[ CAS No. 123-00-2 ]

Name: 123-00-2|3-Morpholinopropan-1-amine|98%
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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 1~68

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

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

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

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

3
[ 123-00-2 ]
[ 14527-26-5 ]
[ 13910-60-6 ]

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

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

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

5
[ 123-00-2 ]
[ 6492-86-0 ]
[ 58232-30-7 ]

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

6
[ 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

7
[ 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

8
[ 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

9
[ 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

10
[ 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

11
[ 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

12
[ 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

13
[ 123-00-2 ]
[ 55447-00-2 ]
[ 200864-76-2 ]

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

14
[ 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

15
[ 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

16
[ 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

17
[ 123-00-2 ]
[ 108-77-0 ]
[ 14002-33-6 ]
C₈₃H₁₄₅N₃₃O₁₃ [ No CAS ]

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

18
[ 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

19
[ 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

20
[ 123-00-2 ]
[ 69812-29-9 ]
[ 16590-41-3 ]
C₃₃H₄₅N₅O₇S₂ [ No CAS ]

Reference： [1]Synlett,2002,p. 92 - 96

21
[ 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

22
[ 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

23
[ 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

24
[ 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

25
[ 123-00-2 ]
[ 83664-33-9 ]
[ 861884-74-4 ]

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

26
[ 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

27
[ 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

28
[ 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

29
[ 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

30
[ 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

31
[ 123-00-2 ]
[ 677297-51-7 ]
C₂₅H₂₇N₇O₃ [ No CAS ]

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

32
[ 123-00-2 ]
[ 677297-51-7 ]
C₃₂H₄₀N₈O₄ [ No CAS ]

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

33
[ 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

34
[ 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

35
[ 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

36
[ 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

37
[ 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

38
[ 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

39
[ 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

40
[ 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

41
[ 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

42
[ 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

43
[ 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

44
[ 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

45
[ 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

46
[ 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

47
[ 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

48
[ 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

49
[ 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

50
[ 123-00-2 ]
[ 403-45-2 ]
[ 1221489-90-2 ]

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

51
[ 253801-04-6 ]
[ 123-00-2 ]
C₁₅H₂₀N₄O [ No CAS ]

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

52
[ 253801-04-6 ]
[ 123-00-2 ]
[ 1093303-38-8 ]

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

53
[ 123-00-2 ]
[ 41972-62-7 ]
[ 530-62-1 ]
[ 1426152-57-9 ]

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

54
[ 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

55
[ 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

56
[ 123-00-2 ]
[ 3328-69-6 ]
C₂₃H₃₅Cl₂Cu₂N₇O₃ [ No CAS ]

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

57
[ 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

58
[ 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

59
[ 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

60
[ 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

61
[ 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

62
[ 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

63
[ 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

64
[ 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

65
[ 123-00-2 ]
[ 5198-87-8 ]
N-(3-morpholinopropyl) 2-chlorothiazole-4-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2019

66
[ 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

67
[ 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

68
[ 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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Code	Phrase
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P321
P322
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P342	If experiencing respiratory symptoms:
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P370	In case of fire:
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P372	Explosion risk in case of fire.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
P380	Evacuate area.
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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.
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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.
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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.
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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.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
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H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
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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 ]

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

[ 123-00-2 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 123-00-2 ]

Amines

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Morpholines

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[ 123-00-2 ]

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[ 123-00-2 ]