[ CAS No. 3160-91-6 ] {[proInfo.proName]}

Name: 3160-91-6|N-Carbamimidoylmorpholine-4-carboximidamide hydrochloride|98%
Brand: Ambeed
SKU: A148537
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Quality Control of [ 3160-91-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3160-91-6 ]

SDS Specification

Alternatived Products of [ 3160-91-6 ]

Product Details of [ 3160-91-6 ]

CAS No. :	3160-91-6	MDL No. :	MFCD00012798
Formula :	C₆H₁₄ClN₅O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FXYZDFSNBBOHTA-UHFFFAOYSA-N
M.W :	207.66	Pubchem ID :	76621
Synonyms :	ABOB hydrochloride;Moroxydine (hydrochloride);ABOB, Bimolin, Moroxydine free base, SKF 8898-A, SKF 8898A, Virugon, Virumin, Wirumin;ABOB;Moroxydine hydrochloride	Chemical Name :	N-Carbamimidoylmorpholine-4-carboximidamide hydrochloride

Calculated chemistry of [ 3160-91-6 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	3
Num. H-bond acceptors :	3.0
Num. H-bond donors :	4.0
Molar Refractivity :	56.39
TPSA :	98.22 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) :	-8.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.63
Log Po/w (WLOGP) :	-0.84
Log Po/w (MLOGP) :	-0.62
Log Po/w (SILICOS-IT) :	-1.12
Consensus Log Po/w :	-0.64

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.53
Solubility :	60.9 mg/ml ; 0.293 mol/l
Class :	Very soluble
Log S (Ali) :	-0.96
Solubility :	22.8 mg/ml ; 0.11 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.06
Solubility :	238.0 mg/ml ; 1.15 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.68

Safety of [ 3160-91-6 ]

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

Application In Synthesis of [ 3160-91-6 ]

* 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 [ 3160-91-6 ]
Downstream synthetic route of [ 3160-91-6 ]

[ 3160-91-6 ] Synthesis Path-Upstream 1~3

1
[ 127099-85-8 ]
[ 111-46-6 ]
[ 3160-91-6 ]

Yield	Reaction Conditions	Operation in experiment
5.2 kg	With sulfuric acid; ammonium chloride In water at 120℃; for 1 h; Sealed tube; Large scale	(1) to the 10L in the reactor with mechanical stirrer are sequentially added diethylene glycol 2.1 kg, dicy 2.0 kg, ammonium chloride 1.4 kg, quality quality concentration is 30percent sulfuric acid aqueous solution of 0.5 kg, the seal under stirring, every minutes to 3 degrees centigrade to the temperature increase speed of 120 °C, reactor pressure to rise to 0.3 MPa, reaction 1 hour later, natural cooling the reaction temperature to the room temperature, to obtain white milk;(2) the white cream is transferred to the 50L in glass autoclave, add 95percent ethanol 15 kg, heating reflux reaction 30 minutes to get mixed solution, the mixed fluid after filter drum heat filter in the crystallization kettle, the filtrate is cooled to room temperature in the crystallization kettle, separating white crystal, after centrifugal separation, the 80 °C after hot blast oven drying and under the conditions can be obtained trunk guanidine morpholine hydrochloride 5.2 kg, to dicy the idea receives rate to 81percent.

Reference： [1] Patent: CN105481797, 2016, A, . Location in patent: Paragraph 0039; 0040

2
[ 10024-89-2 ]
[ 127099-85-8 ]
[ 3160-91-6 ]

Yield	Reaction Conditions	Operation in experiment
17 kg	Stage #1: at 140℃; for 3 h; Large scale Stage #2: for 0.5 h; Reflux; Large scale	(3) The comparative experimental procedure (2) obtained in step morpholine hydrochloride was added to the 100L glass reactor, weighed 15Kg dicyandiamide was added to the reactor, the stirring reactor was heated to 140 , reactant in the molten state, the reaction was stirred for 3 hours, heating was stopped, cooled to room temperature.(4) The 40Kg95percent ethanol into a reactor, heated to reflux and stirred for 30 minutes, filtered hot and cooled to crystallize kettle crystallized white solid after centrifugation, oven dried by hot air to give a white morpholino amidine guanidine hydrochloride 17.0Kg ( morpholine total income was 48percent, in order to gauge their dicyandiamide 46percent yield).

Reference： [1] European Journal of Medicinal Chemistry, 1993, vol. 28, # 2, p. 149 - 158
[2] Polish Journal of Chemistry, 1991, vol. 65, # 5-6, p. 753 - 762
[3] Patent: CN105481797, 2016, A, . Location in patent: Paragraph 0056; 0057
[4] Molecules, 2018, vol. 23, # 7,

3
[ 110-91-8 ]
[ 127099-85-8 ]
[ 3160-91-6 ]

Reference： [1] Tetrahedron, 2013, vol. 69, # 19, p. 3867 - 3871

[ 3160-91-6 ] Synthesis Path-Downstream 1~88

1
[ 106-70-7 ]
[ 3160-91-6 ]
[ 66709-73-7 ]

Reference： [1]Patent: US2309663,1941,

2
[ 1004-36-0 ]
[ 3160-91-6 ]
[ 55558-88-8 ]

Reference： [1]European Journal of Medicinal Chemistry,1974,vol. 9,p. 255 - 258

3
[ 35196-48-6 ]
[ 3160-91-6 ]
[ 36739-65-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 611 - 613

4
[ 85-90-5 ]
[ 3160-91-6 ]
[ 52992-31-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1974,vol. 9,p. 14 - 18

5
[ 103-36-6 ]
[ 3160-91-6 ]
[ 30072-42-5 ]

Reference： [1]Journal of Medicinal Chemistry,1970,vol. 13,p. 1081 - 1089

6
[ 3131-64-4 ]
[ 3160-91-6 ]
[ 29936-03-6 ]

Reference： [1]Chimica Therapeutica,1970,vol. 5,p. 264 - 269

7
[ 1457-85-8 ]
[ 3160-91-6 ]
[ 7537-63-5 ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 611 - 613

8
[ 18522-98-0 ]
[ 3160-91-6 ]
[ 36802-73-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 611 - 613

9
[ 52872-85-2 ]
[ 3160-91-6 ]
[ 52872-87-4 ]
[ 52928-07-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1974,vol. 9,p. 14 - 18

10
[ 3160-91-6 ]
[ 874-60-2 ]
[ 43153-40-8 ]

Reference： [1]Farmaco, Edizione Scientifica,1973,vol. 28,p. 531 - 538

11
[ 3160-91-6 ]
[ 122-01-0 ]
[ 43210-57-7 ]

Reference： [1]Farmaco, Edizione Scientifica,1973,vol. 28,p. 531 - 538

12
[ 3160-91-6 ]
[ 100-07-2 ]
[ 43153-45-3 ]

Reference： [1]Farmaco, Edizione Scientifica,1973,vol. 28,p. 531 - 538

13
[ 3160-91-6 ]
[ 617-36-7 ]
[ 36739-62-5 ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 611 - 613

14
[ 3160-91-6 ]
[ 93-91-4 ]
[ 34747-60-9 ]

Reference： [1]Chemical and pharmaceutical bulletin,1971,vol. 19,p. 2284 - 2288

15
[ 3160-91-6 ]
[ 407-25-0 ]
4-morpholin-4-yl-6-trifluoromethyl-[1,3,5]triazin-2-ylamine [ No CAS ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1979,vol. 99,p. 387 - 392

16
[ 3160-91-6 ]
[ 623-20-1 ]
4-((E)-2-Furan-2-yl-vinyl)-6-morpholin-4-yl-[1,3,5]triazin-2-ylamine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1060 - 1065
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1250 - 1256

17
[ 93303-56-1 ]
[ 3160-91-6 ]
4-Morpholin-4-yl-6-[(E)-2-(5-nitro-furan-2-yl)-vinyl]-[1,3,5]triazin-2-ylamine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1060 - 1065
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1250 - 1256

18
[ 614-99-3 ]
[ 3160-91-6 ]
4-Furan-2-yl-6-morpholin-4-yl-[1,3,5]triazin-2-ylamine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,1992,vol. 28,p. 1060 - 1065
Khimiya Geterotsiklicheskikh Soedinenii,1992,p. 1250 - 1256

19
[ 10024-89-2 ]
[ 127099-85-8 ]
[ 3160-91-6 ]

Yield	Reaction Conditions	Operation in experiment
17 kg		(3) The comparative experimental procedure (2) obtained in step morpholine hydrochloride was added to the 100L glass reactor, weighed 15Kg dicyandiamide was added to the reactor, the stirring reactor was heated to 140 , reactant in the molten state, the reaction was stirred for 3 hours, heating was stopped, cooled to room temperature.(4) The 40Kg95percent ethanol into a reactor, heated to reflux and stirred for 30 minutes, filtered hot and cooled to crystallize kettle crystallized white solid after centrifugation, oven dried by hot air to give a white morpholino amidine guanidine hydrochloride 17.0Kg ( morpholine total income was 48percent, in order to gauge their dicyandiamide 46percent yield).
	In butan-1-ol; at 90 - 123℃; for 8h;	General procedure: Cyanoguanidine (dicyandiamide) (2.86 g, 34 mmol) was added to an appropriate solution of aminehydrochloride (34 mmol) in anhydrous n-butanol (10 mL). The mixture was carefully heated until theexothermic reaction was initiated (ca. 90 C) before being stirred at 122?123 C for 8 h. After cooling,the mixture was stirred for a further 6 h at room temperature. The next day, the precipitate was filtered,washed with n-butanol and isopropanol and purified by crystallization using methanol.

Reference： [1]European Journal of Medicinal Chemistry,1993,vol. 28,p. 149 - 158
[2]Polish Journal of Chemistry,1991,vol. 65,p. 753 - 762
[3]Patent: CN105481797,2016,A .Location in patent: Paragraph 0056; 0057
[4]Molecules,2018,vol. 23

Yield	Reaction Conditions	Operation in experiment
79.5%	In butan-1-ol; for 15h;Reflux;	General procedure: Example 108: Synthesis of N1-methyl biguanide hydrochloride (0246) (0247) Methylamine hydrochloride (1.3 g, 19.84 mmol) was dissolved in n-butanol (30 mL) at room temperature. Cyanoguanidine (1.68 g, 19.98 mmol) was added thereto and the mixture was stirred under reflux for 15 hours. The reaction mixture was concentrated under reduced pressure, and separated and purified using a chromatography in a condition where the ratio of methylene chloride to methyl alcohol was 9:1 and the target compound was obtained as a white solid (0.90 g, 61.0percent). 1H NMR (600 MHz, DMSO) delta2.86 (s, 3H) LCMS: 116.1 [M+H]+
		EXAMPLE 11 Synthesis of Moroxydine Amidinothiourea (2.36 g, 0.02 m) was suspended in 5 ml of water. Sodium molybdate dihydrate (0.012 g, 0.0005 m) and about 1.5 g of sodium chloride were added. The solution was cooled to 0° C. and 30percent hydrogen peroxide (8.4 ml, 0.08 m) was added dropwise: addition of the first 2.5 ml was very exothermic, dropwise addition required about 45 min. After addition of the second eq, the reaction mixture was allowed to warm to 14°-16° C., at which point the mixture exothermed to 50°-60° C. After cooling to 5° C., the third eq of peroxide was added dropwise; no exotherm was noted. Further cooling afforded a precipitate which was air dried and then placed under high vacuum to give 1.4 g, mp 158°-170° C.

21
[ 3160-91-6 ]
[ 24044-87-9 ]
4-(benzothiazol-2-ylsulfanylmethyl)-6-morpholin-4-yl-[1,3,5]triazin-2-ylamine [ No CAS ]

Reference： [1]Chemistry of Heterocyclic Compounds,2003,vol. 39,p. 632 - 639

22
diammonium hexabromoosmate(IV) [ No CAS ]
[ 3160-91-6 ]
{Os(C₄H₈ONC₂H₆N₅)3}⁽²⁺⁾*2Br^(1-)={Os(C₄H₈ONC₂H₆N₅)3}Br₂ [ No CAS ]

Reference： [1]Journal of the Less-Common Metals,1969,vol. 18,p. 117 - 122

23
iron(III) trichloride dihydrate [ No CAS ]
[ 3160-91-6 ]
[Fe(morpholinebiguanide)3]Cl₃*9H₂O [ No CAS ]

Reference： [1]Journal of Thermal Analysis and Calorimetry,2003,vol. 72,p. 489 - 495

24
heptapotassium tridecavanadomanganate(IV) octadecahydrate [ No CAS ]
[ 3160-91-6 ]
tripotassium(N-amidino-4-morpholincarboxamidine-H⁽¹⁺⁾)3[tridecavanadomanganate(IV)]*9(hydrate) [ No CAS ]

Reference： [1]Inorganic Chemistry Communications,2005,vol. 8,p. 433 - 436

25
[ 3160-91-6 ]
cobalt(II) nitrate [ No CAS ]
[CoCl₃(C₆H₁₄N₅O)] [ No CAS ]

Reference： [1]Russian Journal of Coordination Chemistry,1999,vol. 25,p. 537 - 542

26
zinc(II) perchlorate [ No CAS ]
[ 3160-91-6 ]
[ZnCl₃(C₆H₁₄N₅O)] [ No CAS ]

Reference： [1]Russian Journal of Coordination Chemistry,1999,vol. 25,p. 537 - 542

27
3,5-dinitro-1,2,4-cyclopentanetrione silver salt [ No CAS ]
[ 3160-91-6 ]
bis-moroxydine 3,5-dinitro-1,2,4-cyclopentanetrione [ No CAS ]

Reference： [1]Chemistry - A European Journal,2008,vol. 14,p. 5596 - 5603

28
3H⁽¹⁺⁾*(PMo₁₂O₄₀)^(3-)*20H₂O=H₃(PMo₁₂O₄₀)*20H₂O [ No CAS ]
[ 3160-91-6 ]
3(C₄H₈NO)C(NH)NHC(NH)NH₃⁽¹⁺⁾*PMo₁₂O₄₀^(3-)=[(C₄H₈NO)C(NH)NHC(NH)NH₃]3(PMo₁₂O₄₀) [ No CAS ]

Reference： [1]Russian Journal of Coordination Chemistry,2009,vol. 35,p. 195 - 199

29
3H⁽¹⁺⁾*(PMo₁₂O₄₀)^(3-)*20H₂O=H₃(PMo₁₂O₄₀)*20H₂O [ No CAS ]
[ 3160-91-6 ]
2(C₄H₈NO)C(NH)NHC(NH)NH₃⁽¹⁺⁾*H⁽¹⁺⁾*PMo₁₂O₄₀^(3-)*5H₂O=[(C₄H₈NO)C(NH)NHC(NH)NH₃]2(HPMo₁₂O₄₀)*5H₂O [ No CAS ]

Reference： [1]Russian Journal of Coordination Chemistry,2009,vol. 35,p. 195 - 199

30
[ 110-91-8 ]
[ 127099-85-8 ]
[ 3160-91-6 ]

Yield	Reaction Conditions	Operation in experiment
85%		(1) salt formation reaction, adding morpholine to the reactor, stirring and bringing the temperature to 29 C, and then adding concentrated hydrochloric acid;When the pH value in the reactor is 1 to 2 and is constant, the dropwise addition is stopped. After the reaction is completed, the water is concentrated in a vacuum to obtain morpholine hydrochloride having a water content of 5% or less; morpholine and concentrated hydrochloric acid are obtained. The molar ratio is 1:1.15;(2) addition reaction, adding isoamyl alcohol and dicyandiamide to the above morpholine hydrochloride, and increasing the temperature to 135 C to start the addition reaction; after the reaction starts, the reactor is first dissolved, then turbid, turbid After the reaction was continued for 3 h, the reaction was completed; then it was cooled to room temperature, stirred for 0.5 h, filtered, and the filter cake was washed with isoamyl alcohol, and dried to obtain a crude morpholine hydrochloride having a morpholine yield of 95%; morpholine and double The molar ratio of cyanamide is 1:1.15;(3) Purification, referring to Example 1, a morpholinium hydrochloride fine product having a morpholine yield of 85% was obtained.

Reference： [1]Patent: CN110016004,2019,A .Location in patent: Paragraph 0024-0030
[2]Tetrahedron,2013,vol. 69,p. 3867 - 3871

31
[ 3160-91-6 ]
[ 1430334-11-4 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

32
[ 3160-91-6 ]
[ 1430334-12-5 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

33
[ 3160-91-6 ]
[ 1430334-13-6 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

34
[ 3160-91-6 ]
[ 1430334-14-7 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

35
[ 3160-91-6 ]
[ 1430334-15-8 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

36
[ 3160-91-6 ]
[ 1430334-16-9 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

37
[ 3160-91-6 ]
[ 1430334-17-0 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

38
[ 3160-91-6 ]
[ 1430334-18-1 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

39
[ 3160-91-6 ]
[ 1430334-19-2 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

40
[ 3160-91-6 ]
[ 1430334-20-5 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

41
[ 3160-91-6 ]
[ 1430334-21-6 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

42
[ 124-41-4 ]
[ 3160-91-6 ]
[ 141-78-6 ]
[ 5122-64-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	In tetrahydrofuran; at 70℃; for 0.333333h;Microwave irradiation;	General procedure: A mixture of sodium methoxide (1.5 mmol) prepared from Na and methanol, arylbiguanide hydrochloride (1 mmol) 1 and ester (3 mmol) in dry THF (5 mL) was introduced into a round-bottomed flask equipped with a condenser and a magnetic stirring bar. The flask was placed in the microwave cavity and exposed to microwave irradiation for 20 min at 70 C using irradiation power of 100W. On cooling to room temperature, the mixture was evaporated under vacuum, and the residue was subjected to flash chromatography (silica gel, 5percent methanol/CH2Cl2) to afford the desired product as a white solid.

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

43
[ 94-08-6 ]
[ 124-41-4 ]
[ 3160-91-6 ]
[ 43153-40-8 ]

Yield	Reaction Conditions	Operation in experiment
72.5%	In tetrahydrofuran; at 70℃; for 0.333333h;Microwave irradiation;	General procedure: A mixture of sodium methoxide (1.5 mmol) prepared from Na and methanol, arylbiguanide hydrochloride (1 mmol) 1 and ester (3 mmol) in dry THF (5 mL) was introduced into a round-bottomed flask equipped with a condenser and a magnetic stirring bar. The flask was placed in the microwave cavity and exposed to microwave irradiation for 20 min at 70 C using irradiation power of 100W. On cooling to room temperature, the mixture was evaporated under vacuum, and the residue was subjected to flash chromatography (silica gel, 5percent methanol/CH2Cl2) to afford the desired product as a white solid.

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

44
[ 124-41-4 ]
[ 3160-91-6 ]
[ 101-97-3 ]
[ 1430334-09-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	In tetrahydrofuran; at 70℃; for 0.333333h;Microwave irradiation;	General procedure: A mixture of sodium methoxide (1.5 mmol) prepared from Na and methanol, arylbiguanide hydrochloride (1 mmol) 1 and ester (3 mmol) in dry THF (5 mL) was introduced into a round-bottomed flask equipped with a condenser and a magnetic stirring bar. The flask was placed in the microwave cavity and exposed to microwave irradiation for 20 min at 70 C using irradiation power of 100W. On cooling to room temperature, the mixture was evaporated under vacuum, and the residue was subjected to flash chromatography (silica gel, 5percent methanol/CH2Cl2) to afford the desired product as a white solid.

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

45
[ 124-41-4 ]
[ 3160-91-6 ]
[ 2045-25-2 ]

Yield	Reaction Conditions	Operation in experiment
98%	In tetrahydrofuran; at 70℃; for 0.333333h;Microwave irradiation;	General procedure: A mixture of sodium methoxide (1.5 mmol) prepared from Na and methanol, arylbiguanide hydrochloride (1 mmol) 1 and ester (3 mmol) in dry THF (5 mL) was introduced into a round-bottomed flask equipped with a condenser and a magnetic stirring bar. The flask was placed in the microwave cavity and exposed to microwave irradiation for 20 min at 70 C using irradiation power of 100W. On cooling to room temperature, the mixture was evaporated under vacuum, and the residue was subjected to flash chromatography (silica gel, 5percent methanol/CH2Cl2) to afford the desired product as a white solid.

Reference： [1]Tetrahedron,2013,vol. 69,p. 3867 - 3871

46
[ 3160-91-6 ]
[ 77295-59-1 ]
4-(4-chlorobenzyl)-6-morpholino-1,3,5-triazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With copper(l) iodide; glycine; In 1,4-dioxane; at 110℃; for 13h;	biguanide hydrochloride was added in a reaction vessel, piperidine (0 ·2057g), 1,1-dibromo (3,4-dimethoxyphenyl) styrene (0 · 1286g), cuprous iodide (0 · 0076g), 2, 2'- dipyridyl (0 · 0125g), potassium (0 · 5094g) phosphate, mixed at 110 °C in oil bath and stirred in 1,4-dioxane (5mL) for 13 hours; the reaction after filtration, the filter residue washed with methanol, the filtrate was concentrated by column chromatography (dichloromethane: methanol = 50: 1), R f value of 0.3 were collected ~ 035 eluate by distillation under reduced pressure, and dried to give. the target compound III-I (billion. l67g, yield 81percent).The procedure described in Example 1, except that piperidine hydrochloride was replaced with biguanide N, N, Nu ', Nu' - tetramethyl-biguanide hydrochloride (0. 1937g, 1.0 Ommol), 2, 2 '- bipyridine to glycine (0. 0060g, 0. 08mmol), to obtain the objective compound II1-5 (0 · 0546g, 43percent yield).[0051] 1H NMR (500MHz, CDCl3): delta 7. 07 (d, J = 1. 8Hz, 1H), 6. 94 (dd, J = 8. I, I. 8Hz, 1H), 6. 79 ( d, J = 8. 1Hz, 1H), 3. 88 (s, 3H), 3. 86 (s, 3H), 3. 76 (s, 2H), 3. 13 (s, I 2H) square

Reference： [1]Patent: CN105384702,2016,A .Location in patent: Paragraph 0020; 0057; 0058; 0059; 0060

47
[ 127099-85-8 ]
[ 111-46-6 ]
[ 3160-91-6 ]

Yield	Reaction Conditions	Operation in experiment
5.2 kg	With sulfuric acid; ammonium chloride; In water; at 120℃; under 2250.23 Torr; for 1h;Sealed tube; Large scale;	(1) to the 10L in the reactor with mechanical stirrer are sequentially added diethylene glycol 2.1 kg, dicy 2.0 kg, ammonium chloride 1.4 kg, quality quality concentration is 30percent sulfuric acid aqueous solution of 0.5 kg, the seal under stirring, every minutes to 3 degrees centigrade to the temperature increase speed of 120 °C, reactor pressure to rise to 0.3 MPa, reaction 1 hour later, natural cooling the reaction temperature to the room temperature, to obtain white milk;(2) the white cream is transferred to the 50L in glass autoclave, add 95percent ethanol 15 kg, heating reflux reaction 30 minutes to get mixed solution, the mixed fluid after filter drum heat filter in the crystallization kettle, the filtrate is cooled to room temperature in the crystallization kettle, separating white crystal, after centrifugal separation, the 80 °C after hot blast oven drying and under the conditions can be obtained trunk guanidine morpholine hydrochloride 5.2 kg, to dicy the idea receives rate to 81percent.

Reference： [1]Patent: CN105481797,2016,A .Location in patent: Paragraph 0039; 0040

48
[ 3160-91-6 ]
[ 100-51-6 ]
[ 35541-11-8 ]

Reference： [1]New Journal of Chemistry,2016,vol. 40,p. 8225 - 8228

49
[ 7436-90-0 ]
[ 3160-91-6 ]
[ 1430334-09-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With [2,2]bipyridinyl; copper(l) iodide; In 1,4-dioxane; at 110℃; for 13h;	To the reaction vessel was added morpholine biguanide hydrochloride (0.2077 g), 1,1-dibromo-styrene (0.1048 g), cuprous iodide(0.0076 g), 2,2'-bipyridine (0.0125 g) and potassium phosphate (0.5094 g) were mixed in 1,4-dioxane (5 mL)And the mixture was stirred for 13 hours in a bath. After completion of the reaction, the reaction mixture was filtered and the residue was washed with methanol. The filtrate was concentrated and purified by column chromatography (dichloromethane:Methanol = 50: 1), collecting Rf value of 0.3 ~ 0.35 of the eluent, vacuum distillation and drying to obtain the target compound (I), the amount of 0.0847g,The yield was 78percent.

Reference： [1]Patent: CN105503754,2016,A .Location in patent: Paragraph 0019; 0020; 0021

50
[ 3160-91-6 ]
[ 259886-50-5 ]
C₆H₁₃N₅O*ClH*C₄₂H₄₂N₂₈O₁₄ [ No CAS ]

Reference： [1]Journal of Inclusion Phenomena and Macrocyclic Chemistry,2017,vol. 87,p. 21 - 28

51
[ 3160-91-6 ]
[ 259886-51-6 ]
C₄₈H₄₈N₃₂O₁₆*C₆H₁₃N₅O*ClH [ No CAS ]