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With triethylamine; In dichloromethane; at 20℃; for 1h;	A suspension of 10a (110 mg, 0.33 mmol) in methylene chloride (10 mL) was treated with 4-(3-morpholino)-1-propylamine (240 mg, 1.66 mmol) and triethylamine (1 eq), and the reaction mixture was stirred at room temperature for 1 h. The resulting mixture was diluted with ethyl acetate, and the solid that precipitated was filtered, washed with ether and dried to provide compound 11a. Yield=65 mg (45%).
45%	With triethylamine; In dichloromethane; at 20℃; for 1h;	5-123f) 5-Oxo-5,7-dihydro-6H-indeno[2,1-c]isoquinoline-9-sulfonic acid (3-morpholin-4-yl-propyl)-amide (11a) (Scheme 1-123) A suspension of 10a (110 mg, 0.33 mmol) in methylene chloride (10 mL) was treated with 4-(3-morpholino)-1-propylamine (240 mg, 1.66 mmol) and triethylamine (1 eq), and the reaction mixture was stirred at room temperature for 1 h. The resulting mixture was diluted with ethyl acetate, and the solid that precipitated was filtered, washed with ether and dried to provide compound 11a. Yield=65 mg (45%).

Reference： [1]Patent: US2004/229895,2004,A1 .Location in patent: Page 26-27; 45
[2]Patent: US2006/19980,2006,A1 .Location in patent: Page/Page column 61

39
[ 123-00-2 ]
[ 753924-79-7 ]
[ 753925-20-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20℃; for 36h;	Example 53 Preparation of 5-(4-fluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid (3-morpholin-4-yl-propyl)-amide (11g-8) A solution of 5-(4-fluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid (compound 10g, prepared as described in Example 46) in THF was treated with carbonyldiimidazole (1.2 equivalents) at room temperature under nitrogen atmosphere.After stirring for 18 hours, the reaction was treated with 3-morpholin-4-yl-propylamine (1 equivalent).After an additional 18 hours, the solvent was allowed to slowly evaporate and the residue was purified in a Sep Pak cartridge eluding with a gradient of 100% CH2Cl2 to 5% MeOH/CH2Cl2 to provide compound 11g-8 as an oil in 70% yield.
70%	With 1,1'-carbonyldiimidazole; In tetrahydrofuran; dichloromethane;	Example 53 Preparation of 5-(4-fluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid (3-morpholin-4-yl-propyl)-amide (11g-8) A solution of 5-(4-fluorophenoxy)-1-isobutyl-1H-indazole-6-carboxylic acid (compound 10g, prepared as described in Example 46) in THF was treated with carbonyldiimidazole (1.2 equivalents) at room temperature under nitrogen atmosphere. After stirring for 18 hours, the reaction was treated with 3-morpholin-4-yl-propylamine (1 equivalent). After an additional 18 hours, the solvent was allowed to slowly evaporate and the residue was purified in a Sep Pak cartridge eluding with a gradient of 100% CH2Cl2 to 5% MeOH/CH2Cl2 to provide compound 11g-8 as an oil in 70% yield.

Reference： [1]Patent: US2004/176325,2004,A1 .Location in patent: Page/Page column 32; sheet 35
[2]Patent: US2004/180896,2004,A1

40
[ 123-00-2 ]
[ 98-61-3 ]
[ 403793-23-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at 0 - 20℃; for 0.5h;	4-Iodophenylsulphonyl chloride (3.03 g, 10 mmol) in DCM (30 ml) was added dropwise over 15 minutes to a solution of 4-(3-aminopropyl)morpholine (1.75 ml, 12 mmol) and triethylamine (1.7 ml, 12 mmol) in DCM (50 ml) cooled in an ice bath. The mixture was allowed to warm to ambient temperature and stirred for 15 minutes. Water (50 ml) was added and the phases separated. The organic layer was washed with water (50 ml) and brine (50 ml), dried (Chemelut column 1010) and evaporated to give the title compound (4.10 g, 100%) as a beige solid. NMR 1.70 (m, 21), 2.43 (m, 61, 3.14 (t, 2H), 3.71 (m, 4H), 7.08 (s, 1H), 7.58 (d, 2H), 7.85 (d, 2H); m/z 411.

Reference： [1]Patent: US2004/14776,2004,A1 .Location in patent: Page/Page column 36

41
[ 123-00-2 ]
[ 32779-36-5 ]
[ 886365-73-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 80℃; for 3h;	Intermediate 36; (5-Bromo-pyrimidin-2-yl)-(3-morpholin-4-yl-propyl)-amine2-Chloro-5-bromopyrimidine (50 g) was added to propan-2-ol (300 mL), DIPEA (92 mL) and aminopropylmorpholine (46 mL) and the reaction was heated at 8O0C for 3 hours. The reaction was allowed to cool and the solvent removed in vacuo to yield an orange gum, this was quenched with water (200 mL), extracted with diethyl ether (3 x 600 mL), dried(MgSO4) and solvent removed in vacuo to yield a yellow viscous oil. Diethyl ether (100 mL) was rapidly added to the gum with scratching until a solid crashed out, this was filtered. Process repeated on the filtered mother liquor until no solid crashed out. The obtained solids were combined and stirred in iso-hexane (200 mL) for 20 mins before being filtered and dried. White solid obtained (67g, 86%);1H NMR (300.072 MHz, cdcl3) delta 8.25 (s, 2H), 6.02 (s, IH), 3.73 (t, 4H), 3.45 (q, 2H), 2.49 - 2.44 (m, 6H), 1.78 (quintet, 2H); MS m/e MH+ 302.
86%	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 80℃; for 3h;	(5-Bromo-pyrimidin-2-yl)-(3-morpholin-4-yl-propyl)-amine 2-Chloro-5-bromopyrimidine (50 g) was added to propan-2-ol (300 mL), DIPEA (92 mL) and aminopropylmorpholine (46 mL) and the reaction was heated at 80 C. for 3 hours. The reaction was allowed to cool and the solvent removed in vacuo to yield an orange gum, this was quenched with water (200 mL), extracted with diethyl ether (3*600 mL), dried (MgSO4) and solvent removed in vacuo to yield a yellow viscous oil. Diethyl ether (100 mL) was rapidly added to the gum with scratching until a solid crashed out, this was filtered. Process repeated on the filtered mother liquor until no solid crashed out. The obtained solids were combined and stirred in iso-hexane (200 mL) for 20 mins before being filtered and dried. White solid obtained (67 g, 86%); 1H NMR (CDCl3) delta 8.25 (s, 2H), 6.02 (s, 1H), 3.73 (t, 4H), 3.45 (q, 2H), 2.49-2.44 (m, 6H), 1.78 (quintet, 2H); MS m/e MH+302.

Reference： [1]Patent: WO2006/82373,2006,A1 .Location in patent: Page/Page column 124
[2]Patent: US2008/194552,2008,A1 .Location in patent: Page/Page column 43

42
[ 123-00-2 ]
[ 24424-99-5 ]
(3-morpholin-4-ylpropyl)carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine; In dichloromethane; at 25℃;	Into a 100-mL round-bottom flask, was placed a solution of 3-morpholinopropan-1-amine (5 g, 34.67 mmol, 1.00 equiv) in dichloromethane (50 mL), di-tert-butyl dicarbonate (7.56 g, 34.67 mmol, 1.00 equiv.), triethylamine (7 g, 70.00 mmol, 2.00 equiv). The resulting solution was stirred overnight at 25 C. The resulting mixture was concentrated under vacuum. This resulted in 6.8 g (80%) of tert-butyl 3-morpholinopropylcarbamate as light yellow oil.
	In dichloromethane;	A. To a solution of 4-(3-aminopropyl)morpholine (50.0 g, 0.347 mol) in CH2Cl2 (250 mL) at approximately 0 C. was added a solution of Di-tert-butyl dicarbonate (75.5 g, 0.347 mol) in CH2Cl2 (250 mL). The reaction mixture was stirred at 0 C. for 1 hour then at room temperature for 14 hours. The reaction mixture was then washed with saturated aqueous NaHCO3 and water. The organic layer was then dried over Na2SO4, filtered and the filtrate concentrated in vacuo to provide 4-(3-(tert-butoxycarbonylamino)propyl)morpholine as a clear oil. 1H-NMR (300 MHz, DMSO-d6): delta 6.75 (t, 1H, J=7 Hz), 3.53 (t, 4H, J=5 Hz), 2.91 (q, 2H, J=7 Hz), 2.29 (t, 4H, J=5 Hz), 2.22 (t, 2H, J=7 Hz), 1.35 (s, 9H).
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;	3-(4-Morpholinyl)propan-1-amine (35.0 g, 243 mmol) was dissolved in tetrahydrofuran (THF, 250 mL), di-tert-butyl dicarbonate (58.0 g, 266 mmol) and N,N-diisopropylethylamine (DIPEA, 84 mL, 484 mmol) were added, and the solution was stirred overnight. The solvent was removed and the residue partitioned between ethyl acetate (EA) and 1.2M hydrochloric acid (300 mL). The pH was raised to 7 with saturated aqueous sodium bicarbonate and the layers separated. The aqueous layer was extracted twice with EA (150 mL each), and the EA layers were combined, washed with brine, and dried over magnesium sulfate. The solvent was removed, giving tert-butyl 3-(4-morpholinyl)propylcarbamate (39 g). Tent-butyl 3-(4-morpholinyl)propylcarbamate (3.5 g, 14.3 mmol) was dissolved in THF (30 mL), and sodium hydride (60% dispersion in mineral oil, 1.03 g, 25.8 mmol) was added in portions. After stirring for 5 min, ethyl iodide (13.4 g, 86.0 mmol) was added and the mixture was heated to 60 C. for 7 hr then stirred at room temperature overnight. Water (5 mL) was added and the solvent removed. The residue was dissolved in EA, and the solution was washed with brine, dried over magnesium sulfate, and the solvent removed to give crude tert-butyl ethyl[3-(4-morpholinyl)propyl]carbamate (2.5 g). Purification by silica gel chromatography eluting with 92:8 dichloromethane/methanol (DCM/MeOH) gave purified tert-butyl ethyl[3-(4-morpholinyl)propyl]carbamate (1.4 g). Purified tert-butyl ethyl[3-(4-morpholinyl)propyl]carbamate (350 mg, 1.3 mmol) was dissolved in 4.0M hydrogen chloride in dioxane (5 mL, 20 mmol) and stirred for 45 min. Water was added and the solution made basic with 2M aqueous sodium hydroxide. The product was extracted into EA, and the EA extract washed with brine and dried over magnesium sulfate. Removal of the EA gave N-ethyl-3-(4-morpholinyl)propan-1-amine (50 mg).

Reference： [1]Patent: US9301951,2016,B2 .Location in patent: Page/Page column 272; 273
[2]Patent: US2002/49191,2002,A1
[3]Patent: US2010/81653,2010,A1 .Location in patent: Page/Page column 9-10
[4]Organic Process Research and Development,2000,vol. 4,p. 488 - 497

43
[ 123-00-2 ]
[ 16588-16-2 ]
[ 310451-70-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In ethanol; at 60℃; for 12h;	A mixture of f-1 (0.022 mol), f-2 (0.066 mol) and NEt3 (0.066 mol) in C2H5OH (50 ml) was stirred at 60C for 12 hours, then evaporated to dryness and taken up in CH2Cl2. EPO <DP n="32"/>The organic layer was washed with H2O, dried (over MgSO4), filtered and the solvent was evaporated to dryness. Yield: 7.4 g of f-3 (100%).

Reference： [1]Patent: WO2006/97534,2006,A1 .Location in patent: Page/Page column 29-30

44
[ 123-00-2 ]
[ 63071-13-6 ]
C₁₃H₂₀ClN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		A mixture of <strong>[63071-13-6]4-chloro-2-pyridinecarboxaldehyde</strong> (200 mg, 0.0014 mol), N-(3- aminopropyl)morpholine (224 mg, 0.0015 mol), palphara-toluene sulfonic acid (134 mg, 0.00070 mol) and 3A molecular sieves was stirred at room temperature under Argon for 7 hours. Molecular sieves were filtered off, the reaction mixture was cooled down to O0C, and sodium borohydride (107 mg, 0.0028 mol) was slowly added. The mixture was stirred at room temperature for 17 hours, poured out into water and extracted with DCM. The organic layer was separated, washed with a saturated solution of hydrogen carbonate, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (40-63 mum) (eluent:DCM/MeOH/NuH3 85/15/3). The pure fractions were collected and the solvent was evaporated, yielding 230 mg (60%) of intermediate 76 as a yellow oil.

Reference： [1]Patent: WO2006/32631,2006,A1 .Location in patent: Page/Page column 61

45
[ 123-00-2 ]
[ 13852-51-2 ]
1-methyl-2-amino-N-(γ-morpholino propyl)-4-amino-5-nitro-benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In pyridine; (2S)-N-methyl-1-phenylpropan-2-amine hydrate;	EXAMPLE I Preparation of 1-methyl-2-amino-N-(gamma-morpholino propyl)-4-amino-5-nitro-benzene: The formula for the reaction is: STR10 1. The method of preparation: To 18.65 g (0.1 mole) of <strong>[13852-51-2]1-methyl-2-amino-4-chloro-5-nitro-benzene</strong> dissolved in 40 cc of pyridine, add drop by drop gamma-aminopropyl morpholine and heat it to reflux (130-135 C) for 10 hours. By distillation remove the pyridine in excess and introduce drop by drop the resulting oil obtained into 300 cc of 1N hydrochloric acid. This forms a chestnut colored precipitate which is washed twice with 80 cc of ice water. 23.5 g of a dry product are recovered which is recrystallized in a mixture of alcohol water. After drying, the product melts at 85 C.

Reference： [1]Patent: US4018556,1977,A

46
[ 123-00-2 ]
[ 857070-66-7 ]
[ 857070-67-8 ]

Yield	Reaction Conditions	Operation in experiment
82%		A mixture of b-3 (0.069 mol) and N-propylamino-morpholine (0.207 mol) was stirred at 125C for 4 hours, and then taken up in CH2C12/CH3OH. The organic layer was washed with a 10% solution OfK2CO3 in water, dried (over MgSO4), filtered and the solvent was evaporated until dryness. The residue (37 g) was purified by column chromatography over silica gel (eluent: CH2C12/CH3OH/NH4OH 90/10/0.5; 20-45mum). The pure fractions were collected and the solvent was evaporated, yielding 16.5g of intermediate b-4 (82%).

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 875 - 896
[2]Patent: WO2006/136562,2006,A1 .Location in patent: Page/Page column 23

47
[ 123-00-2 ]
[ 13544-44-0 ]
(2-chloro-5-iodopyrimidine-4-yl)-(3-morpholin-4-yl-propyl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -35 - 20℃; for 72h;	12) (2-chloro-5-iodopyrimidine-4-yl)-(3-morpholin-4-yl-propyl)-amine:; In accordance with procedure 2, 3-morpholin-4-yl-propylamine (0.73 ml, 5 mmol) and N-ethyldiisopropylamine (1.71 ml, 10 mmol) are dissolved in 100 ml acetonitrile under argon and cooled to -35C. The solution of 2,4-dichloro-5- iodo-pyrimidine (1.37, 5.0 mmol) in 50 ml acetonitrile is then added dropwise at-35C internal temperature. Stirred 1 hr further at -30 to -20 0C, then slowly warmed up to RT and stirred for 3 days at RT.The reaction mixture is concentrated on the rotary evaporator. The residue is treated with 200 ml ethyl acetate and 75 ml sat. NaHCO3 soln., well shaken and the aqueous phase further extracted 2 x with 75 ml portions of ethyl acetate. The ethyl acetate phase is dried over Na2SO4 dried, filtered, concentrated and the residue dried at the oil pump: 1.92 g colourless and crystalline crude product.The crude product is purified by column chromatography (5Og column, mobile phase: gradient hexane: ethyl acetate 80% to 100% ethyl acetate): 1.66 g(97%).1H-NMR (400 MHz, DMSO-D6): delta 1.66 (m, 2H), 2.30 (m, 6H), 3.37 (m, 2H), 3.57(m, 4H)1 7.42 (t, 1 H), 8.27 (s, 1 H).MS: 383 (MH+).
97%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -35 - 20℃; for 73h;	In accordance with procedure 2, 3-morpholin-4-yl-propylamine (0.73 ml, 5 mmol) and N-ethyldiisopropylamine (1.71 ml, 10 mmol) are dissolved in 100 ml acetonitrile under argon and cooled to -35 C. The solution of <strong>[13544-44-0]2,4-dichloro-5-iodo-pyrimidine</strong> (1.37, 5.0 mmol) in 50 ml acetonitrile is then added dropwise at -35 C. internal temperature. Stirred 1 hr further at -30 to -20 C., then slowly warmed up to RT and stirred for 3 days at RT. The reaction mixture is concentrated on the rotary evaporator. The residue is treated with 200 ml ethyl acetate and 75 ml sat. NaHCO3 soln., well shaken and the aqueous phase further extracted 2× with 75 ml portions of ethyl acetate. The ethyl acetate phase is dried over Na2SO4 dried, filtered, concentrated and the residue dried at the oil pump: 1.92 g colourless and crystalline crude product. The crude product is purified by column chromatography (50 g column, mobile phase: gradient hexane: ethyl acetate 80% to 100% ethyl acetate): 1.66 g (97%). 1H-NMR (400 MHz, DMSO-D6): delta 1.66 (m, 2H), 2.30 (m, 6H), 3.37 (m, 2H), 3.57 (m, 4H), 7.42 (t, 1H), 8.27 (s, 1H). MS: 383 (MH+).
97%	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -35 - 20℃; for 73h;	In accordance with GP 2, 3-morpholin-4-yl-propylamine (0.73 ml, 5 mmol) and N- ethyldiisopropylamine (1.71 ml, 10 mmol) were dissolved in 100 ml acetonitrile under argon and cooled to -35 C. The solution of <strong>[13544-44-0]2,4-dichloro-5-iodo-pyrimidine</strong> (1.37, 5.0 mmol) in 50 ml acetonitrile was then added dropwise at -35C internal temperature. Stirred 1 hr further at -30 to -20 C, then slowly warmed up to RT and stirred for 3 days at rt. The reaction mixture was concentrated on the rotary evaporator. The residue was treated with 200 ml ethyl acetate and 75 ml sat. NaHCO3 soln., well shaken and the aqueous phase further extracted 2 x with 75 ml portions of ethyl acetate. The ethyl acetate phase was dried over Na2SO4 dried, filtered, concentrated and the residue dried at the oil pump: 1.92 g colourless and crystalline crude product. The crude product was purified by column <n="119"/>chromatography (5Og column, mobile phase: gradient hexane: ethyl acetate 80% to 100% ethyl acetate): 1.66 g (97%).1H-NMR (400 MHz, DMSO-D6): 1.66 (m, 2H), 2.30 (m, 6H), 3.37 (m, 2H), 3.57 (m, 4H), 7.42 (t, 1 H), 8.27 (s, 1 H). MS: 383 (MH+).

Reference： [1]Patent: WO2007/71455,2007,A1 .Location in patent: Page/Page column 153
[2]Patent: US2007/232632,2007,A1 .Location in patent: Page/Page column 58-59
[3]Patent: WO2008/155140,2008,A1 .Location in patent: Page/Page column 117-118

48
[ 123-00-2 ]
[ 10320-42-0 ]
N-(3-morpholinopropyl)-5-nitropyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 70℃; for 20h;	<strong>[10320-42-0]<strong>[10320-42-0]2-Chloro-5-nitropyrimidin</strong>e</strong> 15 (500 mg, 3.13 mmol), 3-morpholinopropan-1-amine (1.35 g, 9.39 mmol) and DIEA (3.4 mL, 4.7 mmol) were taken up in IPA (20 mL) in a resealable pyrex tube and heated at 70° C. for 20 h. After cooling to rt, N-(3-morpholinopropyl)-5-nitropyrimidin-2-amine precipitated out of solution and was collected by filtration through a Buchner micro membrane, and washing with MeOH, then drying to afford the 5-nitro intermediate as a pale yellow solid.

Reference： [1]Journal of Medicinal Chemistry,2008,vol. 51,p. 1681 - 1694
[2]Patent: US2007/72862,2007,A1 .Location in patent: Page/Page column 27

49
[ 123-00-2 ]
[ 943329-45-1 ]
[4-(5-Methyl-3-phenyl-isoxazol-4-yl)-1-(4-nitro-phenyl)-1H-imidazol-2-ylmethyl]-(3-morpholin-4-yl-propyl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium iodide; In N,N-dimethyl-formamide; at 80℃; for 2h;	To a solution of 4-[2-chloromethyl-1-(4-nitro-phenyl)-1H-imidazol-4-yl]-5-methyl-3-phenyl-isoxazole (50 mg, 0.13 mmol) in DMF (2 mL) was added 4-(3-aminopropyl)morpholine (36.5 mg, 0.25 mmol) and KI (4.2 mg, 0.03 mmol) and the resulting mixture heated at 80 C. for 2 h. After cooling to room temperature, the mixture was then poured onto water and extracted with ethyl acetate. The combined organic layers were then washed with brine and water and then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, dichloromethane:methanol=100:0 to 80:20) afforded the title compound (47 mg, 74%) which was obtained as a yellow gum. MS: m/e=503.4 [M+H]+.

Reference： [1]Patent: US2007/161654,2007,A1 .Location in patent: Page/Page column 34

50
[ 123-00-2 ]
[ 40972-42-7 ]
[ 1034622-07-5 ]

Yield	Reaction Conditions	Operation in experiment
57%	In ethanol; at 120.0℃; for 16.0h;	6-Chloroimidazo[1,2-b]pyridazine 41 (6.53 mmol) was dissolved in chloroform (12 mL) and N-chlorosuccinimide (6.53 mmol) added under N2. After stirring for 16 h, the mixture was partitioned between saturated sodium hydrogensulfate solution (25 mL) and chloroform (12 mL). The organic layer was removed, washed with water (2×), dried and concentrated to provide <strong>[40972-42-7]3,6-dichloroimidazo[1,2-b]pyridazine</strong> 5 (1.05 g, 85%) as an orange solid; 1H NMR (500 MHz, CDCl3) delta 7.92 (d, J=9.5 Hz, 1H), 7.74 (s, 1H), 7.12 (d, J=9.5 Hz, 1H). 3,6-Dichloroimidazo[1,2-b]pyridazine 5 (150 mg, 0.8 mmol) and the desired amine (1 mL) were heated in a sealed tube for 16 hr at 120 C. Upon cooling the reaction mixture was concentrated and purified by column chromatography (12 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 80% methylene chloride over 30 min at 25 mL/min) to provide the desired product 6.

Reference： [1]Patent: US2008/153813,2008,A1 .Location in patent: Page/Page column 10

51
[ 7154-73-6 ]
[ 27578-60-5 ]
[ 140-31-8 ]
[ 2038-03-1 ]
[ 25560-00-3 ]
[ 123-00-2 ]
[ 5036-48-6 ]
[ 7663-77-6 ]
[ 34035-03-5 ]
[ 1761-71-3 ]
[ 6864-37-5 ]
[ 2213-43-6 ]
[ 63234-71-9 ]
[ 5906-35-4 ]
[ 59983-39-0 ]
[ 1664-40-0 ]
[ 6530-09-2 ]
[ 108-00-9 ]
[ 109-55-7 ]
[ 51387-90-7 ]
[ 102-83-0 ]
[ 849908-66-3 ]
C₁₅H₁₇ClN₂O [ No CAS ]
[ 849908-70-9 ]
[ 940358-24-7 ]
C₁₆H₁₉ClN₂O [ No CAS ]
C₁₉H₁₉ClN₂O [ No CAS ]
[ 849908-71-0 ]
C₁₇H₂₁ClN₂O₂ [ No CAS ]
[ 849908-67-4 ]
C₁₇H₂₁ClN₂O [ No CAS ]
[ 880815-24-7 ]
C₁₇H₂₂ClN₃O [ No CAS ]
C₁₈H₂₁ClN₂O [ No CAS ]
[ 849908-65-2 ]
[ 932172-19-5 ]
[ 875001-79-9 ]
[ 849908-68-5 ]
[ 849908-69-6 ]
[ 849908-81-2 ]
[ 849908-75-4 ]

Yield	Reaction Conditions	Operation in experiment
	With polymer-bound trimethyl ammonium cyanoborohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃; for 24 - 36h;Combinatorial reaction / High throughput screening (HTS);	All sixty diamines were separated in four groups based on their steric and electronic characteristics, Figures 1-4. Each diamine was measured in the amount of 0.05 g (approximately 0.3 mmol) and pooled together with the others in the group. Obtained diamine mixtures were dissolved in 5 ml of 1,2-dichloroethane and used for the syntheses. Each well of the 96-well filterplates was loaded with 0.2 ml of 1: 10 mixture of acetic acid: DCE, 0.03 ml of the diamine mixture in DCE (group 1, group 2, group 3, or group 4) to assure 0.04 mmol of the diamines per well, and shaken for 5 min at room temperature. Appropriate carbonyl compounds from the master plate (0.1 ml of 1.2 M solution) were added into corresponding wells of the reaction plates followed by the addition of (polystyrylmethyl) trimethylammonium cyanoborohydride, (0.020 g, 0.08 mmol per well). The reaction plates were sealed and placed on a shaker. The reaction was allowed to proceed 24-36 hours at room temperature. At the end, the reaction mixtures were filtered using a filtration manifold, and products were collected into four (one per group) collection plates. Solvents were evaporated in SpeedVac and formed residues were analyzed by mass spectrometry prior to biological screening. Mono and double alkylated products were observed in 1: 0.5 to 1: 2 ratios by mass spectral analysis.

Reference： [1]Patent: WO2005/34857,2005,A2 .Location in patent: Page/Page column 15; 22

52
[ 123-00-2 ]
[ 403-45-2 ]
[ 1221489-90-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 1659 - 1664

53
[ 123-00-2 ]
[ 1219482-39-9 ]
2-(5-[3-(4-morpholinyl)propyl]aminocarbonyl}-1H-benzimidazol-2(3H)-ylidene)-2-(4-trifluoromethylpyrimidin-2-yl)acetamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%		A mixture of 3,3-bis(methylthio)-2-(4-trifluoromethylpyrimidin-2-yl)acrylonitrile (682 mg, 2.34 mmol), 3,4-diaminobenzoic acid (392 mg, 2.57 mmol, 1.1 eq.), and 4-dimethylaminopyridine (143 mg, 1.17 mmol, 0.5 eq.) in ethanol (3 mL) was heated at 150 C. for 0.5 hr in a microwave. The mixture was cooled to room temperature, concentrated hydrochloric acid (1 mL) was added, and the mixture was allowed to stand for 0.5 hr. The precipitate that formed was collected by filtration, washed with ethanol and acetonitrile, and dried under vacuum to give 2-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(3-trifluoromethylpyrimidin-2-yl)acetonitrile (450 mg, 1.29 mmol, 55% yield) as a brown solid.The 2-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)-acetonitrile (450 mg, 1.29 mmol) from the previous step, dissolved in concentrated sulfuric acid (2 mL), was heated to 50 C. for 6 hr. The mixture was cooled to room temperature and added dropwise to rapidly stirred room-temperature water (500 mL). The precipitate that formed was collected by filtration, washed with water, and dried under vacuum to give 2-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (322 mg, 0.88 mmol, 68% yield) as a dark brown solid.To a room temperature solution of 2-[5-carboxy-1H-benzimidazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (630 mg, 1.73 mmol) in dimethylformamide (20 mL) was added DIPEA (661 muL, 3.79 mmol, 2.2 eq.), HBTU (720 mg, 1.90 mmol, 1.1 eq.). After 5 min, 3-(4-morpholinyl)propan-1-amine (277 muL, 1.90 mmol, 1.1 eq.) was added and the mixture was stirred at room temperature for 3 hr. The mixture was diluted with EA (50 mL) and washed three times with 5% aqueous sodium bicarbonate (50 mL each). The EA fraction was decanted, dried over magnesium sulfate, filtered, and concentrated under vacuum to give a yellow solid. About 2 mL of 4.0 M hydrogen chloride in dioxane was added, and the mixture was stirred for 15 min and then concentrated under vacuum to give 2-(5-[3-(4-morpholinyl)propyl]aminocarbonyl}-1H-benzimidazol-2(3H)-ylidene)-2-(4-trifluoromethylpyrimidin-2-yl)acetamide hydrochloride (750 mg, 1.52 mmol, 88% yield) as a yellow solid.

Reference： [1]Patent: US2010/81653,2010,A1 .Location in patent: Page/Page column 15-16

54
[ 123-00-2 ]
[ 1219482-38-8 ]
2-(6-[3-(morpholin-4-yl)propyl]aminocarbonyl}-benzothiazol-2(3H)-ylidene)-2-(4-trifluoromethyl-pyrimidin-2-yl)acetamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		A mixture of 4-amino-3-mercaptobenzoic acid (768 mg, 4.5 mmol), 3,3-bis(methylthio)-2-(4-trifluoromethylpyrimidin-2-yl)acrylonitrile (1.45 g, 5.0 mmol, 1.1 eq.), 4-dimethylaminopyridine (550 mg, 4.5 mmol, 1 eq.), and potassium carbonate (622 mg, 4.5 mmol, 1 eq.) in ethanol (20 mL) was heated at 160 C. for 0.4 hr in a microwave. The mixture was cooled to room temperature, diluted with DCM, and washed with 1M hydrochloric acid. The DCM fraction was decanted, filtered, and concentrated under vacuum to give 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethyl-pyrimidin-2-yl)acetonitrile (729 mg, 40% yield) as a brown solid.A solution of 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)-acetonitrile (620 mg, 1.70 mmol) in concentrated sulfuric acid (5 mL), was heated to 50 C. for 10 hr. The mixture was cooled to room temperature and added dropwise to rapidly stirred room-temperature water (100 mL). The precipitate that formed was collected by filtration, washed with water and hexanes, and dried under vacuum to give 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (587 mg, 90% yield) as a brown solid.To a room temperature solution of 2-[6-carboxybenzothiazol-2(3H)-ylidene]-2-(4-trifluoromethylpyrimidin-2-yl)acetamide (350 mg, 0.92 mmol) in acetonitrile (5 mL) was added triethylamine (250 muL, 1.79 mmol, 2 eq.), DEPBT (299 mg, 1.0 mmol, 1.1 eq.), and 3-(4-morpholinyl)-propan-1-amine (134 muL, 0.92 mmol, 1.0 eq.), and the mixture was stirred at room temperature until a yellow-brown precipitate formed. The precipitate was collected by filtration, washed with acetonitrile, and dried under vacuum to give a yellow solid. About 2 mL of 4.0 M hydrogen chloride in dioxane was added, and the mixture was stirred for 15 min and then concentrated under reduced pressure to give 2-(6-[3-(morpholin-4-yl)propyl]aminocarbonyl}-benzothiazol-2(3H)-ylidene)-2-(4-trifluoromethyl-pyrimidin-2-yl)acetamide hydrochloride (340 mg, 73% yield) as a yellow solid.

Reference： [1]Patent: US2010/81653,2010,A1 .Location in patent: Page/Page column 16

55
[ 123-00-2 ]
[ 1246635-45-9 ]
[ 1246635-46-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 2h;	Step 5: Synthesis of 2-(2-methoxypyridin-3-yl)-N-(3-morpholinopropyl)-1H-indole-5-carboxamide (5) To a solution of 2-(2-methoxypyridin-3-yl)-1H-indole-5-carboxylic acid (0.850 g, 0.317 mmol) in dimethylformamide (5 ml) was added HBTU (1.20 g, 0.317 mmol) and N,N-diisopropylethylamine (0.70 ml, 0.519 g, 0.402 mmol). The reaction mixture was allowed to stir for five minutes and 3-morpholinopropan-1-amine (0.59 ml) was added. The reaction was allowed to stir for 2 hours at room temperature. The reaction was quenched by adding water (25 ml), saturated sodium bicarbonate solution (25 ml) and extracted with EtOAc (2×50 ml). The organic extracts were combined, washed with brine (1×25 ml), dried over sodium sulfate and concentrated. The crude product was purified by flash column chromatography (SiO2, 100% EtOAc to 3% MeOH in EtOAc) to give the desired product as a white solid (1.09 g, 87%). M.p.=224-225 C.; 400 MHz 1H NMR (DMSO-d6) delta: 11.55 (s, 1H), 8.36 (t, J=5.4 Hz, 1H), 8.23 (dd, J=1.6 Hz, 7.6 Hz, 1H), 8.17 (dd, J=2.0 Hz, 5.2 Hz, 1H), 8.11 (s, 1H), 7.65 (dd, J=2 Hz, 8.4 Hz, 1H), 7.47 (d, J=8.4, 1H), 7.18-7.12 (m, 2H), 4.06 (s, 3H), 3.60-3.56 (m, 4H), 3.35-3.27 (m, 2H), 2.38-2.31 (m, 6H), 1.76-1.66 (m, 2H); LCMS: 395 [M+H].

Reference： [1]Patent: US2010/249127,2010,A1 .Location in patent: Page/Page column 54;56

56
[ 253801-04-6 ]
[ 123-00-2 ]
C₁₅H₂₀N₄O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1480 - 1483

57
[ 253801-04-6 ]
[ 123-00-2 ]
[ 1093303-38-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1480 - 1483

58
[ 123-00-2 ]
[ 1248477-79-3 ]

Yield	Reaction Conditions	Operation in experiment
	With imidazole-1-sulfonyl azide hydrochloride; copper(ll) sulfate pentahydrate; potassium carbonate; In methanol; at 20℃;	General procedure: Imidazole-1-sulfonyl azide hydrochloride (2.343 g, 11.21 mol) was added to the phenylmethanamine (1.0 g 9.345 mol), K2CO3 (2.57 g, 18.69 mol) and CuSO4.5H2O (2.5 mg, 10 mumol) in MeOH (5 mL) and the mixture stirred at room temperature for 6-16 h. Then filter through celite bed filtrate was evaporated gave the crude azide was used without purification for next step.

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 1693 - 1703
[2]Organic and Biomolecular Chemistry,2012,vol. 10,p. 5769 - 5773
[3]ACS Chemical Neuroscience,2015,vol. 6,p. 1317 - 1330
[4]Synthetic Communications,2020

59
[ 6820-95-7 ]
[ 123-00-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrazine hydrate; In ethanol; for 24h;Reflux;	General procedure: To a solution of compounds 6b-l (9.15 mmol) in 30 mLEtOH was added hydrazine monohydrate (36.6 mmol; 4 eq.) andthe mixture was vigorously stirred under reflux for 24 h. The whitesolid was filtered off and washed with EtOH. Filtrate was concentratedunder vacuum to dryness and taken up with EtOAc. The solidresidue was filtered again and filtrate was concentrated in vacuo toafford the desired products 7b-7l. NH2 signals are missing for allcompounds in 1H NMR spectra.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 304 - 317
[2]Journal of Medicinal Chemistry,2019,vol. 62,p. 9116 - 9140
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1593 - 1597
[4]ACS Chemical Neuroscience,2015,vol. 6,p. 1317 - 1330
[5]European Journal of Medicinal Chemistry,2016,vol. 109,p. 124 - 133

60
[ 123-00-2 ]
[ 1810-71-5 ]
[ 1366131-67-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 130℃; for 16h;	A solution of 6-bromo-2-chloroquinoline (100 mg, 0.412 mmol), [3-(4- morpholinyl)propyl]amine (178 mg, 1 .237 mmol) and DIPEA (216 muIota, 1.237 mmol) in N-Methyl-2- pyrrolidone (NMP) was maintained at 130C for 16 hours. The solution was cooled, poured into water and extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate, filtered, taken to a residue under reduced pressure and purified by columnchromatography to afford intermediate 6-bromo-N-[3-(4-morpholinyl)propyl]-2-quinolinamine (120 mg, 0.343 mmol, 83 % yield) as a white solid. A solution of 6-bromo-N-[3-(4- morpholinyl)propyl]-2-quinolinamine (120 mg, 0.343 mmol), 2,4-difluoro-N-[2-(methyloxy)-5- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-3-pyridinyl]benzenesulfonamide (197 mg, 0.463 mmol), Pd(Ph3P)4 (39.6 mg, 0.034 mmol) and potassium carbonate (142 mg, 1.028 mmol) in 1 ,4-dioxane (2 ml_)/Water (2.0 ml.) was maintained at 80C for 2 hours. The mixture was cooled, poured into ethyl acetate and washed with water. The organic layer was separated, dried over sodium sulfate, filtered and taken to a residue under reduced pressure to afford 2,4- difluoro-N-[2-(methyloxy)-5-(2-[3-(4-morpholinyl)propyl]amino}-6-quinolinyl)-3- pyridinyl]benzenesulfonamide (72 mg, 36.9 % yield) as a white solid following column chromatography. 1 H NMR (DMSO-d6) delta: 10.24 (br. s., 1 H), 8.34 (d, J = 2.3 Hz, 1 H), 7.87 - 7.92 (m, 2H), 7.85 (d, J = 2.0 Hz, 1 H), 7.74 - 7.80 (m, 1 H), 7.72 (dd, J = 8.9, 2.2 Hz, 1 H), 7.50 - 7.61 (m, 2H), 7.18 - 7.25 (m, 1 H), 7.15 (t, J = 5.3 Hz, 1 H), 6.79 (d, J = 9.0 Hz, 1 H), 3.64 (s, 3H), 3.56 - 3.63 (m, 4H), 3.39 - 3.47 (m, 2H), 2.35 - 2.47 (m, 6H), 1 .77 (quin, J = 7.0 Hz, 2H). LCMS (m/z, ES+) = 570 (M+H).

Reference： [1]Patent: WO2012/37108,2012,A1 .Location in patent: Page/Page column 210

61
[ 123-00-2 ]
[ 1392113-11-9 ]
[ 1392113-13-1 ]

Yield	Reaction Conditions	Operation in experiment
56.8%		Preparation of tert-butyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)- 5a,5b,8,8,l la-pentamethyl-3a-((3-morpholinopropylamino)methyl)-l-(prop-l-en-2- yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate.To a solution of ter/-butyl 4-((lR,3aS,5aR,5bR,7aR,l laS,l lbR,13aR,13bR)-3a- formyl-5a,5b,8,8,l la-pentamethyl-l-(prop-l-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,l l,l la,l lb,12,13,13a,13b-octadecahydro-lH- cyclopenta[a]chrysen-9-yl)benzoate (0.1 g, 0.167 mmol) in DCE (2 ml) was added acetic acid (1M in DCM) (0.167 ml, 0.167 mmol) and N-(3-Aminopropyl)morpholine (0.029 ml, 0.200 mmol). The mixture was stirred for 15 minutes at rt and sodium triacetoxyborohydride (0.071 g, 0.334 mmol) was added. The mixture was stirred at rt for 1.5 h and an additional 0.1 g of sodium triacetoxyborohydride was added. The mixture was stirred overnight at rt then was quenched with 7 ml of sat. NaHC(¾. The mixture was extracted with dichloromethane (3 x 7 ml) and the combined organic layers were dried with a2S04. The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure. The mixture was purified by flash chromatography using a 0-10% MeOH in dichloromethane gradient. The fractions containing the expected product were combined and concentrated under reduced pressure to give the title compound as a white foam (69 mg, 0.095 mmol, 56.8 % yield). LCMS: m/e 727.5 (M+H)+, 2.81 min (method 6).
		General procedure: A suspension oftert-butyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-formyl-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoate5(1 eq.), the corresponding amine (2 eq.) and acetic acid (2 - 5 eq.) in DCE (2 ml) was stirred at RT for 30 min.To this suspension was added sodium triacetoxyborohydride (5 eq.).The resulted mixture was stirred at RT for 18 - 72 hrs.The reaction mixture was diluted with 5 ml of saturated sodium carbonate and extracted with DCM (3 x 10 ml).The combined organic layers were dried over sodium sulfate, filtered and concentratedinvacuo.The crude product was purified by Biotage flash chromatography or was used directly in the next step without further purification.

Reference： [1]Patent: WO2012/106188,2012,A1 .Location in patent: Page/Page column 64-65
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 1550 - 1557

62
[ 123-00-2 ]
[ 459-80-3 ]
[ 1394833-66-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	General procedure: In a 50 mL two necked round flask were placed at room temperature under argon geranic acid 1 (250 mg, 1.5 × 10-3 mol) and 1,2-ethylenediamine (90 mg, 1.5 × 10-3 mol) in anhydrous CH2Cl2 (15 mL). The mixture was placed under stirring and diisopropylethylamine (195 muL, 1.5 × 10-3 mol) was slowly added, followed by the addition of the coupling reagent (BOP) (780 mug, 1.5 × 10-3 mol) dissolved in 5 mL of anhydrous CH2Cl2. The reaction was stirred for 12 h at 20 C. After removal of the solvents, the crude residue was purified by chromatography on a silicagel column using CH2Cl2/MeOH/NH4OH (7:3:1) eluent affording the expected coupling product 3 in 75% yield.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1174 - 1179

63
[ 123-00-2 ]
[ 1204601-62-6 ]
[ 1422642-77-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 170℃; for 3h;	General procedure: A mixture of 2 (0.6 mmol), amine (0.7 mmol), K2CO3 (1.2 mmol), and Pd(PPh3)4 (0.05 mmol) was heated in 10 ml DMF for 3 h at 170 C. The residue was purified by column chromatography on silica gel to afford the product.

Reference： [1]Tetrahedron,2013,vol. 69,p. 2309 - 2318

64
[ 123-00-2 ]
[ 41972-62-7 ]
[ 530-62-1 ]
[ 1426152-57-9 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 2110 - 2124

65
[ 123-00-2 ]
[ 1380432-31-4 ]
[ 1380432-32-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	With N-ethyl-N,N-diisopropylamine; In iso-butanol; at 120℃; for 0.5h;Microwave irradiation;	4Synthesis of EHop-016 [0031] 1H and 13C NMR spectra were recorded on a Bruker 400 MHz Spectrometer. Mass spectra were obtained on a Hewlett Packard 6890N GC/MS Spectrometer. All chemicals were purchased from Sigma Aldrich Chemical Company. The synthesis of EHop-016 (5) was performed in two steps according to the reaction scheme provided in FIG. 1(A), and carried out analogous to the procedure described in (58). (2-Chloro-pyrimidin-4-yl)-(9-ethyl-9H-carbazol-3-yl)-amine 3 was obtained as a pure compound in a yield of 53%. The product was identified with TLC, NMR and GC/MS. Rf=0.23 (3:1, Hexane-Ethyl Acetate); 1H NMR (DMSO-d6, 400 MHz) delta 1.32 (t, J=6.9 Hz, 3H), 4.45 (q, J=6.6 Hz, 2H), 6.72 (s, 1H), 7.20 (t, J=7.36 Hz, 1H), 7.47 (t, J=7.30 Hz, 1H), 7.56 (s, 1H), 7.62 (t, J=8.68 Hz, 1H), 8.11 (t, J=7.36 Hz, 1H), 8.27 (s, 1H), 10.1 (s, 1H); 13C (DMSO-d6, 100 MHz) delta 13.7, 37.0, 109.2, 109.4, 115.0, 118.7, 120.3, 121.3, 121.9, 122.3, 125.9, 129.9, 136.9, 140.0, 156.9, 159.6, 162.4; LRGC-MS m/z (rel %):[M]+ 276 (100), [M-Cl]+ 241 (40), [M-C5H5N3Cl]+ 134 (26). N4-(9-Ethyl-9H-carbazol-3-yl)-N2-(3-morpholin-4-yl-propyl)-pyrimidine-2,4-diamine 5 (EHop-016) was obtained as a pure compound in a yield of 93%. The product was identified to be essentially pure by TLC and NMR: Rf=0.34 (9:1, CH2Cl2-MeOH); 1H NMR (DMSO-d6, 400 MHz) delta 1.31 (t, J=7.0 Hz, 3H), 1.73 (m, 2H), 2.32 (m, 2H), 2.34 (t, J=6.89 Hz, 8H), 3.52 (m, 2H), 4.42 (q, J=7.0 Hz, 2H), 5.98 (d, J=5.7 Hz, 1H), 6.69 (t, J=5.3 Hz, 1H), 7.16 (t, J=7.4, 1H), 7.43 (t, J=7.2 Hz, 1H), 7.53 (t, J=9.0 Hz, 4H), 7.81 (d, J=5.4 Hz, 1H), 8.10 (s, 1H), 8.66 (s, 1H), 9.1 (s, 1H); 13C (DMSO-d6, 100 MHz) delta 13.7, 26.2, 36.9, 53.4, 56.3, 66.2, 108.9, 109.0, 118.2, 119.7, 120.2, 122.0, 122.2, 125.6, 132.5, 135.5, 139.9, 159.8, 160.9, 162.1.
52.1%	With caesium carbonate; In 1,4-dioxane; at 120 - 160℃;	For the synthesis of EHop-016 derivatives with modifications in building block C, an optimized procedure for the synthesis of EHop-016 was utilized (see U.S. Pat. No. 8,884,006, herein incorporated in its entirety). FIG. 11A describes Scheme 1B, a two-step synthetic procedure for the synthesis of EHop-016 and derivatives. The two-step synthetic scheme starts in ?step a? with the synthesis of EHop-014 (3) from dichloropyrimidine (1) and 3-amino-9-ethyl-carbazole (2). In the optimized procedure, first dichloropyrimidine as obtained from the supplier, is purified by slurrying in ethyl acetate for one hour. Insoluble solids (hydrolyzed impurities) are filtered and the ethyl acetate is removed via rotary evaporation. Subsequently, purified 1 is reacted with carbazole 2 via reflux in tetrahydrofuran in the presence of 1.2 equivalents triethyl amine. Compared with the previous method, workup was simplified by addition of water and ethyl acetate, which led to the precipitation of 3. Filtration over a Buechner funnel provided compound 3 without column chromatography as essentially the single 4-substituted regioisomer in a yield of 52.1%. Reaction of product 3 with different amines representing building block C, in the presence of either cesium carbonate or triethylamine amine in dioxane or dimethyl sulfoxide under microwave heating at 120 to 160 C. (step b) provided the desired EHop-016 derivatives. A summary of the products synthesized, together with their yields is provided in Table 4.

Reference： [1]Patent: US2013/172552,2013,A1 .Location in patent: Paragraph 0031
[2]Patent: US2019/125746,2019,A1 .Location in patent: Paragraph 0258

66
[ 123-00-2 ]
[ 1454657-25-0 ]
[ 1454657-27-2 ]

Yield	Reaction Conditions	Operation in experiment
54%		Example 172 7-(3-[(3-isopropylphenyl)amino]carbonyl}phenyl)-N-(3-morpholin-4-ylpropyl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carboxamide To a mixture of 7-(3-[(3-isopropylphenyl)amino]carbonyl}phenyl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carboxylic acid (25 mg, 0.06 mmol), triethylamine (0.017 mL, 0.12 mmol), and catalytic DMAP in 1.1 mL 1,2-dichloroethane at rt was added propylphosphonic anhydride solution (50 wt % in EtOAc, 0.043 mL, 0.072 mmol). After 5 min at rt, 3-morpholinopropylamine (0.011 mL, 0.072 mmol) was added and the reaction stirred at rt for 1.5 hours. The reaction was partitioned between EtOAc and brine/aqueous NaHCO3 solution, the EtOAc layer washed with brine/aqueous NaHCO3 solution, dried with anhydrous Na2SO4 and rotary evaporated. This material was chromatographed eluting with CHCl3/MeOH to give the title compound as an off-white solid (17 mg, 54%). 1H NMR (CDCl3) delta: 8.50 (s, 1H), 8.48 (s, 1H), 7.83-7.92 (m, 2H), 7.54 (d, J=4.7 Hz, 2H), 7.46 (d, J=8.2 Hz, 1H), 7.34-7.41 (m, 1H), 7.20-7.33 (m, 2H), 7.13 (d, J=7.9 Hz, 1H), 7.03 (d, J=7.3 Hz, 1H), 4.50 (s, 2H), 3.52-3.63 (m, 8H), 3.23 (t, J=5.7 Hz, 2H), 2.87-2.98 (m, 1H), 2.56 (t, J=6.0 Hz, 2H), 2.47 (br. s., 4H), 1.75-1.85 (m, 2H), 1.27 (d, J=7.0 Hz, 6H)
54%		Example 172 7-(3-[(3-isopropylphenyl)amino]carbonyl}phenyl)-N-(3-morpholin-4-ylpropyl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carboxamide To a mixture of 7-(3-[(3-isopropylphenyl)amino]carbonyl}phenyl)-5,6,7,8-tetrahydro-2,7-naphthyridine-4-carboxylic acid (25 mg, 0.06 mmol), triethylamine (0.017 mL, 0.12 mmol), and catalytic DMAP in 1.1 mL 1,2-dichloroethane at rt was added propylphosphonic anhydride solution (50 wt % in EtOAc, 0.043 mL, 0.072 mmol). After 5 min at rt, 3-morpholinopropylamine (0.011 mL, 0.072 mmol) was added and the reaction stirred at rt for 1.5 hours. The reaction was partitioned between EtOAc and brine/aqueous NaHCO3 solution, the EtOAc layer washed with brine/aqueous NaHCO3 solution, dried with anhydrous Na2SO4 and rotary evaporated. This material was chromatographed eluting with CHCl3/MeOH to give the title compound as an off-white solid (17 mg, 54%). 1H NMR (CDCl3) delta: 8.50 (s, 1H), 8.48 (s, 1H), 7.83-7.92 (m, 2H), 7.54 (d, J=4.7 Hz, 2H), 7.46 (d, J=8.2 Hz, 1H), 7.34-7.41 (m, 1H), 7.20-7.33 (m, 2H), 7.13 (d, J=7.9 Hz, 1H), 7.03 (d, J=7.3 Hz, 1H), 4.50 (s, 2H), 3.52-3.63 (m, 8H), 3.23 (t, J=5.7 Hz, 2H), 2.87-2.98 (m, 1H), 2.56 (t, J=6.0 Hz, 2H), 2.47 (br. s., 4H), 1.75-1.85 (m, 2H), 1.27 (d, J=7.0 Hz, 6H)

Reference： [1]Patent: US2013/237538,2013,A1 .Location in patent: Paragraph 0465
[2]Patent: US2013/237537,2013,A1 .Location in patent: Paragraph 0449-0450

67
[ 123-00-2 ]
4-undec-1-ynyl-pyridine-2-carboxylic acid [ No CAS ]
N-(3-morpholinopropyl)-4-(undec-1-ynyl)picolinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; for 18h;Cooling with ice;	[00097] N-(3-morpholinopropyl)-4-(undec-l-ynyl)picolinamide (CYD-1-42). To a solution of CYD-1-10 (100 mg, 0.36 mmol), triethylamine (147 mg, 1.46 mmol) and 3- morpholinopropan-1 -amine (68.5 mg, 0.47 mmol) in 10 mL of CH2C12 was added HBTU (276 mg, 0.73 mmol) in an ice-water bath. The reaction mixture was stirred at room temperature for 18 hrs. TLC indicated that the starting material was gone, and a less polar product was produced. The reaction mixture was diluted with CH2C12, washed with water and brine, and dried with anhydrous Na2S04. The solvent was removed under vacuum to give an oil residue. The residue was purified by silica gel column; eluting with 2%> Et3N in EtOAc afforded CYD-1-42 (125.0 mg, 85%) as a colorless oil; 1H NMR (600 MHz, CDC13) delta 8.94 (s, 1H), 8.46 (d, 1H, J= 4.8 Hz), 8.14 (s, 1H), 7.35 (m, 1H), 3.79 (m, 4H), 3.57 (m, 2H), 2.48 (m, 8H), 1.80 (m, 2H), 1.61 (m, 2H), 1.44 (t, 2H, J = 7.2 Hz), 1.29 (m, 10H), 0.88 (t, 3H, J= 7.2 Hz).
85%	With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; In dichloromethane; at 20℃; for 18h;Cooling with ice;	To a solution of CYD-1-10 (100 mg, 0.36 mmol), triethylamine (147 mg, 1.46 mmol) and 3-morpholinopropan-1-amine (68.5 mg, 0.47 mmol) in 10 mL of CH2Cl2 was added HBTU (276 mg, 0.73 mmol) in an ice-water bath. The reaction mixture was stirred at room temperature for 18 hrs. TLC indicated that the starting material was gone, and a less polar product was produced. The reaction mixture was diluted with CH2Cl2, washed with water and brine, and dried with anhydrous Na2SO4. The solvent was removed under vacuum to give an oil residue. The residue was purified by silica gel column; eluting with 2% Et3N in EtOAc afforded CYD-1-42 (125.0 mg, 85%) as a colorless oil; 1H NMR (600 MHz, CDCl3) delta 8.94 (s, 1H), 8.46 (d, 1H, J=4.8 Hz), 8.14 (s, 1H), 7.35 (m, 1H), 3.79 (m, 4H), 3.57 (m, 2H), 2.48 (m, 8H), 1.80 (m, 2H), 1.61 (m, 2H), 1.44 (t, 2H, J=7.2 Hz), 1.29 (m, 10H), 0.88 (t, 3H, J=7.2 Hz).

Reference： [1]Patent: WO2013/86266,2013,A2 .Location in patent: Paragraph 00097
[2]Patent: US9533973,2017,B2 .Location in patent: Page/Page column 37-38

68
[ 123-00-2 ]
[ 5491-18-9 ]
[ 1541203-86-4 ]

Yield	Reaction Conditions	Operation in experiment
65%		To a solution of (S)-7 (2.28 g, 8.0 mmol) in DCM (60 mL), DEPBT (2.40 g, 8.0 mmol) and DIPEA (2.78 mL, 16.0 mmol) were added and reaction mixture was stirred at room temperature for 5 min. 3-Morpholinopropylamine 8c (1.17 mL, 8.0 mmol) was added to the reaction mixture and it was stirred at room temperature for 20 H. Mixture was quenched with H2O (60 mL) and organic layer was washed with brine (2x60 mL), dried over Na2SO4 filtered and evaporated. The residue was purified by flash column chromatography eluting with DCM : MeOH (95 : 5) to afford 2.12 g of the titled compound 9c as a white solid (65 %): mp 131-132 C; [alpha]D20+ 52.4 (c 1, MeOH); deltaH (400 MHz; CDCl3) 7.39-7.29 (10H, m), 7.14-7.13 (1H, m), 6.26 (1H, d, J = 5.7 Hz), 5.15 (1H, d, J = 6.0 Hz), 5.11-5.04 (2H, m), 3.63-3.56 (4H, m), 3.36-3.31 (2H, m), 2.33-2.22 (6H, m), 1.60-1.59 (2H,m); 13C NMR (300 MHz; CDCl3) 170.3, 156.5, 139.4, 137.1, 129.8, 129.3, 129.0, 128.9, 128.2, 67.8, 67.7, 59.7, 58.4, 54.5, 54.3, 40.6, 25.2; HR-MS [M + H]+ observed = 412.2243, calculated = 412.2231.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 510 - 514

69
[ 123-00-2 ]
[ 1602748-79-7 ]
[ 1602747-83-0 ]

Yield	Reaction Conditions	Operation in experiment
65%		General procedure: To a stirred solution of 4-((2-(2,6-dichlorobenzyl)-1H-benzo[d]imidazol-1-yl)methyl)benzoic acid 35 (1.0 equiv) in CH2Cl2 wasadded oxalyl chloride (2.0 equiv) dropwise at room temperature.After catalytic amount of DMF (0.2 equiv) was added, the reactionmixture was stirred for 2 h at room temperature. And then, thereaction mixture was concentrated in vacuo. To the resulting residuewas added a mixture of the desired substituted amine(1.2 equiv) and DIPEA (2.5 equiv) in THF. The reaction mixture wasstirred at room temperature for 16 h, concentrated in vacuo, andextracted with CH2Cl2 (3 x 30 mL). The organic layerwas dried overanhydrous Na2SO4, filtered, concentrated, and purified by columnchromatography on SiO2 (CH2Cl2/MeOH: 10/1).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 125,p. 1172 - 1192

70
[ 123-00-2 ]
[ 161885-45-6 ]
[ 325779-25-7 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; In chloroform; at 25℃;	General procedure: To a solution of 2-oxo-2H-chromene-3-carbonyl chloride 3 (2mmol) and DMAP (4-dimethylaminopyridine, 2mmol) in chloroform (30mL) at 10C was added dropwise substituted amines (3.0mmol) for 30min. The reaction mixture was stirred at room temperature for 2-3h and washed with 20mL H2O, 10mL 1% NaHCO3, respectively, then dried on anhydrous MgSO4. The solvent was removed in vacuo and the crude residue was purified by chromatography on SiO2 (acetone/petroleum, 4: 1, v/v) to give title compounds 4a-4t as a colorless solid. Compounds 1-3 were prepared according to references [14,17].

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 80,p. 278 - 284

71
[ 123-00-2 ]
[ 1173095-69-6 ]
[ 1611471-79-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With dmap; In chloroform; at 25℃;	General procedure: To a solution of 2-oxo-2H-chromene-3-carbonyl chloride 3 (2mmol) and DMAP (4-dimethylaminopyridine, 2mmol) in chloroform (30mL) at 10C was added dropwise substituted amines (3.0mmol) for 30min. The reaction mixture was stirred at room temperature for 2-3h and washed with 20mL H2O, 10mL 1% NaHCO3, respectively, then dried on anhydrous MgSO4. The solvent was removed in vacuo and the crude residue was purified by chromatography on SiO2 (acetone/petroleum, 4: 1, v/v) to give title compounds 4a-4t as a colorless solid. Compounds 1-3 were prepared according to references [14,17].

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 80,p. 278 - 284

72
[ 123-00-2 ]
[ 71942-48-8 ]
[ 325779-24-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With dmap; In chloroform; at 25℃;	General procedure: To a solution of 2-oxo-2H-chromene-3-carbonyl chloride 3 (2mmol) and DMAP (4-dimethylaminopyridine, 2mmol) in chloroform (30mL) at 10C was added dropwise substituted amines (3.0mmol) for 30min. The reaction mixture was stirred at room temperature for 2-3h and washed with 20mL H2O, 10mL 1% NaHCO3, respectively, then dried on anhydrous MgSO4. The solvent was removed in vacuo and the crude residue was purified by chromatography on SiO2 (acetone/petroleum, 4: 1, v/v) to give title compounds 4a-4t as a colorless solid. Compounds 1-3 were prepared according to references [14,17].

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 80,p. 278 - 284

73
[ 123-00-2 ]
[ 13292-22-3 ]
C₄₅H₆₃N₃O₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		General procedure: Rifaldehyde (290.0 mg, 0.4 mmol) was dissolved in 30 mL CH2Cl2 and after the addition of catalyst (0.2 mmol ZnCl2 or 0.02 mmol HCl/EtOH) respective mixtures were made with each of the following compounds taken separately: propargylamine, 3-azidopropylamine, 2-azidoethylamine, (1-(2-aminoethyl)piperidine, 1-(2-aminoethyl)pyrrolidine, N,N-dimethylethylenediamine, 1-(3-aminopropyl)-imidazole, 3-morpholinopropyl-amine, 4-aminobenzylpiperidine, 1-(3-aminopropyl)pyrrolidine or 3-(dimethylamino)-1-propylamine, 3-(diethylamino)propyl-amine) (0.41 mmol) in 5 mL of C2H5OH. The mixtures were stirred at 45 C for half an hour and after that a half of the solvent volume was distilled off. To the cooled reaction mixture (room temperature) the reductant NaBH4 (6.8 mg, 0.18 mmol) was added portionwise over 1 min. The reaction mixture was evaporated to dryness, dissolved in 50 mL of ethyl acetate and extracted twice with 50 mL of water and brine. The separated organic layer was evaporated and synthesised derivatives of <strong>[13292-22-3]<strong>[13292-22-3]3-formylrifamycin</strong> SV</strong> (compounds 1-12) were then purified by column chromatography with silica gel (25 cm×1 cm, silica gel 60, 0.040-0.063 mm/230-400 mesh ASTM, Fluka) and ethyl acetate/methanol was applied as eluent (from 100:0 to 15:1).

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 84,p. 651 - 676

74
[ 123-00-2 ]
[ 14541-93-6 ]
N-(3-morpholinopropyl)-6-nitrobenzo[d]oxazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		A solution of 6-nitrobenzo[d]oxazole-2-thiol (KR-200) (13.61 mmol, 2.67 g)in dichloromethane (454 mL) and oxalyl chloride (17.01 mmol, 1.46 mL) wasplaced under argon atmosphere and cooled to 0 ?C. Dimethylformamide (15 mL) was added drop wise over a period of 45 minutes. CAUTION: The addition of dimethylformamide should be conducted slowly to avoid rapid evolution of gas. The reaction was stirred for 30 minutes at 0 ?C, then ice bath was removed and the reaction was allowed to warm to room temperature. After two hours, the reaction was again cooled to 0 ?C and triethylamine (40.83 mmol, 5.69 mL) was added drop wise over a period of 25 minutes. Then 3-morpholinopropan-1-amine (KR-347) (14.97 mmol, 2.16 g) was added, and the ice bath was removed. The reaction was stirred for twenty hours at room temperature then concentrated in vacuo yielding an orange solid. Silica gel column chromatography of the solid (20:1 dichloromethane/methanol) provided pure KR-202347 as a yellow powder in a 70% yield.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 3521 - 3525

75
[ 123-00-2 ]
[ 3328-69-6 ]
[ 1257525-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	for 2h;Reflux;	4-(3-Aminopropyl)morpholine (0.115 g, 0.8 mmol) was added to methanolic solution (20 mL) of DFP (0.065 g, 0.4 mmol) and the resulting solution was stirring for 15 min and then refluxed for 2 h. This ?solution of HL2? was used for subsequent reactions without isolation and further purification or characterization.

Reference： [1]Journal of Molecular Structure,2015,vol. 1101,p. 1 - 7

76
[ 123-00-2 ]
[ 3328-69-6 ]
C₂₃H₃₅Cl₂Cu₂N₇O₃ [ No CAS ]

Reference： [1]Journal of Molecular Structure,2015,vol. 1101,p. 1 - 7

77
[ 123-00-2 ]
[ 50-00-0 ]
[ 520-33-2 ]
C₂₄H₃₀N₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	In methanol; water; for 0.5h;	General procedure: To a solution of <strong>[520-33-2]hesperetin</strong> 2 (1.82mmol) in MeOH (40mL) was added 37% formaldehyde-water (150muL, 1.82mmol, 1.0equiv), after vigorous stirring at 30C for 30min, different amines (2.00mmol, 1.1equiv) were added and the mixture was stirred overnight. The reaction was monitored by TLC. The mixture was concentrated in vacuo and the residue was purified by silica gel column chromatography (CH2Cl2/MeOH, 5:1?3:1) to give title compounds 3a-3p (yields 47-80%, Scheme 1).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1460 - 1465

78
[ 123-00-2 ]
[ 10132-07-7 ]
C₁₁H₁₈ClN₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine; In butan-1-ol; at 90℃; for 12h;	General procedure: A mixture of 2-amino-4,6-dichloropyrimidine (1) (5 g, 30.5 mmol), the appropriate amine 2a or 2b (33.5 mmol), and triethylamine (152 mmol) in 150 mL n-butanol was heated to 90 C for 12 h. After cooling, the solvent was removed in vacuo, and the residue was partitioned between saturated aqueous Na2CO3 solution and ethyl acetate. The ethyl acetate layer was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography using the suitable mobile phase to afford the corresponding compounds 2a or 2b.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1301 - 1304

79
[ 123-00-2 ]
[ 4506-66-5 ]
N1,N2,N4,N5-tetrakis (3-morpholinopropyl)-2,5-diamino-1,4-benzoquinonediimine [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5340 - 5343

80
[ 123-00-2 ]
[ 53590-49-1 ]
1-[(5-chloro)-1H-indol-2-yl]-N-[3-(4-morpholinyl)propyl]methanamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: A round-bottom flask containing the 1H-indole-2-carbaldehyde34or <strong>[53590-49-1]5-chloro-1H-indole-2-carbaldehyde</strong>35 (1 eq.), the desiredamine (1 eq.) and anhydrous Na2SO4 (6 eq.) in CH2Cl2 was stirredovernight at room temperature. The reaction was filtered and thesolvent removed under reduced pressure. The residue was solubilizedin anhydrous MeOH and 2 eq. of NaBH4 were added in an icebath. After the addition, the ice bath was removed and the reactionwas kept under magnetic stirring at room temperature until thecompletion of the reaction was detected by TLC (1-2 h). The reactionwas quenched with distilled water, the MeOH was removedunder reduced pressure and the resulting aqueous phase wasextracted with 2 15 mL AcOEt. The organic layers were combinedand extracted with a 0.3 M HCl solution and the aqueouslayer was collected, alkalinized with 1 M NaOH and extracted with2 15 mL AcOEt. Finally, the organic layer was dried with Na2SO4,filtered and the solvent evapored under reduced pressure

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 1889 - 1900

81
[ 123-00-2 ]
[ 29427-58-5 ]
C₈H₁₈N₄O*(x)H₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	In water; at 100℃; for 24h;	General procedure: To a solution of primary amines 7a-l (2 eq) inwater (0.5 mol/L) wasadded O-methylisourea bisulfate (1 eq). Solution was stirred at 100 C for 24 h. After concentration to dryness, ethanol was addedand the residue was sonicated until apparition of a precipitate. Insome difficult cases, the suspension in ethanol was stored overnightin a freezer and triturated with cold ethanol to get a powder.Addition of a few drops of diethylether was also occasionallyneeded to induce precipitation. The solids 8a-l were collected byfiltration, washed with ethanol and dried overnight under vacuum.Due to the hygroscopicity of isolated solids, no melting points weredetermined for these series. NH signals are missing for all compoundsin 1H NMR spectra.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 304 - 317

82
[ 123-00-2 ]
[ 87486-34-8 ]
5-bromo-1-methyl-3-((3-morpholinopropyl)amino)pyrazin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 80℃; for 5h;	General procedure: To a solution of 2a-j (10 mmol, 1.0 eq) , <strong>[87486-34-8]3,5-dibromo-1-methylpyrazin-2(1H)-one</strong> (2.95 g, 11 mmol, 1.1 eq) and DIEA (3.3 mL,20 mmol, 2.0 eq) in MeCN (20mL) was stirred at 80 °C for 5 hours. After cooling to room temperature, thesolvent was removed in vacuo, and the residue was purified using silica gelchromatography to give the title compounds, yield 72-85percent.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1609 - 1613

83
[ 123-00-2 ]
[ 132388-68-2 ]
tert-butyl (S)-(1-((3-morpholinopropyl)amino)-1,4-dioxo-4-(tritylamino)butan-2-yl)carbamate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019

84
[ 123-00-2 ]
[ 101012-12-8 ]
N-(3-morpholinopropyl) 2-chlorothiazole-5-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 205 - 215

85
[ 123-00-2 ]
[ 5198-87-8 ]
N-(3-morpholinopropyl) 2-chlorothiazole-4-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019

86
[ 123-00-2 ]
[ 16865-11-5 ]
5,6-dichloro-N-(3-morpholinopropyl)-1H-benzo[d]imidazol-2-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019

87
[ 123-00-2 ]
[ 394-02-5 ]
C₁₄H₁₈FN₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In N,N-dimethyl-formamide; at 20℃;	General procedure: The synthetic pathways for the preparation of compounds 6h-m are depicted in Scheme S3. In a 25 mL round bottom flask, compound 7 (185 mg, 1 mmol) was dissolved in SOCl2 (6 mL) and heated to 50 C for 4-5 h. The progress of the reaction was monitored by TLC, and the reaction solution concentrated by rotary evaporation after completion of the reaction. The obtained acid chloride compound was dissolved in dry DMF, and diphenylmethanamine (8a, 219 mg, 1.2 mmol) and DMAP (61 mg, 0.5 mmol) were added, and the reaction was allowed to stand overnight. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed three times with saturated aqueous NaCl, and dried over anhydrous Na2SO4. N-Benzhydryl-5-fluoro-2-nitrobenzamide (9a), yield 72%.

Reference： [1]Bioorganic and medicinal chemistry letters,2020,vol. 30

88
[ 123-00-2 ]
[ 17326-27-1 ]
C₂₄H₃₆N₆O₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2020,vol. 63,p. 4849 - 4866

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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

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. 123-00-2 ] {[proInfo.proName]}

Quality Control of [ 123-00-2 ]

Related Doc. of [ 123-00-2 ]

Product Details of [ 123-00-2 ]

Calculated chemistry of [ 123-00-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 123-00-2 ]

Application In Synthesis of [ 123-00-2 ]

[ 123-00-2 ] Synthesis Path-Upstream 1~15

[ 123-00-2 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 123-00-2 ]

Amines

Related Parent Nucleus of [ 123-00-2 ]

Morpholines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 123-00-2 ]

Related Parent Nucleus of
[ 123-00-2 ]