[ CAS No. 1937-19-5 ] {[proInfo.proName]}

Name: 1937-19-5|Aminoguanidine hydrochloride|98%
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Quality Control of [ 1937-19-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1937-19-5 ]

SDS Specification

Alternatived Products of [ 1937-19-5 ]

Product Details of [ 1937-19-5 ]

CAS No. :	1937-19-5	MDL No. :	MFCD00039074
Formula :	CH₇ClN₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UBDZFAGVPPMTIT-UHFFFAOYSA-N
M.W :	110.55	Pubchem ID :	2734687
Synonyms :	Pimagedine hydrochloride;GER-11;Guanylhydrazine hydrochloride;GER11. aminoguanidine. Pimagedine hydrochloride;MDL201228;YM-585;Pimagedine, MDL-201228;Aminoguanidine (hydrochloride);Monoaminoguanidine;Imino semicarbazide;Hydrazinecarboximidamide;Guanyl hydrazine;Pimagedine;Aminoguanidinium chloride;Aminoguanidine hydrochloride

Calculated chemistry of [ 1937-19-5 ]

Physicochemical Properties

Num. heavy atoms :	6
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	4.0
Molar Refractivity :	25.69
TPSA :	87.92 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) :	-7.61 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	-0.89
Log Po/w (WLOGP) :	-0.85
Log Po/w (MLOGP) :	-1.0
Log Po/w (SILICOS-IT) :	-1.01
Consensus Log Po/w :	-0.75

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.1
Solubility :	140.0 mg/ml ; 1.26 mol/l
Class :	Highly soluble
Log S (Ali) :	-0.47
Solubility :	37.1 mg/ml ; 0.336 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.83
Solubility :	742.0 mg/ml ; 6.71 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.68

Safety of [ 1937-19-5 ]

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

Application In Synthesis of [ 1937-19-5 ]

* 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 [ 1937-19-5 ]
Downstream synthetic route of [ 1937-19-5 ]

[ 1937-19-5 ] Synthesis Path-Upstream 1~5

1
[ 131543-46-9 ]
[ 1937-19-5 ]
[ 1120-99-6 ]

Reference： [1] ChemMedChem, 2016, p. 1778 - 1789

2
[ 2582-30-1 ]
[ 1937-19-5 ]

Reference： [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 26, p. 7897 - 7901
[2] Russian Journal of Applied Chemistry, 2008, vol. 81, # 10, p. 1813 - 1817
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8168 - 8172
[4] Organic and Biomolecular Chemistry, 2010, vol. 8, # 4, p. 873 - 880
[5] Chemistry - A European Journal, 2017, vol. 23, # 46, p. 11159 - 11168

3
[ 1309884-92-1 ]
[ 1937-19-5 ]
[ 64-19-7 ]

Reference： [1] Russian Journal of Applied Chemistry, 2011, vol. 84, # 3, p. 400 - 406

4
[ 102-52-3 ]
[ 1937-19-5 ]
[ 4023-02-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8168 - 8172

5
[ 878671-95-5 ]
[ 1937-19-5 ]
[ 878671-96-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 12 h;	The intermediate compound V (13.3mmol, 3.0g), aminoguanidine hydrochloride (26.6mmol, 2.9g) was added to 50mL of N, N-dimethyl formamide, was added under stirring N, N-diisopropylethylamine amine (39.9mmol, 5.1g), then the reaction 50 12h, the solvent was evaporated to dryness 20mL2M sodium hydroxide was added, and the reaction was continued 50 12h. After stopping the reaction, the reaction mixture was filtered, and the filtrate was washed with dilute hydrochloric acid to pH = 4, shows a large number of white precipitate was filtered, and then at a temperature of 45-50 dried under vacuum to give 2.85g the VI intermediate compound,(76percent)
49%	Stage #1: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 15 h; Stage #2: With sodium hydroxide In water at 50℃; for 60 h;	A mixture of aminoguanidine hydrochloride (3.18 g, 29 mmol), l-cyclopropyl-4- isothiocyanato-naphthalene (3.24 g, 14 mmol) and diisopropylethylamine (3 eq) in DMF (20 mL) was stirred at 50 0C for 15 hours. The solvent was evaporated, toluene was added, and the solvent was evaporated again. A 2.0 M aqueous solution of sodium hydroxide (30 mL) was added and the reaction mixture was heated at 50 0C for 60 hours. The reaction mixture was filtered, and the filtrate was neutralized with a 2.0 M aqueous solution of HCl. New filtration, then evaporation of solvent and purification of the residue by silica gel chromatography to yield 5-amino-4-(4-cyclopropylnaphthalen-l-yl)- 4H-[l,2,4]triazole-3-thiol (2.0 g, 49percent).
49%	Stage #1: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 50℃; for 15 h; Stage #2: at 50℃; for 60 h; Stage #3: With hydrogenchloride In water	STEP E: 5-Amino-4-(l-cyclopropylnaphthalen-4-yl)-4H-l,2,4-triazole-3- thiolA mixture of aminoguanidine hydrochloride (3.18 g, 29 mmol), l-cyclopropyl-4- isothiocyanato naphthalene (3.24 g, 14 mmol) and diisopropylethylamine (3 eq) in DMF (20 mL) was stirred at 50 °C for 15 hours. The solvent was removed under reduced pressure, toluene added, and the solvent was evaporated again. Sodium hydroxide solution (2M, 30 mL) was added and the reaction mixture heated at 50 °C for 60 hours. The reaction mixture was filtered and the filtrate neutralized with aqueous HCl (2M). The mixture was re-filtered and the solvent removed under reduced pressure. The residue was purified by silica gel chromatography to yield 5-amino-4-(l-cyclopropylnaphthalen-4-yl)-4H-l,2,4-triazole-3- thiol (2.0 g, 49percent).

Reference： [1] Patent: CN105566237, 2016, A, . Location in patent: Paragraph 0066; 0067; 0068
[2] Patent: WO2009/70740, 2009, A2, . Location in patent: Page/Page column 89-90
[3] Patent: WO2006/26356, 2006, A2, . Location in patent: Page/Page column 21
[4] Patent: WO2011/85009, 2011, A2, . Location in patent: Page/Page column 37

[ 1937-19-5 ] Synthesis Path-Downstream 1~88

1
[ 3722-80-3 ]
[ 1937-19-5 ]
[ 113950-41-7 ]

Reference： [1]Patent: DE943408,1953,

2
[ 24644-78-8 ]
[ 1937-19-5 ]
4-Methyl-indanon-1-amidinohydrazon [ No CAS ]

Reference： [1]Patent: FR2272653,1975,
Patent: DE2524114,1975,
Chem.Abstr.,1976,vol. 84

3
[ 15115-59-0 ]
[ 1937-19-5 ]
4-Chlorindanon-1-amidinohydrazon [ No CAS ]

Reference： [1]Patent: FR2272653,1975,
Patent: DE2524114,1975,
Chem.Abstr.,1976,vol. 84

4
[ 4593-38-8 ]
[ 1937-19-5 ]
5-Methyl-indan-1-on-amidinohydrazon [ No CAS ]

Reference： [1]Patent: FR2272653,1975,
Patent: DE2524114,1975,
Chem.Abstr.,1976,vol. 84

5
[ 39627-61-7 ]
[ 1937-19-5 ]
7-Methyl-indan-1-on-amidinohydrazon [ No CAS ]

Reference： [1]Patent: FR2272653,1975,
Patent: DE2524114,1975,
Chem.Abstr.,1976,vol. 84

6
[ 67901-82-0 ]
[ 1937-19-5 ]
C₁₁H₁₄N₄O [ No CAS ]

Reference： [1]Patent: FR2272653,1975,
Patent: DE2524114,1975,
Chem.Abstr.,1976,vol. 84

7
[ 69975-65-1 ]
[ 1937-19-5 ]
6-Amino-1-indanon-amidinohydrazon [ No CAS ]

Reference： [1]Patent: FR2272653,1975,
Patent: DE2524114,1975,
Chem.Abstr.,1976,vol. 84

8
[ 342-25-6 ]
[ 1937-19-5 ]
4,2'-Difluor-benzophenon-guanylhydrazon [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1969,vol. 12,p. 21 - 25

9
[ 3891-59-6 ]
[ 1937-19-5 ]
[ 109853-93-2 ]

Reference： [1]Carbohydrate Research,1986,vol. 158,p. 67 - 80

10
[ 85-29-0 ]
[ 1937-19-5 ]
[ 146470-10-2 ]

Reference： [1]Pharmazie,1992,vol. 47,p. 758 - 764

11
[ 611-98-3 ]
[ 1937-19-5 ]
[ 146470-22-6 ]

Reference： [1]Pharmazie,1992,vol. 47,p. 758 - 764

12
[ 31431-19-3 ]
[ 1937-19-5 ]
[ 146470-26-0 ]

Reference： [1]Pharmazie,1992,vol. 47,p. 758 - 764

13
[ 2011-66-7 ]
[ 1937-19-5 ]
[ 136623-22-8 ]

Reference： [1]Pharmazie,1992,vol. 47,p. 758 - 764

14
[ 1937-19-5 ]
[ 87379-42-8 ]
[ 93583-97-2 ]
[ 113502-38-8 ]

Reference： [1]Bulletin de la Societe Chimique de France,1987,p. 318 - 324
[2]Bulletin de la Societe Chimique de France,1987,p. 318 - 324
[3]Bulletin de la Societe Chimique de France,1987,p. 318 - 324

15
[ 53-03-2 ]
[ 1937-19-5 ]
C₂₃H₃₄N₈O₃ [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1969,vol. 19,p. 69 - 75

16
[ 16214-27-0 ]
[ 1937-19-5 ]
C₁₁H₁₄N₈ [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1979,vol. 14,p. 343 - 346

17
[ 1208-88-4 ]
[ 1937-19-5 ]
[ 6928-03-6 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1961,vol. 4,p. 177 - 182

18
[ 1937-19-5 ]
[ 128072-93-5 ]
5-(5-Chloro-pyridin-2-yl)-1H-[1,2,4]triazol-3-ylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2985 - 2993

19
[ 3722-80-3 ]
[ 1937-19-5 ]
1,2-bis(4-guanylhydrazonophenoxy)propane dihydrochloride [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2004,vol. 39,p. 925 - 929

20
[ 1937-19-5 ]
[ 148063-59-6 ]
2,3-dihydroxyterephthalaldehyde-1,4-bis-guanylhydrazone dihydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1305 - 1308

21
[ 867035-25-4 ]
[ 1937-19-5 ]
[[1-(1H-pyrrolo[2,3-c]pyridin-2-yl)ethylidene]amino]guanidine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride; In ethanol; water; for 1.5h;Heating / reflux;	A mixture of 1-(1H-pyrr ol0[2,3-c]pyridin-2-yl)ethanone (Example 70) (90 mg, 0.56 mmol) and aminoguanidine hydrochloride (65 mg, 0.59 mmol) in ethanol (5.6 mL) and 6 N HCl (0.47 mL) was heated under reflux for 1.5 h. The reaction mixture was cooled to room temperature and the precipitate was filtered, rinsed with ethanol and diethyl ether, and dried under vacuum at 45C to provide [ [ 1- ( 1H-pyrrolo [2, 3-c] pyridin- 2-yl)ethylidene]amino]guanidine dihydrochloride (138 mg, 86%) as a white solid: mp 314-318C dec. ; ¹H NMR (300 MHz, CD30D) No.2.50 (3H, s), 7.40 (1H, s), 8.10-8.27 (2H, m), 9.04 (lH, s) ; ESI MS m/z 217 [C10H12N6 + H] +; HPLC (Method A) >99% (AUC) , tR = 9.01 min.

Reference： [1]Patent: WO2005/97129,2005,A2 .Location in patent: Page/Page column 131-132

22
[ 80-73-9 ]
5-(hexahydro-1H-azepin-1-yl)methyl-2-thiophenecarbonyl chloride [ No CAS ]
[ 1937-19-5 ]
[ 201545-91-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	With hydrogenchloride; sodium hydroxide; In hexane; water; ethyl acetate; acetonitrile;	EXAMPLE 83 1-[5-(5-Amino-1H-1,2,4-triazol-3-yl)-2-thenyl]hexahydro-1H-azepine 500 ml of <strong>[80-73-9]1,3-dimethyl-2-imidazolidinone</strong> and 18.0 g (163.2 mM) of aminoguanidine hydrochloride were added to 24.0 g (81.6 mM) of 5-(hexahydro-1H-azepin-1-yl)methyl-2-thiophenecarbonyl chloride, and the mixture was stirred at room temperature for 1 hour. Then, 16.3 g (60% oil, 408 mM) was added and the mixture was stirred overnight at 130 C. The reaction solution was cooled to room temperature, 50 ml of water and 500 ml of n-hexane were added to effect separation of layers. To the resulting lower layer was added 1,000 ml of saturated brine, and then the mixture was extracted seven times with 500 ml of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, concentrated under a reduced pressure, and 1,000 ml of acetonitrile was added. With ice-cooling, 150 ml of 4 N hydrochloric acid/ethyl acetate was added, and the thus precipitated crystals were collected by filtration. The resulting crystals were added to 200 ml of 1 N sodium hydroxide, extracted three times with 200 ml of ethyl acetate, dried over anhydrous sodium sulfate and then concentrated to 1/10 volume under a reduced pressure. The thus precipitated crystals were collected by filtration to give 10.4 g (51% in yield) of the title compound.

Reference： [1]Patent: US6090804,2000,A

23
[ 1937-19-5 ]
[ 197959-79-8 ]
[ 197958-74-0 ]

Yield	Reaction Conditions	Operation in experiment
93%		A mixture of <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.811 g, 7.33 mmol) and 3-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propionaldehyde (1.28 g, 3.66 mmol, as prepared in the preceding step) in ethanol (30 mL) was stirred overnight at ambient temperature. The mixture was concentrated in vacuo to approximately 15 mL, then dichloromethane (60 mL) was added to precipitate excess <strong>[1937-19-5]aminoguanidine hydrochloride</strong>, The mixture was filtered and the filtrate was concentrated. The residue was dissolved in dichloromethane (30 mL) and extracted with aqueous NaOH (0.04 N, 90 mL). The aqueous layer was extracted with dichloromethane (2 x 30 mL). The combined organic extracts were washed with water (50 mL) and brine (2 x 50 mL), dried over K2CO3, filtered, and evaporated to give the free base of the title compound (1.38 g, 93%) as a gold foam. The acetate salt of the title compound was made by adding glacial acetic acid (0.75 mL, 30 mmol) dropwise to the free base, 2-[2-[3-(2-methoxyphenylsulfonyloxy)-5-methylphenoxy] ethyl-1-methylene]-hydrazinecarboximidamide, (1.03 g, 2.53 mmol, prepared above) in dichloromethane (10 mL). The solvent was removed in vacuo at ambient temperature. The crude acetate salt was purified by flash column chromatography (20% to 100% 1:10:40 acetic acid / methanol dichloromethane in dichloromethane) to give the title compound (0.91 g, 77%) as a white foam. 1H-NMR (300 MHz, CDCl3) delta 7.81 (dd, 1 H, J = 1.7, 7.9 Hz), 7.62 (ddd, 1 H, J = 1.7, 7.5, 8.4 Hz), 7.54 (t, 1 H, J = 5. Hz), 7.09 (d, 1 H, J = 8.4 Hz), 7.02 (td, 1 H, J = 0.9, 7.9 Hz), 6.57 (br s, 1 H), 6.50 (br s, 1 H), 6.46 (br s, 1 H), 4.05 (t, 2 H, J = 6 Hz). 4.01 (s, 3 H), 2.68 (q, 2 H, J = 6 Hz), 2.23 (s, 3 H). Mass spectrum (MALDI-TOF. alpha-cyano-4-hydroxycinnamic acid matrix) calcd. for C18H22N4O5S: 407.1 (M + H). Found: 407.0.

Reference： [1]Patent: EP906091,2006,B1 .Location in patent: Page/Page column 27-28

24
[ 878671-95-5 ]
[ 1937-19-5 ]
[ 878671-96-6 ]

Yield	Reaction Conditions	Operation in experiment
76%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 50℃; for 12h;	The intermediate compound V (13.3mmol, 3.0g), <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (26.6mmol, 2.9g) was added to 50mL of N, N-dimethyl formamide, was added under stirring N, N-diisopropylethylamine amine (39.9mmol, 5.1g), then the reaction 50 12h, the solvent was evaporated to dryness 20mL2M sodium hydroxide was added, and the reaction was continued 50 12h. After stopping the reaction, the reaction mixture was filtered, and the filtrate was washed with dilute hydrochloric acid to pH = 4, shows a large number of white precipitate was filtered, and then at a temperature of 45-50 dried under vacuum to give 2.85g the VI intermediate compound,(76%)
49%		A mixture of <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (3.18 g, 29 mmol), l-cyclopropyl-4- isothiocyanato-naphthalene (3.24 g, 14 mmol) and diisopropylethylamine (3 eq) in DMF (20 mL) was stirred at 50 0C for 15 hours. The solvent was evaporated, toluene was added, and the solvent was evaporated again. A 2.0 M aqueous solution of sodium hydroxide (30 mL) was added and the reaction mixture was heated at 50 0C for 60 hours. The reaction mixture was filtered, and the filtrate was neutralized with a 2.0 M aqueous solution of HCl. New filtration, then evaporation of solvent and purification of the residue by silica gel chromatography to yield 5-amino-4-(4-cyclopropylnaphthalen-l-yl)- 4H-[l,2,4]triazole-3-thiol (2.0 g, 49%).
49%		STEP E: 5-Amino-4-(l-cyclopropylnaphthalen-4-yl)-4H-l,2,4-triazole-3- thiolA mixture of <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (3.18 g, 29 mmol), l-cyclopropyl-4- isothiocyanato naphthalene (3.24 g, 14 mmol) and diisopropylethylamine (3 eq) in DMF (20 mL) was stirred at 50 C for 15 hours. The solvent was removed under reduced pressure, toluene added, and the solvent was evaporated again. Sodium hydroxide solution (2M, 30 mL) was added and the reaction mixture heated at 50 C for 60 hours. The reaction mixture was filtered and the filtrate neutralized with aqueous HCl (2M). The mixture was re-filtered and the solvent removed under reduced pressure. The residue was purified by silica gel chromatography to yield 5-amino-4-(l-cyclopropylnaphthalen-4-yl)-4H-l,2,4-triazole-3- thiol (2.0 g, 49%).

Reference： [1]Patent: CN105566237,2016,A .Location in patent: Paragraph 0066; 0067; 0068
[2]Patent: WO2009/70740,2009,A2 .Location in patent: Page/Page column 89-90
[3]Patent: WO2006/26356,2006,A2 .Location in patent: Page/Page column 21
[4]Patent: WO2011/85009,2011,A2 .Location in patent: Page/Page column 37

25
[ 34328-47-7 ]
[ 1937-19-5 ]
[ 849335-07-5 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6511 - 6514

26
[ 74003-55-7 ]
[ 1937-19-5 ]
[ 849335-02-0 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6511 - 6514

27
[ 89-98-5 ]
[ 1937-19-5 ]
[ 13098-73-2 ]

Yield	Reaction Conditions	Operation in experiment
79.6%	With sodium acetate; In ethanol; at 25 - 80℃; for 6h;	General procedure: General procedure A: To a solution of benzaldehyde (1 eq.) in ethanol (300ml) was sequentially added Aminoguanidine hydrochloride (1 eq.) and sodium acetate (1 eq.) at 25C. The resulting reaction mixture was heated at 80C for next ~6 hours. Reaction completion was monitored on TLC using dichloromethane/methanol (8/2) as mobile phase. After completion of reaction, the reaction mixture was allowed to cool down to 25C and dumped in the saturated solution of NaHC03 (700ml). The resulting precipitate were filtered off under vacuum and washed with water (100ml). The resulting solid material was titurated with diethylether (2 x 25 ml) and dried under vacumm to provide the desired substituted aminoguanidine derivative. The following compounds were prepared according general procedure A: Prepared following general procedure A from 2-chlorobenzaldehyde (10 g) to give 1 1 .1 g of desired compound (yield: 79.6%). 1 H-NMR (DMSO-d6): delta (ppm) 5.66 (s, 2H); 6.05 (s broad, 2H); 7.27 (m, 2H); 7.40 (m, 1 H); 8.14 (dd, 1 H); 8.27 (s, 1 H); MS (ESI+): m/z = 197.2 [M+H]+.
79.6%	With sodium acetate; In ethanol; at 25 - 80℃; for 6h;	General procedure: Prepared following general procedure A from 2-chlorobenzaldehyde (10 g) to givell.lg of desired compound (yield: 79.6%). 1H-NMR (DMSO-d6): (ppm) 5.66 (5, 2H);6.05 (5 broad, 2H); 7.27 (m, 2H); 7.40 (m, 1H); 8.14 (dd, 1H); 8.27 (5, 1H); MS (ESl+):m/z= 197.2 [M+H]. To a solution of benzaldehyde (leq.) in ethanol (300m1) was sequentially added Aminoguanidine hydrochloride (leq.) and sodium acetate (leq.) at 25C. The resulting reaction mixture was heated at 80C for next 6 hours. Reaction completion wasmonitored on TLC using dichloromethane/methanol (8/2) as mobile phase. After completion of reaction, the reaction mixture was allowed to cool down to 25C and dumped in the saturated solution of NaHCO3 (700m1). The resulting precipitate were filtered off under vacuum and washed with water (100m1). The resulting solid material was titurated with diethylether (2 x 25 ml) and dried under vacumm to provide thedesired substituted aminoguanidine derivative.

Reference： [1]Patent: WO2016/1389,2016,A1 .Location in patent: Page/Page column 48
[2]Patent: WO2017/21216,2017,A1 .Location in patent: Page/Page column 20-21; 40
[3]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1623 - 1625

28
[ 50562-79-3 ]
[ 1937-19-5 ]
[ 639855-88-2 ]

Yield	Reaction Conditions	Operation in experiment
69.6%		General procedure: Compound 5 (0.5 mmol) was dissolved in 5mL methanol and 6drops of concentrated hydrochloric acid were added to the solution.The reaction was stirred for 5 min. Then, <strong>[1937-19-5]aminoguanidine hydrochloride</strong>(0.45 mmol) was added to the resulting solution and stirredat 110 C for 2 h. After cooling, the solvent was evaporated invacuo, followed by the purification of the resulting residue by silicagel column chromatography (dichloromethane/methanol 6/1)and acidized with concentrated hydrochloric acid to generate apure solid 6a-6l.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 108 - 118
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277

29
[ 80360-20-9 ]
[ 1937-19-5 ]
[ 1262322-42-8 ]

Yield	Reaction Conditions	Operation in experiment
67.1%		General procedure: Compound 5 (0.5 mmol) was dissolved in 5mL methanol and 6drops of concentrated hydrochloric acid were added to the solution.The reaction was stirred for 5 min. Then, <strong>[1937-19-5]aminoguanidine hydrochloride</strong>(0.45 mmol) was added to the resulting solution and stirredat 110 C for 2 h. After cooling, the solvent was evaporated invacuo, followed by the purification of the resulting residue by silicagel column chromatography (dichloromethane/methanol 6/1)and acidized with concentrated hydrochloric acid to generate apure solid 6a-6l.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 108 - 118
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277

30
[ 1937-19-5 ]
[ 99532-45-3 ]
[ 639855-94-0 ]

Yield	Reaction Conditions	Operation in experiment
30.6%		General procedure: Compound 5 (0.5 mmol) was dissolved in 5mL methanol and 6drops of concentrated hydrochloric acid were added to the solution.The reaction was stirred for 5 min. Then, <strong>[1937-19-5]aminoguanidine hydrochloride</strong>(0.45 mmol) was added to the resulting solution and stirredat 110 C for 2 h. After cooling, the solvent was evaporated invacuo, followed by the purification of the resulting residue by silicagel column chromatography (dichloromethane/methanol 6/1)and acidized with concentrated hydrochloric acid to generate apure solid 6a-6l.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 108 - 118
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277

31
[ 1937-19-5 ]
[ 104142-24-7 ]
[ 1262322-50-8 ]

Yield	Reaction Conditions	Operation in experiment
86.4%		General procedure: Compound 5 (0.5 mmol) was dissolved in 5mL methanol and 6drops of concentrated hydrochloric acid were added to the solution.The reaction was stirred for 5 min. Then, <strong>[1937-19-5]aminoguanidine hydrochloride</strong>(0.45 mmol) was added to the resulting solution and stirredat 110 C for 2 h. After cooling, the solvent was evaporated invacuo, followed by the purification of the resulting residue by silicagel column chromatography (dichloromethane/methanol 6/1)and acidized with concentrated hydrochloric acid to generate apure solid 6a-6l.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 108 - 118
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277

32
[ 1937-19-5 ]
[ 99532-49-7 ]
[ 1262322-51-9 ]

Yield	Reaction Conditions	Operation in experiment
72.3%		General procedure: Compound 5 (0.5 mmol) was dissolved in 5mL methanol and 6drops of concentrated hydrochloric acid were added to the solution.The reaction was stirred for 5 min. Then, <strong>[1937-19-5]aminoguanidine hydrochloride</strong>(0.45 mmol) was added to the resulting solution and stirredat 110 C for 2 h. After cooling, the solvent was evaporated invacuo, followed by the purification of the resulting residue by silicagel column chromatography (dichloromethane/methanol 6/1)and acidized with concentrated hydrochloric acid to generate apure solid 6a-6l.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 166,p. 108 - 118
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7274 - 7277

33
[ 4126-60-7 ]
[ 1937-19-5 ]
[ 1315607-28-3 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5540 - 5561

34
[ 39751-07-0 ]
[ 1937-19-5 ]
2,6-bis(N-guanidino)iminoadamantane dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In ethanol; for 5h;Reflux;	The respective ketone (1.0 mmol) was dissolved in absolute ethanol (10 mL) and then aminoguanidine hydrochloride (1.0 mmol) was added in the solution in one portion. The reaction mixture was refluxed for 5 h and after cooling the solvent was evaporated yielding the crude product quantitatively. The obtained solid was purified by washing with ethyl acetate/methanol solvent mixture and the product was isolated as a white solid. 2,6-Bis(N,N?-guanidino)iminoadamantane dihydrochloride (3)Similar to the synthesis of compound 2, <strong>[39751-07-0]adamantane-2,6-dione</strong> [25] (82 mg, 0.5 mmol) was used in the synthesis of hydrazone 3, yield 171 mg (98%); mp: >300 C; 1H NMR (300 MHz, [D6]DMSO): delta = 1.96-2.07 (m, 8H), 2.70 (s, 2H), 3.46 (s, 2H), 7.47-7.70 (br s, 8H), 11.33 ppm (s, 2H); 13C NMR (75 MHz, [D6]DMSO): delta = 30.9, 36.8, 37.8, 38.1, 39.4, 156.2, 163.1 ppm; IR (KBr): nu = 3316(br), 3165(br), 2939(m), 1661(s), 1635(s), 1598(s), 1449(w), 1107(w) cm-1; HRMS-MALDI m/z [M + H]+ Calcd for C12H20N8: 277.1883. Found: 277.1882.

Reference： [1]Bioorganic Chemistry,2012,vol. 41-42,p. 28 - 34

35
[ 20098-14-0 ]
[ 1937-19-5 ]
[ 1369889-38-2 ]

Yield	Reaction Conditions	Operation in experiment
99%	In ethanol; for 5h;Reflux;	The respective ketone (1.0 mmol) was dissolved in absolute ethanol (10 mL) and then aminoguanidine hydrochloride (1.0 mmol) was added in the solution in one portion. The reaction mixture was refluxed for 5 h and after cooling the solvent was evaporated yielding the crude product quantitatively. The obtained solid was purified by washing with ethyl acetate/methanol solvent mixture and the product was isolated as a white solid. 5-Hidroxy-2-(N-guanidino)iminoadamantane hydrochloride (5)Compound 5 was obtained from 1-hydroxyadamantan-4-one [25] (166 mg, 1.0 mmol) in a 99% yield (256 mg); mp: 269-271 C; 1H NMR (300 MHz, [D6]DMSO): delta = 1.57-1.83 (m, 8H), 2.17 (s, 1H), 2.67 (s, 1H), 3.35 (s, 2H), 3.42 (s, 1H), 4.69 (br s, 1H), 7.54 (br s, 4H), 11.16 (s, 1H) ppm; 13C NMR (75 MHz, [D6]DMSO): delta = 29.5, 32.8, 36.1, 37.5, 39.9, 43.8, 44.0, 45.3, 65.6, 156.2, 164.8 ppm; IR (KBr): (br), 3165(br), 2929(m), 2911(m), 2858(m), 1670(s), 1647(s), 1602(s), 1455(w), 1353(w), 1112(m), 1093(m), 926(w) cm-1; HRMS-MALDI m/z [M + H]+ Calcd for C11H18N4O: 223.1553. Found: 223.1553.

Reference： [1]Bioorganic Chemistry,2012,vol. 41-42,p. 28 - 34

36
[ 10181-17-6 ]
[ 1937-19-5 ]
C₂₁H₃₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		EXAMPLE 9; (E)- 15-Guanidinoimino- 13-isopropylpodocarpa-8, 11, 13-triene; A solution of 80 mg of <strong>[1937-19-5]aminoguanidine hydrochloride</strong> in 0.8 ml of IN HC1 was added to a solution 200 mg of 13-isopropylpodocarpa-8, 11, 13-triene- 15-aldehyde in 1 ml of dioxane. The mixture was heated to 80 C for 5 hours. After coohng, the solvent was removed under reduced pressure and the crude reaction mixture was purified by flash chromatography using DCM/MeOH/NH4OH 90/10/1 as eluent. The pure fractions were evaporated to dryness. The title compound was obtained as a white solid.Yield: 92% (221 mg).-NMR (300 MHz, DMSO-de) delta: 7.15 (d, 1H), 7.09 (s, 1H), 6.95 (dd, 1H), 6.83 (d, 1H), 5.50 (bb, 2H), 5.16 (bb, 2H), 2.76 (m, 3H), 2.28 (m, 1H), 1.80-1.20 (m, 8H), 1.15 (s, 3H), 1.14 (d, 6H), 1.11 (s, 3H).MS: 340 (M+).

Reference： [1]Patent: WO2012/55894,2012,A1 .Location in patent: Page/Page column 15-16

37
[ 131394-26-8 ]
[ 1937-19-5 ]
di(aminoguanidium) 4,4',5,5'-tetranitro-2,2'-biimidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium hydroxide; In methanol; water; at 60℃;	Example 2Synthesis of di(aminoguanidium) 4,4',5,5'-tetranitro-2,2'-biimidazole4,4',5,5'-tetranitro-2,2'-biimidazole (10 g, 0.032 mol) and MeOH (200 mL) were placed into a 500 mL reactor and stirred until TNBI was all dissolved while maintaining the temperature of a reaction solution at 60 C. KOH (2 equivalents, 7 g) was dissolved in 100 mL of water and added to a reaction solution. At this time, the solution became a dark yellowish dispersion solution state. When aminoguanidium hydrochloride (2.2 equivalents, 8 g) was added to the mixed solution and then stirred, the solution became darker and darker while occurring ion exchange reaction until it was eventually a dark orange color. Though the ion exchange reaction occurred within several minutes, the solution was sufficiently stirred for 3 to 4 hours to completely accomplish ion exchange. After stirring, the solution was cooled down to normal temperature and filtered out, and then the obtained solid matter was cleaned with ice water. The obtained solid matter was dried to obtain 13.1 g of di(aminoguanidium) 4,4',5,5'-tetranitro-2,2'-biimidazole (Yield: 73%).IR (neat): v 3423, 3395, 3289, 3096, 1666, 1592, 1520, 1466, 1373, 1303, 1191, 1110, 911, 856, 810, 7511H NMR (300 MHz, DMSO) delta (ppm) 8.9 (bs, 1H), 7.16 (bs, 4H), 4.72 (bs, 2H); 13C NMR (75 MHz, DMSO) delta (ppm) 158.91, 143.84, 140.41

Reference： [1]Patent: US2012/203008,2012,A1 .Location in patent: Page/Page column 2

38
[ 542-85-8 ]
[ 1937-19-5 ]
[ 17697-93-7 ]

Yield	Reaction Conditions	Operation in experiment
77%		REPRESENTATIVE PROCEDURE 32) NaHC03 H20, RefluxStep 1 16h,Step 2 a. PREPARATION OF 5-AMINO-4-ETHYL-4H-1,2,4-TRIAZOLE-3-THIOL[00542] To a solution of <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (3.0 g, 27.3 mmol) in 20.0 mL of ethanol was added ethyl isothiocyanate (2.9 mL, 32.7mmol). This solution was heated in a microwave reactor for 20 min at 150C, cooled to room temperature and concentrated. The crude reaction mixture was re-dissolved 30 ml of water and K2CO3 (4.5 g, 32.7 mmol) was added. The reaction was allowed to reflux for 16 h. The reaction was allowed tocool to room temperature, diluted with methanol and concentrated. The residue was purified by column chromatography with methanol/CELC . (1 :6) to afford 3.03 g (77%) of the desired product
77%		[00446] To a solution of isonicotinohydrazide (84 mg, 0.61 mmol) in 1.0 mL of ethanol was added ethyl isothiocyanate (64 mu, 0.74 mmol). This reaction mixture was heated in a microwave reactor for 15 min at 150C, cooled to room temperature and concentrated. The residue was then re-dissolved 10 ml of H2Oand K2CO3 (101.5 mg, 0.74 mmol) was added, then the solution was brought to reflux. After 16 h,the reaction was allowed to cool to room temperature, diluted with methanol and concentrated. The residue was purified by column chromatography with methanol/CH2Cl2 (1 :6) to afford 67 mg (53%) of the title compound. lH NMR (MeOD) 58.78 (d, J = 5.5 Hz, 2H), 7.78 (d, J = 6.2 Hz, 2H), 4.26 (q, J = 7.2, 2H), 1.33 (t, J = 7.3 Hz, 3H)LRMS calculated for C9Hi0N4S (M+H)Vz: 207.06. Measured 207.1 m/z.

Reference： [1]Patent: WO2012/154403,2012,A2 .Location in patent: Page/Page column 255-256
[2]Patent: WO2016/154471,2016,A1 .Location in patent: Paragraph 00447

39
[ 131394-26-8 ]
[ 1937-19-5 ]
bis(aminoguanidinium) 4,4',5,5'-tetranitro-2,2'-biimidazolate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		Add 10.0 g(0.032 mol) of 4,4'-5,5'-tetranitro-2,2'-biimidazole and 200 mL of methanol to a 500 mL round flask and set the solution temperature to 60 oC. Wait until all of the 4,4'-5,5'-tetranitro-2,2'-biimidazole dissolves. Next, dissolve 7.7 g of KOH (0.070 mol, 2.2 eq.) in 100mL of water and add this to the 4,4'-5,5'-tetranitro-2,2'-biimidazole solution. After mixing this solution, it will turn into a dark yellowish suspension. Next, add 8.0 g (0.070 mol, 2.2 eq.) of aminoguanidium hydrochloride to this mixture. This produces anion exchange reaction that causes the solution to gradually turn dark orange. Allow the reaction to 3-4 h until completion. Next,cool the solution to 25 oC, filter it, and then wash the filtrate with ice water. After drying, 13.1 g of di(aminoguanidium)-4,4'-5,5'-tetranitro-2,2'-biimidazole (5) was obtained (yield: 73%).

Reference： [1]Bulletin of the Korean Chemical Society,2013,vol. 34,p. 2503 - 2506

40
[ 1937-19-5 ]
[ 31795-44-5 ]
C₆H₈N₄O₄S [ No CAS ]

Reference： [1]Australian Journal of Chemistry,2014,vol. 67,p. 1005 - 1010

41
[ 1937-19-5 ]
[ 1544-68-9 ]
5-amino-4-(4-fluorophenyl)-4H-[1,2,4]triazole-3-thiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		5-Amino-4-(4-fluoro-phenyl)-4H-[l,2,4]triazole-3-thiol4- fluorophenylisothiocyanate (1.04 g, 6.54 mmol), aminoguanidinium chloride (1.45 g, 13.1 mmol), diisopropylethylamine (3.12 mL, 19.6 mmol) are dissolved in DMF (9.40 mL). Reaction mixture is stirred at 50C for 15 h, then evaporated to dryness. 13 mL of NaOH aq 2M are then added, and reaction mixture is stirred at 50 C for 18 hours. Suspension is then filtered, and filtrate is neutralized by addition of HC1 aq 2M and filtrated. Both precipitates are pulled together, to give 1.2 g of an orange powder (87%). MS [M+H]+ m/z = 210.91H-RMN (DMSO- 6) : delta (ppm) 5.96 (s, 2H) ; 7.38 (m, 4H) ; 12.80 (s)

Reference： [1]Patent: WO2015/189330,2015,A1 .Location in patent: Page/Page column 49; 50

42
[ 3163-76-6 ]
[ 1937-19-5 ]
((2E,2'E,2''E)-2,2',2''-(benzene-1,3,5-triyltris(methanylylidene))tris(hydrazin-1-yl-2-ylidene))tris(aminomethaniminium) chloride [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 52,p. 386 - 389

43
C₂N₅O₅^(1-)*Ag⁽¹⁺⁾ [ No CAS ]
[ 1937-19-5 ]
C₂HN₅O₅*CH₆N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	In water; at 20℃; for 12h;	General procedure: A solution of guanidinium chloride (1 mmol), aminoguanidinium chloride (1 mmol), or triaminoguanidinium chloride (1 mmol) in water (2 mL) was added dropwise to the suspension of precursor salt 1-b (0.5 mmol) in water (10 mL). The mixture was stirred at room temperature for 12 h. The precipitate was filtered off, and the filtrate was dried under vacuum yielding crude product. Pure samples suitable for elemental analysis were prepared by recrystallization from water.

Reference： [1]Chinese Chemical Letters,2016,vol. 27,p. 433 - 436

44
[ 1937-19-5 ]
[ 18458-71-4 ]
2-((cis-2,6-diphenyldihydro-2H-pyran-4(3H)-ylidene)hydrazinecarboximidamide) hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In ethanol; at 100℃; for 0.0833333h;Microwave irradiation;	General procedure: The hydrazones were prepared by reaction of ketones with <strong>[1937-19-5]aminoguanidine hydrochloride</strong> withthe aid of a microwave device. A mixture of 2,6-di-substituted-tetrahydropyran-4-one (0.5 mmol)and <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.5 mmol) in 1 mL of ethanol were placed in a glass tube forspecific microwave reactor along with a magnetic. A shaker reaction was performed under microwaveirradiation to 100 C (read monitored by infrared sensor) for 5 min (?Hold Time?) under conditions ofa closed vessel. After completion of the reaction, the solvent was evaporated under reduced pressure.This crude product was then subjected to flash column chromatography to yield a solid. 2-(2,6-Diphenyl-2H-pyran-4(3H)-ylidene)hydrazinecarboximidamide (2). This product was obtainedusing 0.5 mmol of 2,6-diphenyl-tetrahydropyran-4-one (8a). The product was purified by columnchromatography on silica gel using methanol/EtOAc (1:9) as eluent, resulting in quantitative yield(100%). IR (KBr) gamma/cm1 3348, 3309, 3155, 3062, 3035, 2862, 1674, 1597, 1627, 1492, 1091, 1064, 756,698; 1H-NMR (200 MHz, CD3OD) delta 7.36 (m, 10H), 4.68 (m, 2H), 3.17 (dt, 1H, J = 16.0, 2.0 Hz), 2.76(dt, 1H, J = 14.0, 2.0 Hz), 2.51 (dd, 1H, J = 14.0, 12.0 Hz), 2.27 (dd, J = 14.0, 12.0 Hz, 1H); 13C-NMR(50 MHz, CD3OD) delta 159.01, 158.57, 144.10, 130.80, 130.24, 128.20, 82.20, 44.71, 38.37; Anal. Calcd forC18H21ClN4O C, 62.69; H, 6.14; N, 16.25; Found C, 62.27, H, 6.24, N, 16.15.

Reference： [1]Molecules,2016,vol. 21

45
2,6-bis(4-fluorophenyl)tetrahydropyran-4-one [ No CAS ]
[ 1937-19-5 ]
2-((cis-2,6-bis(4-fluorophenyl)dihydro-2H-pyran-4(3H)-ylidene)hydrazinecarboximidamide) hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In ethanol; at 100℃; for 0.0833333h;Microwave irradiation;	General procedure: The hydrazones were prepared by reaction of ketones with <strong>[1937-19-5]aminoguanidine hydrochloride</strong> withthe aid of a microwave device. A mixture of 2,6-di-substituted-tetrahydropyran-4-one (0.5 mmol)and <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.5 mmol) in 1 mL of ethanol were placed in a glass tube forspecific microwave reactor along with a magnetic. A shaker reaction was performed under microwaveirradiation to 100 C (read monitored by infrared sensor) for 5 min (?Hold Time?) under conditions ofa closed vessel. After completion of the reaction, the solvent was evaporated under reduced pressure.This crude product was then subjected to flash column chromatography to yield a solid.

Reference： [1]Molecules,2016,vol. 21

46
2,6-di(naphthalen-2-yl)tetrahydropyran-4-one [ No CAS ]
[ 1937-19-5 ]
C₂₆H₂₄N₄O*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	In ethanol; at 100℃; for 0.0833333h;Microwave irradiation;	General procedure: The hydrazones were prepared by reaction of ketones with <strong>[1937-19-5]aminoguanidine hydrochloride</strong> withthe aid of a microwave device. A mixture of 2,6-di-substituted-tetrahydropyran-4-one (0.5 mmol)and <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.5 mmol) in 1 mL of ethanol were placed in a glass tube forspecific microwave reactor along with a magnetic. A shaker reaction was performed under microwaveirradiation to 100 C (read monitored by infrared sensor) for 5 min (?Hold Time?) under conditions ofa closed vessel. After completion of the reaction, the solvent was evaporated under reduced pressure.This crude product was then subjected to flash column chromatography to yield a solid.

Reference： [1]Molecules,2016,vol. 21

47
[ 1937-19-5 ]
bis(aminoguanidinium)dodecahydroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71.3%	With silver(I) dodecahydro-closo-dodecaborane; In water; at 20℃; for 4h;	General procedure: The silver salt of closo-dodecaborate [Ag2(B12H12)] (1.07 g, 3.0 mmol) was dispersed in 15 ml of deionized water in a 100 ml round-bottom flask. In another flask, hydrazinium bromide (0.68 g, 6.0 mmol) was dissolved in 10 ml of deionized water. The second solution was added slowly to the dispersion of Ag2(B12H12), and stirring was continued for a further 2 h at room temperature. The reaction mixture was then filtered and the residue was washed with 5 ml of deionized water twice. All portions of the filtrate were collected and evaporation of the solvent under reduced pressure yielded a colorless solid compound, which was further dried by applying a high vacuum for 2 h.

Reference： [1]Polyhedron,2016,vol. 115,p. 105 - 110

48
[ 131543-46-9 ]
[ 1937-19-5 ]
[ 1120-99-6 ]
C₃H₆N₄O [ No CAS ]

Reference： [1]ChemMedChem,2016,p. 1778 - 1789

49
[ 1937-19-5 ]
[ 10111-08-7 ]
(E)-4-(1H-imidazol-2-yl)-1,1-diamino-2,3-diazabuta-1,3-diene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 7574 - 7583

50
[ 910222-77-4 ]
[ 1937-19-5 ]
(E)-2-((E)-1-(4-chlorophenyl)-3-(2,4,6-trimethoxyphenyl)allylidene)hydrazinecarboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With hydrogenchloride; In ethanol; for 0.5h;Reflux;	General procedure: The mixture of the chalcones37 1e4 (1 mmol) and aminoguanidineHCl (1 mmol) in 2mL EtOH (99.9%) and conc. HCl (0.2 mL) was heated under reflux for 0.5-1 h (TLC). The cooled reactionmixturewas concentrated under vacuum rotary evaporation.The crude reaction mixture was dissolved in water and extracted with n-butanol (3 25 mL). The organic layers were combined and dried under vacuum. Conjugated guanylhydrazones 1a-4a were recrystallized using EtOAc/hexane (50:50) to obtain 1a-4a in 66-75 yields %.

Reference： [1]Tetrahedron,2018,vol. 74,p. 2857 - 2864
[2]Journal of Organic Chemistry,2016,vol. 81,p. 7574 - 7583

51
[ 3988-77-0 ]
[ 1937-19-5 ]
5-phenyl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator. 5-Phenyl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride (2a) Yellowish solid; mp266-268 C; IR (KBr)nu / cm-1 3337, 3115, 1609,1430; 1H NMR (400 MHz,DMSO-d6) delta 7.97 (bs, 4H,C(NH2)2), 7.86 (d, 1H,J 5.0 Hz, T-H), 7.57 (d,1H, J 3.6 Hz, T-H), 7.39 (d, 2H, J 7.6 Hz, Ph-H), 7.35-7.32(m, 1H, Ph-H), 7.25 (d, 2H, J 7.4 Hz, Ph-H), 7.20-7.17 (m,1H, T-H), 6.02 (dd, 1H, J 2.4, 11.0 Hz, Hx?), 4.11 (dd, 1H,J 11.2, 17.8 Hz, Hm?), 3.36 (dd, 1H, J 2.7, 17.8 Hz, Ha?);13C NMR (101 MHz, DMSO-d6) delta 153.2, 153.0, 139.6,132.7, 132.0, 131.3, 129.0, 128.2, 125.3, 60.4, 44.4; HRMSm/z, [M + H]+ calcd. for C14H15N4S: 271.1017; found:271.1015. T-H: thiophene hydrogens; ?Ha, Hm and Hx:pyrazolyl ring hydrogens.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

52
3-(2-methoxyphenyl)-1-(thiophen-2-yl)prop-2-en-1-one [ No CAS ]
[ 1937-19-5 ]
5-(2-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

53
[ 41066-95-9 ]
[ 1937-19-5 ]
5-(2-bromophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

54
[ 13982-55-3 ]
[ 1937-19-5 ]
5-(3-nitrophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

55
[ 79442-34-5 ]
[ 1937-19-5 ]
5-(4-methylphenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

56
(2E)-1-(thiophen-2-yl)-3-[4-(trifluoromethyl) phenyl] prop-2-en-1-one [ No CAS ]
[ 1937-19-5 ]
5-(4-trifluoromethylphenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

57
[ 1937-19-5 ]
[ 6028-93-9 ]
5-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

58
[ 1937-19-5 ]
[ 367-00-0 ]
5-(4-fluorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

59
[ 79442-37-8 ]
[ 1937-19-5 ]
5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

60
[ 42292-00-2 ]
[ 1937-19-5 ]
5-(4-bromophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

61
[ 7402-71-3 ]
[ 1937-19-5 ]
5-(2,4-dichlorophenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

62
[ 74441-58-0 ]
[ 1937-19-5 ]
5-(3,4-dimethoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium hydroxide; In ethanol; at 55 - 60℃;Sonication; Green chemistry;	General procedure: To a 50 mL vial containing a solution of 3-aryl-1-(thiophen-2-yl)prop-2-en-1-ones 1a-l (1 mmol) in ethanol(15 mL), the <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (0.22 g,2 mmol) and KOH (0.11 g, 2 mmol) were added. Thereaction mixture was sonicated for the time indicated inTable 1 and the reaction temperature reached 55-60 Cafter 10 minutes. The resulting solution was cooled to roomtemperature and acidified using 10% HCl (10-15 mL).The salts were extracted with chloroform (3 × 20 mL)and the combined organic layer was dried over anhydrousmagnesium sulfate. Removal of solvent under vacuumafforded a crude material. The pure products 2a-l wereobtained as amorphous solids with yields of 62-95%after recrystallization from ethyl acetate and drying in adesiccator.

Reference： [1]Journal of the Brazilian Chemical Society,2017,vol. 28,p. 217 - 224

63
2-methyl-1-(quinolin-4-yl)prop-2-en-1-one [ No CAS ]
[ 1937-19-5 ]
4-methyl-3-(quinolin-4-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium hydroxide; In ethanol; water; at 80 - 90℃; for 1h;	General procedure: Example 23 5-methyl-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide exemplified by its hydrochloride salt (0119) NaOH (0.2 mL, 1 eq) was added to a solution of 1-(naphthalen-1-yl)but-2-en-1-one (196 mg, 1.0 mmol) and <strong>[1937-19-5]aminoguanidine hydrochloride</strong> 111 mg, 1.0 mmol) in 96% EtOH (2 mL). The reaction mixture was stirred at 80-90C for 1 h and was then cooled to room temperature, acidified with 1.5 eq HCl/EtOH (1 M, 1.5 mL), and then heated again at boiling point to reduce the volume to approx. 2 mL. The product was purified by column chromatography (SiO2 EtOAc-AcOH, 99:1, then EtOAc-MeOH-AcOH, 99:99:2) and crystallized from MeOH-EtOAc to give the title compound (175 mg, 61%)

Reference： [1]Patent: EP3109237,2016,A1 .Location in patent: Paragraph 0119; 0120; 0236; 0237

64
[ 128113-46-2 ]
[ 1937-19-5 ]
5-methyl-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium hydroxide; In ethanol; water; at 80 - 90℃; for 1h;	Example 23 5-methyl-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazole-1-carboximidamide exemplified by its hydrochloride salt (0119) NaOH (0.2 mL, 1 eq) was added to a solution of 1-(naphthalen-1-yl)but-2-en-1-one (196 mg, 1.0 mmol) and <strong>[1937-19-5]aminoguanidine hydrochloride</strong> 111 mg, 1.0 mmol) in 96% EtOH (2 mL). The reaction mixture was stirred at 80-90C for 1 h and was then cooled to room temperature, acidified with 1.5 eq HCl/EtOH (1 M, 1.5 mL), and then heated again at boiling point to reduce the volume to approx. 2 mL. The product was purified by column chromatography (SiO2 EtOAc-AcOH, 99:1, then EtOAc-MeOH-AcOH, 99:99:2) and crystallized from MeOH-EtOAc to give the title compound (175 mg, 61%) . 1H NMR (CD3OD, 400 MHz) delta: 1.43 (d, 3H), 3.37 (dd, 1H), 4.00 (dd, 2H), 4.76 (m, 1H), 7.55-7.62 (m, 2H), 7.67 (t, 1H), 7.83 (d, 1H), 7.96 (d, 1H), 8.03 (d, 1H), 9.02 (d, 1H).

Reference： [1]Patent: EP3109237,2016,A1 .Location in patent: Paragraph 0119; 0120

65
[ 6552-63-2 ]
[ 1937-19-5 ]
7-(4-chlorophenyl)-5-(4-methoxyphenyl)-5,6-dihydro-4H-1,2,4-triazepin-3-ylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With iodine; In ethanol; water; for 1.5h;Reflux;	General procedure: A mixture of 1,3-diarylpropenone 1a-h (1 mmol), aminoguanidine hydrochloride 2 (2 mmol) and molecular iodine (20 molpercent) in 10 mL of aqueous ethanol (4:1) was refluxed for the appropriate time, mentioned in Table IV. Progress of the reaction was monitored by TLC plate (using iodine for the revelation of spots). After completion, the reaction mixture was treated with a dilute aqueous solution of Na2S2O3. A pale white crude solid separated out which was filtered, washed and dried. The products were found to be single spots on TLC plate examination and were subjected to further purification by column chromatography using silica gel with petroleum ether:ethyl acetate (9:1, v/v) as eluent to afford 5,7-diaryl-1,2,4-triazepine-3-ylamines in good yields.

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 585 - 589

66
1-(4-acetylphenyl)-3-(4-tert-butylphenyl)urea [ No CAS ]
[ 1937-19-5 ]
2-{1-[4-(3-(4-(tert-butyl)phenyl)ureido)phenyl]ethylidene}hydrazine-1-carboximidamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With lithium chloride; In ethanol; at 78℃;	General procedure: The methyl ketones (17 and 19, 0.5 mmol) were dissolved in absolute ethanol (10 mL), and <strong>[1937-19-5]aminoguanidine hydrochloride</strong> (111 mg, 1 mmol) and a catalytic amount of LiCl(10 mg) were added. The reaction mixture was heated under reflux for 12-24 h. The solvent was evaporated under reduced pressure.The crude product was purified by crystallization from 70% methanol, then recystalization again from ethyl acetate to afford the final products as listed below: 4.1.4.1. 2-{1-[4-(3-(4-(tert-Butyl)phenyl)ureido)phenyl]ethylidene}hydrazine-1-carboximidamide (17). Buff solid (76%): mp > 300 C.1H NMR (DMSO-d6) delta 9.70 (brs, 1 H), 8.60 (brs, 1 H), 7.72 (d,J 8.7 Hz, 2 H), 7.41 (d, J 8.7 Hz, 2 H), 7.37 (d, J 8.7 Hz, 2 H), 7.27(d, J 8.7 Hz, 2 H), 5.83 (brs, 2 H), 5.43 (brs, 2 H), 2.19 (s, 3 H),1.24 (s,9 H); 13C NMR (DMSO-d6, 100 MHz) delta 160.20, 153.41, 148.19, 145.02,140.08, 137.97, 134.64, 126.82, 126.28, 119.00, 118.39, 34.78, 32.17,14.20; ESIMS m/z (rel intensity) 367 ([M+H]+,100); HRMS (ESI), m/z 367.2252 M+, calcd for C20H27N6O 367.2241.