[ CAS No. 6629-04-5 ] {[proInfo.proName]}

Name: 6629-04-5|N-Cyanoacetylurethane|95%
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SKU: A252429
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Quality Control of [ 6629-04-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 6629-04-5 ]

SDS Specification

Alternatived Products of [ 6629-04-5 ]

Product Details of [ 6629-04-5 ]

CAS No. :	6629-04-5	MDL No. :	MFCD00001937
Formula :	C₆H₈N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HSOGVWWWGVFXGF-UHFFFAOYSA-N
M.W :	156.14	Pubchem ID :	23112
Synonyms :

Calculated chemistry of [ 6629-04-5 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.38
TPSA :	79.19 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) :	-7.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.36
Log Po/w (XLOGP3) :	-0.02
Log Po/w (WLOGP) :	0.17
Log Po/w (MLOGP) :	-0.68
Log Po/w (SILICOS-IT) :	-0.32
Consensus Log Po/w :	-0.1

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.47
Solubility :	53.5 mg/ml ; 0.342 mol/l
Class :	Very soluble
Log S (Ali) :	-1.19
Solubility :	10.0 mg/ml ; 0.0641 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.84
Solubility :	22.6 mg/ml ; 0.145 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 6629-04-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 6629-04-5 ]

* 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 [ 6629-04-5 ]
Downstream synthetic route of [ 6629-04-5 ]

[ 6629-04-5 ] Synthesis Path-Upstream 1~1

1
[ 372-09-8 ]
[ 51-79-6 ]
[ 6629-04-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With trichlorophosphate In N,N-dimethyl-formamide; toluene at 0 - 70℃; for 1.5 h; Inert atmosphere	To a solution of A (120 g, 1410 mmol), ethyl carbamate (108 g, 706 mmol) in dry toluene (500 mL) at 0°C under nitrogen was slowly added DMF (29 ml), then POCl₃ (66 ml, 730 mmol). Reaction mixture was heated at 70°C for 1.5 h, monitored by TLC. After cooling to room temperature, solvent and POCl₃ were removed, and reaction quenched with ice water (100 mL). Precipitate was filtered to give B (210 g, 95percent) as white solid.
89.2%	With trichlorophosphate In N,N-dimethyl-formamide; toluene at 70℃; for 1.5 h;	Commercially available 2-cyanoacetic acid (8.50g) and ethylcarbamate (9.80g) are dissolved in 25mL toluene and 2. 5mL N’ ,N’ -dimethylformamide (DMF). After phosphoryl chloride (4.9OmL) is added drop wise, the solution is showing yellow color. Reaction mixture is then heated to 70°C, and kept for 1.5 hours. After reaction finished, the reaction mixture is cooled to room temperature and poured into 1 OOg ice water. Aqueous layer is then extracted with ethyl acetate (3 x25OmL), and washed with brine (lOOmL). After drying over anhydrous Na2SO4, filtration, pale yellow solid is generated after evaporating all volatiles. This yellow solid is then subjected to a silica gel flash column chromatography (3percent MeOHJDCM) to result a white powder compound Al (15.61g, 89.2percent). Rf = 0.35 (5percent CH3OH/DCM). 1H-NMR (400MHz, DMSO-d6) 3 (ppm): 10.99 (C3NHC4, s, 1H), 4.12 (C2H, q, J = 4.72Hz, 2H), 4.09 (C5H, s, 2H), 1.21 (C1H, t, J =4.72Hz, 3H). 13C-NMR (600MHz, DMSO-d6) (ppm): 164.18 (C4), 151.61 (C3), 115.25 (C6), 61.49 (C2), 27.74(C5), 14.08 (C1). HRMS (ESI) m/z calculated for C6H8N2O3+H 157.0613, found 157.0627. Formula is confimed as C6H8N203.
67%	With trichlorophosphate In N,N-dimethyl-formamide; toluene at 70℃; for 2 h;	2-cyanoacetic acid (85 g, 1 mol) and ethyl aminoformate (89 g, 1 mol) were added to toluene (500 mL). To the mixture was slowly added phosphorus oxychloride (45 mL, 0.5 mol), and then added DMF (5 mL). The reaction was conducted at 70° C. for 2 h. After cooling, water (500 mL) was added to the reaction solution to quench phosphorus oxychloride. The reaction is filtered by suction. The filtered cake was washed with ethyl ether and dried to produce a white solid (104 g) in a yield of 67percent.

Reference： [1] Patent: WO2014/190199, 2014, A1, . Location in patent: Paragraph 00250
[2] Patent: WO2016/81522, 2016, A1, . Location in patent: Paragraph 00284; 00285; 00290
[3] Organic and Biomolecular Chemistry, 2010, vol. 8, # 19, p. 4281 - 4288
[4] Patent: US2013/252958, 2013, A1, . Location in patent: Paragraph 0094
[5] Angewandte Chemie - International Edition, 2017, vol. 56, # 42, p. 13011 - 13015[6] Angew. Chem., 2017, # 129, p. 13191 - 13195,5
[7] Chemische Berichte, 1909, vol. 42, p. 742
[8] Journal of the Chemical Society, 1956, p. 4118,4120

[ 6629-04-5 ] Synthesis Path-Downstream 1~88

1
[ 6629-04-5 ]
[ 123-30-8 ]
[ 30487-56-0 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1970,vol. 6,p. 1016 - 1018
Khimiya Geterotsiklicheskikh Soedinenii,1970,vol. 6,p. 1088 - 1091

3
[ 6629-04-5 ]
[ 104-94-9 ]
[ 30487-54-8 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1970,vol. 6,p. 1016 - 1018
Khimiya Geterotsiklicheskikh Soedinenii,1970,vol. 6,p. 1088 - 1091

4
[ 6629-04-5 ]
[ 78-39-7 ]
[ 36980-62-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 1380 - 1388

5
[ 6629-04-5 ]
[ 122-51-0 ]
[ 1187-34-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 1380 - 1388

6
[ 6629-04-5 ]
[ 62-53-3 ]
[ 4260-38-2 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1970,vol. 6,p. 1016 - 1018
Khimiya Geterotsiklicheskikh Soedinenii,1970,vol. 6,p. 1088 - 1091

7
[ 6629-04-5 ]
[ 156-43-4 ]
[ 4260-39-3 ]

Reference： [1]Chemistry of Heterocyclic Compounds,1970,vol. 6,p. 1016 - 1018
Khimiya Geterotsiklicheskikh Soedinenii,1970,vol. 6,p. 1088 - 1091

8
[ 6629-04-5 ]
[ 78-93-3 ]
[ 76872-71-4 ]

Reference： [1]Indian Journal of Chemistry,1971,vol. 9,p. 1209 - 1212

9
[ 673-22-3 ]
[ 6629-04-5 ]
[ 77362-42-6 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 203 - 207

10
[ 14150-95-9 ]
[ 6629-04-5 ]
[ 118813-38-0 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 626 - 632

11
[ 14150-95-9 ]
[ 6629-04-5 ]
[ 118813-45-9 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 626 - 632

12
[ 672-13-9 ]
[ 6629-04-5 ]
[ 77362-41-5 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 203 - 207

14
[ 6629-04-5 ]
[ 353-85-5 ]
[ 98577-47-0 ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 4642

15
[ 6629-04-5 ]
[ 1666-03-1 ]
[ 74901-21-6 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 203 - 207

16
[ 6629-04-5 ]
[ 1147-43-9 ]
[ 83132-66-5 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1982,vol. 47,p. 1746 - 1756

17
[ 6629-04-5 ]
[ 74901-08-9 ]
[ 74901-09-0 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 203 - 207

18
[ 6629-04-5 ]
[ 133568-67-9 ]
[ 133568-70-4 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2967 - 2976

19
[ 6629-04-5 ]
[ 133568-66-8 ]
[ 133568-69-1 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1990,vol. 55,p. 2967 - 2976

20
[ 6629-04-5 ]
[ 77441-94-2 ]
[ 77442-00-3 ]

Reference： [1]Pharmazie,1980,vol. 35,p. 744 - 745

21
[ 6629-04-5 ]
[ 57716-09-3 ]
[ 74875-28-8 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1083 - 1087

22
[ 6629-04-5 ]
[ 77441-98-6 ]
[ 77441-99-7 ]

Reference： [1]Pharmazie,1980,vol. 35,p. 744 - 745

23
[ 6629-04-5 ]
[ 74875-19-7 ]
[ 74875-23-3 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1083 - 1087

24
[ 6629-04-5 ]
3,5-Dibromo-4-(morpholine-4-sulfonyl)-phenylamine [ No CAS ]
[ 343802-47-1 ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1083 - 1087

25
[ 6629-04-5 ]
[ 83437-14-3 ]
[ 83437-15-4 ]

Reference： [1]Journal of Medicinal Chemistry,1983,vol. 26,p. 96 - 100

26
[ 6629-04-5 ]
[ 83-07-8 ]
[ 135656-54-1 ]

Reference： [1]Archiv der Pharmazie,1991,vol. 324,p. 467 - 468

27
[ 6629-04-5 ]
[ 551-93-9 ]
[ 83132-63-2 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1982,vol. 47,p. 1746 - 1756

28
[ 6629-04-5 ]
[ 82-45-1 ]
[ 83132-67-6 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1982,vol. 47,p. 1746 - 1756

29
[ 6629-04-5 ]
[ 100-52-7 ]
2-cyano-N-(ethoxycarbonyl)-3-phenyl-2-propenamide [ No CAS ]

Reference： [1]Liebigs Annalen der Chemie,1993,p. 625 - 628

30
[ 6629-04-5 ]
[ 90-02-8 ]
[ 74901-20-5 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 203 - 207

31
[ 6629-04-5 ]
[ 148-53-8 ]
[ 74901-31-8 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 203 - 207

32
[ 6629-04-5 ]
[ 635-93-8 ]
[ 77362-40-4 ]

Reference： [1]Heterocycles,1981,vol. 16,p. 203 - 207

33
[ 6629-04-5 ]
[ 122-51-0 ]
[ 1187-34-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404
[2]Journal of Physical Organic Chemistry,2005,vol. 18,p. 1183 - 1189

34
[ 6629-04-5 ]
[ 75-64-9 ]
[ 122-51-0 ]
1-t-butyl-5-cyanouracil [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404

35
[ 6629-04-5 ]
[ 109-73-9 ]
[ 122-51-0 ]
[ 7153-60-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404

36
[ 6629-04-5 ]
[ 122-51-0 ]
[ 62-53-3 ]
[ 6275-84-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404

37
[ 75-15-0 ]
[ 6629-04-5 ]
potassium 2-cyano-3-(ethoxycarbonylamino)-3-oxoprop-1-ene-1,1-bis-thiolate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.3%		A solution of compound Al (3. 12g) and potassium carbonate (2.75g) in DMF (5OmL) is stirred at room temperature for 2 hours. 2.6mL carbon disulfide is added to the reaction suspension, and then kept stirring for 4 hours. After completion of the reaction, 100% ethanol is added to reaction mixture at 0C. Yellow precipitate is generated and filtered out. After washing with diethyl ether and drying under reduced pressure overnight, pale yellow solid, compound A2 is obtained in a yield of 92.3%. 1H-NMR (400MHz, DMSO-d6) 5 (ppm):14.92 (C3NHC4, s, 1H), 3.99 (C2H, q, J = 4.72Hz, 2H), 1.16 (C1H, t, J =4.72Hz, 3H). 13C- NMR (600MHz, DMSO-d6) 5 (ppm): 222.21 (C7), 164.35 (C4), 152.08 (C3), 125.16 (C6), 97.80 (C5), 59.09(C2), 14.50 (C1). HRMS (ESI) mlz calculated for C7H6N2O3S2K2+H308.9 172, found 308.9171. Formula is confirmed as C7H6N20352K2.

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 466 - 475
[2]Patent: WO2016/81522,2016,A1 .Location in patent: Paragraph 00284; 00285, 00291

38
[ 6629-04-5 ]
[ 78-39-7 ]
[ 36980-62-8 ]

Reference： [1]Journal of Organic Chemistry,2007,vol. 72,p. 466 - 475

40
[ 6629-04-5 ]
[ 431-03-8 ]
4,5-dimethyl-1-ethoxycarbonyl-5-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carbonitrile [ No CAS ]

Reference： [1]Australian Journal of Chemistry,2005,vol. 58,p. 882 - 890

41
[ 6629-04-5 ]
[ 888704-22-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404

42
[ 6629-04-5 ]
(E)-ethyl [2-cyano-3-(n-butylamino)acryloyl]carbamate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404

43
[ 6629-04-5 ]
(E)-ethyl [2-cyano-3-anilinoacryloyl]carbamate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404

44
[ 6629-04-5 ]
[ 6275-85-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404
[2]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 3399 - 3404

45
[ 6629-04-5 ]
[ 6275-85-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 1380 - 1388

46
[ 6629-04-5 ]
((Z)-2-Cyano-3-cyclohexylamino-but-2-enoyl)-carbamic acid ethyl ester [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 1380 - 1388

47
[ 6629-04-5 ]
((Z)-2-Cyano-3-phenylamino-but-2-enoyl)-carbamic acid ethyl ester [ No CAS ]

Reference： [1]Chemical and pharmaceutical bulletin,1972,vol. 20,p. 1380 - 1388

48
[ 6629-04-5 ]
[ 1057000-91-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; hydrogenchloride; aniline; sodium nitrite; In water;	Example 7 EX-7A) A mixture of aniline (1; 50 mmol), concentrated HCl (10 mL), and water (50 mL) is cooled to 5 C. Separately, a solution of sodium nitrite (50 mmol) in water (7.2 mL) is cooled to 5 C. and added to the aniline hydrochloride slurry with the addition tube beneath the liquid surface. The temperature is maintained at 5 C. during the addition and for 1 thereafter. This solution of diazotized aniline (EX-7A) is used in the next step. EX-7B) A mixture of cyanoacetylurethane (59 mmol), pyridine (656 mL), ice (216 g) and water (40 mL) is held at 5 C. while the slurry of EX-67A is added over 15 min with stirring. After an additional hour of stirring at 5 C., the orange solid, N-ethoxycarbonyl-2-cyano-2-(N-phenylhydrazo)acetamide (EX-7B is isolated by filtration.

Reference： [1]Patent: US6458952,2002,B1

49
[ 6629-04-5 ]
[ 123-30-8 ]
Ethyl-N-[[[cyano(4-hydroxyphenyl)-hydrazinylidene]-methyl ]-carbonyl]-carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; sodium nitrite; In hydrogenchloride; water; acetic acid;	Ethyl-N-[[[cyano(4-hydroxyphenyl)-hydrazinylidene]-methyl ]-carbonyl]-carbamate STR38 10 g (0.091 mol) of 4-hydroxyaniline are dissolved in 19.7 ml of conc. HCl and 200 ml of glacial acetic acid, and a solution of 6.4 g (0.092 mol) of sodium nitrite in 30 ml of water are added dropwise to the solution at 0-5 C. Stirring is continued until a clear solution has formed, a mixture of 14.3 g (0.092 mol) of cyanoacetylurethane and 21 g (0.25 mol) of sodium acetate is then added, and stirring is continued at 10 C. for 3 h. The reaction mixture is concentrated in vacuo, water is added, and the sol id is filtered off with suction. In this way, 19 g (75%) of product are obtained as a finely-crystalline, yellow powder.

Reference： [1]Patent: US5464837,1995,A

50
[ 6629-04-5 ]
2-(2-aminophenoxy)pyridine [ No CAS ]
ethyl N-[[[cyano(pyridin-4-yloxyphenyl)-hydrazinylidene]methyl]carbonyl]-carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; sodium nitrite; In hydrogenchloride; ethanol; water;	Example 12 Ethyl N-[[[cyano(4-pyridyloxyphenyl)-hydrazinylidene]methyl]carbonyl]-carbamate STR110 16.9 g (0.091 mol) of pyridyloxyaniline are dissolved in 19.7 ml of concentrated HCl and 200 ml of ethanol and, at 0-5 C., a solution of 6.4 g (0.092 mol) of sodium nitrite in 30 ml of water is added dropwise. The mixture is stirred until the solution is clear, and then a mixture of 14.3 g (0.092 mol) of cyanoacetylurethane and 21 g (0.25 mol) of sodium acetate is added and the mixture is left to stir at 10 C. for 3 h. The reaction mixture is evaporated in vacuo and stirred with water, and the solid is filtered off with suction. This results in 25 g (78%) of product as a microcrystalline yellow powder.

Reference： [1]Patent: US5114938,1992,A

51
[ 110-91-8 ]
[ 2420-26-0 ]
[ 6629-04-5 ]
[ 74914-21-9 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	(2) 8-chloro-2,4-(3H)-(1)-benzopyrano-(2,3-d)-pyrimidinedione: Dissolve a mixture of 4-chlorosalicylaldehyde (6 g) and N-cyanoacetylurethane (6 g) in a minimum quantity of ethanol at room temperature. Add morpholine (60 mg) and allow the resulting solution to stand at room temperature overnight. Filter and wash the solid with ethanol. This product, after drying, is heated, with stirring, at 165 C. for 21/2 hours. Add ethanol to the solid, filter, wash with ethanol and then with ether. Dry the product to yield 8-chloro-2,4-(3H)-(1)-benzopyrano-(2,3-d)-pyrimidinedione.

Reference： [1]Patent: US4272535,1981,A

52
[ 110-91-8 ]
[ 6629-04-5 ]
[ 74901-08-9 ]
[ 74901-09-0 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol;	A(1) 7-Hydroxymethyl-2,4-(3H)-(1)-Benzopyrano-(2,3-d)-Pyrimidinedione: To a warmed and stirred solution containing 5-hydroxy methylsalicylaldehyde (46 g) and N-cyanoacetylurethane (48 g) in absolute ethanol, add morpholine (0.5 ml) and reflux the resulting solution for 4 hours. After cooling, filter, ethanol wash and dry the product to yield 7-hydroxymethyl-2,4-(3H)-(1)-benzopyrano-(2,3-d)-pyrimidinedione.

Reference： [1]Patent: US4272535,1981,A

53
[ 6629-04-5 ]
[ 116983-47-2 ]
ethyl N-((7-chloro-2,3-dihydro-2-methyl-4-benzofuranylhydrazono)cyanoacetyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; hydrogenchloride; sodium nitrite; In water;	A mixture of 9.18 g of 32A, 10 mL of 12N hydrochloric acid and 10 mL of water was heated on a steam bath for 1 hour, then 10 mL of water was added and the mixture was stirred at room temperature overnight. Then 30 mL of water was added, the mixture was cooled to 0 C. and stirred while a solution of 3.45 g of sodium nitrite in 10 mL of water was added dropwise over 15 minutes, then was stirred for 1 hour at 0 C. The resulting mixture was added slowly to a stirred mixture of 7.8 g of N-cyanoacetylurethane, 35 mL of pyridine and 900 mL of water, at 0 C. The resulting mixture was stirred at 0 C. for 1.5 hours, and filtered. The collected solid phase was washed with water, dried under reduced pressure and recrystallized from acetone/petroleum ether to give ethyl N-((7-chloro-2,3-dihydro-2-methyl- 4-benzofuranylhydrazono)cyanoacetyl)carbamate (32B), as a solid, m.p.: 175-177 C. (with decomposition).

Reference： [1]Patent: US4881967,1989,A

54
[ 6629-04-5 ]
4-amino-α-(4-chlorophenyl)-2-methoxybenzeneacetonitrile [ No CAS ]
ethyl [2-[[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]hydrazono]-2-cyanoacetyl]carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium acetate; acetic acid; sodium nitrite; In methanol; chloroform; water;	To a stirred and cooled (5-10C) mixture of 5.6 parts of 4-amino-alpha-(4-chlorophenyl)-2-methoxybenzeneacetonitrile, 6.2 parts of concentrated hydrochloric acid and 50 parts of acetic acid is added dropwise, during a 15 minutes period, a solution of 1.25 parts of sodium nitrite in 10 parts of water at about 10C. Upon completion, the whole is stirred for 60 minutes and then 3.6 parts of anhydrous sodium acetate and 2.8 parts of ethyl (2-cyanoacetyl)carbamate are added and stirring is continued for 2 hours at room temperature. The reaction mixture is poured into 250 parts of water. The product is filtered off, washed with water and dissolved in a mixture of trichloromethane and methanol (90:10 by volume). The organic layer is dried, filtered and evaporated. The residue is purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated in vacuo , yielding ethyl [2-[[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]hydrazono]-2-cyanoacetyl]carbamate.
	With hydrogenchloride; sodium acetate; acetic acid; sodium nitrite; In methanol; chloroform; water;	To a stirred and cooled (5-10 C.) mixture of 5.6 parts of 4-amino-alpha-(4-chlorophenyl)-2-methoxybenzeneacetonitrile, 6.2 parts of concentrated hydrochloric acid and 50 parts of acetic acid is added dropwise, during a 15 minutes period, a solution of 1.25 parts of sodium nitrite in 10 parts of water at about 10 C. Upon completion, the whole is stirred for 60 minutes and then 3.6 parts of anhydrous sodium acetate and 2.8 parts of ethyl (2-cyanoacetyl)carbamate are added and stirring is continued for 2 hours at room temperature. The reaction mixture is poured into 250 parts of water. The product is filtered off, washed with water and dissolved in a mixture of trichloromethane and methanol (90:10 by volume). The organic layer is dried, filtered and evaporated. The residue is purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated in vacuo, yielding ethyl [2-[[4-[(4-chlorophenyl)cyanomethyl]-3-methoxyphenyl]hydrazono]-2-cyanoacetyl]carbamate.

Reference： [1]Patent: EP232932,1991,B1
[2]Patent: US4767760,1988,A

55
[ 6629-04-5 ]
C₁₃H₁₁Cl₂N₄O₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]
(2-cyano-2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In water; at 0℃; for 0.5h;	A suspension of 5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenylamine (24) (134 mg, 0.42 mmol) in water (5.6 mL) was treated with concentrated hydrochloric acid (2.8 mL). The reaction mixture was cooled to 00C and then was treated with a solution of sodium nitrate (36.5 mg, 0.529 mmol) in water (0.2 mL) under the surface of the reaction mixture followed by a water (0.2 mL) rinse. The reaction mixture was stirred at 00C for 30 min, and a solution formed. In a separate flask, equipped with a magnetic stirrer, was added N-cyanoacetylurethane (73 mg, 0.46 mol), water (9.4 mL) and pyridine (2.8 mL). This reaction mixture was cooled to 00C and the solution from the first reaction was quickly filtered and poured into the second reaction mixture. An orange precipitate formed and the suspension was stirred at 00C for 30 min. The solid was filtered and rinsed with water followed by petroleum ether. The solid was dried in a vacuum oven overnight at 800C to afford 2-cyano-2-{ [3,5-dichloro-4-(5-isopropyl-6-oxo-l,6-dihydro-pyridazin-3-yloxy)- phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (30) (156 mg, 76%) as an orange solid; EI(+)-HRMS m/z calcd for Ci9Hi8Cl2N6O5 (M+H) 481.0789, found 481.0790. Molecular Weight =481.2985; Exact Mass =480.0716

Reference： [1]Patent: WO2007/9913,2007,A1 .Location in patent: Page/Page column 89

56
[ 6629-04-5 ]
C₁₄H₁₃Cl₂N₄O₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]
(2-cyano-2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In water; acetic acid; at 5 - 10℃; for 0.5h;	A mixture of 6-(4-amino-2,6-dichloro-phenoxy)-4-isopropyl-2-methyl-2H-pyridazin-3-one (67) (1O g, 30.47 mmol) in glacial acetic acid (60 mL) and concentrated hydrochloric acid (9.06 mL) cooled to 5-100C was treated dropwise with a solution of sodium nitrite (2.3 g, 32.3 mmol) in water (6 mL). The reaction was stirred at 5-100C for 30 min. At this time, EPO <DP n="119"/>the reaction was treated with N-cyanoacetylurethane (5.34 g, 33.52 mmol) followed by a solution of sodium acetate (7.5 g, 91.41 mmol) in water (22.5 mL). The reaction was stirred at 5-100C for 30 min and then was diluted with water (50 mL). The resulting solids were collected by filtration, washed with a 1:1 mixture of glacial acetic acid:water (40 mL) followed by water (2 x 60 mL), dried under house vacuum, and then dried under vacuum at 500C to afford (2-cyano-2-{ [3,5-dichloro-4-(5-isopropyl-l-methyl-6-oxo-l,6-dihydro- pyridazin-3-yloxy)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester (68) (15.04 g, 95%) as an orange solid; ES(+)-LRMS for C20H20Cl2N6O5 (M+H)+ at m/z = 495. Exact Mass = 494.0872; Molecular Weight = 495.33.

Reference： [1]Patent: WO2007/9913,2007,A1 .Location in patent: Page/Page column 117-118

57
[ 6629-04-5 ]
C₁₃H₁₁Cl₂N₄OS⁽¹⁺⁾*Cl^(1-) [ No CAS ]
(2-cyano-2-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In water; at 0℃; for 1h;	A mixture of 6-(4-amino-2,6-dichloro-phenylsuhcanyl)-4-isopropyl-2H-pyridazin-3-one (85) (3.40 g, 10.4 mmol) in water (135 mL) and concentrated hydrochloric acid (68 mL) cooled to 00C was treated with a solution of sodium nitrite (853 mg, 12.36 mmol) in water (7.0 mL) via Pasteur pipette under the surface of the reaction mixture. This was followed by a EPO <DP n="131"/>water rinse (1.0 mL) of the Pasteur pipette. The resulting yellow mixture was stirred at 00C for 30 min. More concentrated hydrochloric acid (7.0 mL) was added. The reaction was stirred at 00C for an additional 1.3 h. The solids were removed by filtration through filter paper and were rinsed with water. The clear, yellow diazonium salt solution of the filtrate was quickly poured into a solution of cyanoacetylurethane (1.77 g, 11.33 mmol), pyridine (75 mL) and water (204 mL) cooled to 00C. Upon mixing, orange-red solids immediately formed. This mixture was stirred at 00C for 1 h. At this time, the solids were collected by filtration through filter paper. The solids were washed with water, air-dried under house vacuum for 2 h, and then dried under vacuum to afford (2-cyano-2-{ [3,5-dichloro-4-(5- isopropyl-6-oxo- 1 ,6-dihydro-pyridazin-3-ylsulfanyi)-phenyi] -hydrazono } -acetyl)-carbamic acid ethyl ester (86) (2.98 g, 58%) as an orange solid; ES(+)-HRMS m/e calcd for Ci9Hi8Cl2N6O4S (M+H)+ 497.0560, found 497.0559. Exact Mass = 496.0487; Molecular weight = 497.36

Reference： [1]Patent: WO2007/9913,2007,A1 .Location in patent: Page/Page column 129-130

58
[ 6629-04-5 ]
C₁₅H₁₅Cl₂N₄O⁽¹⁺⁾*Cl^(1-) [ No CAS ]
(2-cyano-2-[3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-ylmethyl)-phenyl]-hydrazono}-acetyl)-carbamic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; In water; at 0℃; for 0.5h;	A mixture of 6-(4-amino-2,6-dichloro-benzyl)-4-isopropyl-2-methyl-2H-pyridazin-3-one(94) (148 mg, 0.45 mmol) in water (6 mL) and concentrated hydrochloric acid (3 mL) cooled to 00C was treated with a solution of sodium nitrite (37.3 mg, 0.54 mmol) in water(0.5 mL) via Pasteur pipette under the surface of the reaction mixture. This was followed by a water rinse (0.5 mL) of the Pasteur pipette. The resulting pale yellow solution was stirred at 00C for 45 min. At this time, the reaction was filtered through a pad of cotton and was drained directly into a solution of cyanoacetylurethane (77.3 mg, 0.49 mmol), pyridine (3 mL) and water (9 mL) cooled to 00C. Upon mixing, orange-red solids immediately formed. This mixture was stirred at 00C for 30 min. At this time, the solids were collected by filtration through filter paper. The solids were washed with water and petroleum ether, air-dried under house vacuum, and then dried under vacuum to afford (2-cyano-2-{ [3,5- EPO <DP n="139"/>dichloro-4-(5-isopropyl- 1 -methyl-6-oxo- 1 ,6-dihydro-pyridazin-3-ylmethyl)-phenyl] - hydrazonoj-acety^-carbamic acid ethyl ester (95) (192 mg, 86%) as an orange solid; ES- HRMS m/e calcd for C2IH22Cl2N6O4 (M+H)+ 493.1153, found 493.1155. Exact Mass = 492.1080; Molecular weight = 493.3533.

Reference： [1]Patent: WO2007/9913,2007,A1 .Location in patent: Page/Page column 137-138

59
[ 6629-04-5 ]
[ 10199-34-5 ]
[Pt[N(CO₂C₂H₅)C(O)CHCN][P(C₆H₅)3]2] [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2000,vol. 298,p. 84 - 89

60
[ 6629-04-5 ]
[ 10199-34-5 ]
[Pt[N(CO₂C₂H₅)C(O)CHCN][P(C₆H₅)3]2] [ No CAS ]
[PtCl[N(CO₂C₂H₅)C(O)CH₂CN][P(C₆H₅)3]2]*0.5CH₂Cl₂ [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2000,vol. 298,p. 84 - 89
[2]Inorganica Chimica Acta,2000,vol. 298,p. 84 - 89

61
[ 6629-04-5 ]
[ 181886-26-0 ]
[ 339525-68-7 ]

Reference： [1]Journal of Organometallic Chemistry,2001,vol. 620,p. 182 - 189

62
[ 12080-32-9 ]
[ 6629-04-5 ]
[ 603-35-0 ]
[PtCl[N(CO₂C₂H₅)C(O)CH₂CN][P(C₆H₅)3]2]*0.5CH₂Cl₂ [ No CAS ]

Reference： [1]Inorganica Chimica Acta,2000,vol. 298,p. 84 - 89

63
[ 6629-04-5 ]
[ 21626-70-0 ]
C₁₆H₁₉N₅O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		3) Diazotation; A mixture of N-cyanoacetylurethane (26.9 mmol) and 30 g sodium acetat in 900 ml water was stirred gentle at 00C while a solution of diazonium salt was added dropwise during 20 min. The diazonium salt was prepared by adding a solution of 1.4 g sodium nitrit in water to a cooled (O0C) solution (20 mmol) amin and 10 ml cone. HCI in 200 ml water. After stirring the mixture for 15 min 15 g sodium acetate in 40 ml water were added. The whole mixture was left standing overnight, the resulting hydrazone collected, washed repeatedly with water and recrystallized repeatedly from EtOH.; Example 7; 2-[4-(morpholin-4-ylsulfonyl)phenyl]-3,5-dioxo-2,3,4,5-tetrahydro-1 ,2,4-triazine-6- carbonitrile; yield: 338 mg (31 %), yellow powder, mp: >300 0C, 1H-NMR (500 MHz, DMSO-d6): delta 2.49 (t, 4H1 CH2), 3.63 (t, 4H, CH2), 7.84 (dd, 4H, 3J=8.7 Hz1 arom. H). 13C-NMR (125.8 MHz, DMSO-de): delta 45.9 (CH2), 65.3 (CH2), 112.6 (Cq), 123.2 (Cq)1 126.3 (Carom), 128.6 (Carom), 134.2 (Cq)1 143.1 (C=O)1 147.6 (Cq), 155.4 (C=O). ESI MS: 362.2 [M-H]-. Anal, calcd. for C14H13N3O4S: C1 46.28 % H1 3.39 % N1 19.27 %. Found: C, 44.87 % H, 3.66 % N1 19.14 %.

Reference： [1]Patent: WO2008/46657,2008,A1 .Location in patent: Page/Page column 22; 23

64
[ 6629-04-5 ]
[ 99-09-2 ]
[ 52348-80-8 ]

Yield	Reaction Conditions	Operation in experiment
100%		According to Scheme 5 Step 1: To a suspension of nitoaniline (5 g, 36.2 mmol) in concentrated HCl (9 mL) and water (50 mL) at 0 C. was added dropwise over 30 minutes a solution of sodium nitrite (5 g, 72.4 mmol in 200 mL water) the crude orange suspension was filtered at 0 C. and the obtained diazonium salt was added portionwise over 1 hour under vigorous stirring to a suspension of ethyl 2-cyanoacetate (6.22 g, 39.8 mmol) and sodium acetate (21.0 g, 257 mmol) in ethanol (200 mL). The reaction mixture was allowed to rest at 0 C. for 1 h. The mixture was filtered, washed with water then cooled ethanol and dried to afford (Z)-2-cyano-2-(2-(3-nitrophenyl)hydrazono)acetylcarbamate 9(A) (11.0 g, 100%, 75% of purity) as an orange solid. The crude solid was used in the next step without further purification.Rf=0.32 CH2Cl2/MeOH (95/5)LC1: Rt=3.65MS m/z (ES) [M+H]+=306

Reference： [1]Patent: US2010/4246,2010,A1 .Location in patent: Page/Page column 21; 31

65
[ 6629-04-5 ]
[ 102-28-3 ]
[ 1207441-77-7 ]

Yield	Reaction Conditions	Operation in experiment
99%		According to Scheme 7 Step 1: To a suspension of 3-aminophenylacetamide (1.50 g, 9.9 mmol), in concentrated HCl (2.5 mL) and water (11 mL) at 0 C. was added dropwise over 30 min a solution of sodium nitrite (1.38 g, 19.9 mmol) in water (20 mL). The crude orange suspension was stirred at 0 C. and the obtained diazonium salt was added portionwise over 1 hour under vigorous stirring to a suspension made of compound N-cyanoacetylurethane (1.71 g, 10.9 mmol) and sodium acetate (5.82 g, 70.9 mmol) in ethanol (37 mL). The reaction mixture was stirred at 0 C. for 2 h. The brown resulting mixture was successively filtered, washed with water, cooled ethanol, Et2O and dried to afford the hydrazone Ethyl (Z)-2-cyano-2-(2-(3-acetamidophenyl)hydrazono)acetylcarbamate 11(A) (3.18 g, 99%).

Reference： [1]Patent: US2010/4246,2010,A1 .Location in patent: Page/Page column 22; 32-33

66
[ 6629-04-5 ]
[ 5369-16-4 ]
C₁₅H₁₈N₄O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1488 - 1490

67
[ 6629-04-5 ]
[ 98-16-8 ]
[ 118806-30-7 ]