5699-40-1

Usage

Uses

Used in Pharmaceutical Industry:
N-ACETYLGUANIDINE is used as an intermediate for the synthesis of various pharmaceutical compounds. Its application reason lies in its ability to be a part of the preparation process for novel series of amino-protected 6-alkyl-, 6-aryl-, 6-heteroaryl-, and 5,6-fused-cycloalkane 4-trifluoromethyl-2-acetylaminopyrimidines.
Used in Chemical Synthesis:
In the field of chemical synthesis, N-ACETYLGUANIDINE serves as a key component in creating new series of protected 6-alkyland 6-aryl-2-acetylamino-4(3H)-pyrimidinones. Its role is crucial for the development of these compounds, which have potential applications in various sectors.
Used in Research and Development:
N-ACETYLGUANIDINE is also utilized in research and development for the synthesis of 4-[5-(3-fluorophenyl)furan-2-yl]-2-acetylamino-5-methylimidazole and 4-trifluoromethyl-6-(2,2-dimethoxyethyl)-2-acetylaminopyrimidine. These compounds are of interest for their potential properties and applications, which are still being explored and understood.

InChI:InChI=1/C3H7N3O/c1-2(7)6-3(4)5/h1H3,(H4,4,5,6,7)/p+1

Synthetic route

guanidine carbonate + ethyl acetate (141-78-6) → acetylguanidine (5699-40-1)

Conditions	Yield
With sodium In ethanol at 40 - 60℃;	57%

ethanol (64-17-5) + N,N'-diacetyl-guanidine (81256-27-1) → acetylguanidine (5699-40-1)

guanidine nitrate (113-00-8) + ethyl acetate (141-78-6) → acetylguanidine (5699-40-1)

C19H19N3O5 (1610517-96-8) → acetylguanidine (5699-40-1)

Conditions	Yield
With 10 wt% Pd(OH)2 on carbon; hydrogen In tetrahydrofuran; ethanol at 20℃; under 760.051 Torr; for 16h;

acetylguanidine (5699-40-1) + 3-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-1-bromo-butan-2-one (476623-19-5) → acetic acid 3-[7-benzyloxy-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indol-4-yl]-2-oxo-butyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 23℃; for 48h;	95%

tetrafluoroboric acid diethyl ether complex + acetylguanidine (5699-40-1) → acylguanidinium tetrafluoroborate

Conditions	Yield
In methanol at 20℃;	94%

acetylguanidine (5699-40-1) + 1-[1-(benzenesulfonyl)-1H-indol-3-yl]-2-bromoethan-1-one (332135-64-5) → N-{5-[1-(benzenesulfonyl)-1H-indol-3-yl]-1H-imidazol-2-yl}acetamide

Conditions	Yield
In N,N-dimethyl-formamide at 40℃; for 96h;	92%

(E)-1,1,1-Trifluoro-4-methoxy-4-(4-methoxy-phenyl)-but-3-en-2-one + acetylguanidine (5699-40-1) → 4-trifluoromethyl-6-(4-methoxyphenyl)-2-acetylaminopyrimidine (1020541-03-0)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	85%

acetylguanidine (5699-40-1) + 4-(p-bromophenyl)-1,1,1-trifluoro-4-methoxy-3-buten-2-one → 4-trifluoromethyl-6-(4-bromophenyl)-2-acetylaminopyrimidine (1020541-02-9)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	85%

acetylguanidine (5699-40-1) + 1,3-diphenyl-propen-3-one (614-47-1) → N-(4,6-diphenylpyrimidin-2-yl)acetamide (58413-41-5)

Conditions	Yield
Stage #1: 1,3-diphenyl-propen-3-one With sulfur In dimethyl sulfoxide at 20℃; Sealed tube; Stage #2: acetylguanidine In dimethyl sulfoxide at 40℃; for 12h; Sealed tube;	84%

acetylguanidine (5699-40-1) + 1-(4-amino-3,5-dichlorophenyl)-2-bromoethan-1-one (37148-47-3) → N-(4-(4-amino-3,5-dichlorophenyl)-1H-imidazol-2-yl)acetamide

Conditions	Yield
In acetonitrile at 100℃; for 3h;	81%
In acetonitrile at 100℃; for 3h;	81%

(E)-4-(4-Chloro-phenyl)-1,1,1-trifluoro-4-methoxy-but-3-en-2-one + acetylguanidine (5699-40-1) → 4-trifluoromethyl-6-(4-chlorophenyl)-2-acetylaminopyrimidine (1020541-01-8)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	80%

acetylguanidine (5699-40-1) + 4-methoxy-4-phenyl-1,1,1-trifluorobut-3-en-2-one → 4-trifluoromethyl-6-phenyl-2-acetylaminopyrimidine (1020540-98-0)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	80%

acetylguanidine (5699-40-1) + 2-bromo-1-(4-chlorophenyl)-1-propanone (877-37-2) → N-(5-(4-chlorophenyl)-4-methyl-1H-imidazol-2-yl)acetamide

Conditions	Yield
In acetonitrile at 70℃; for 20h;	80%

1-(benzo[1,3]dioxol-5-yl)-2-bromo-2-(6-methylpyridin-2-yl)ethanone (752260-31-4) + acetylguanidine (5699-40-1) → N-[4-(benzo[1,3]dioxol-5-yl)-5-(6-methylpyridin-2-yl)-1H-imidazol-2-yl]acetamide (945244-83-7)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 96h;	79%

acetylguanidine (5699-40-1) + 2-bromo-4'-fluoroacetophenone (403-29-2) → N-(4-(4-fluorophenyl)-1H-imidazol-2-yl)acetamide (910443-44-6)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 0.333333h; Microwave irradiation;	79%
In acetonitrile at 40℃; for 1h; microwave irradiation;

acetylguanidine (5699-40-1) + 4,6,6-trimethoxy-1,1,1-trifluorohex-3-en-2-one (1140485-84-2) → 4-trifluoromethyl-6-(2,2-dimethoxyethyl)-2-acetylaminopyrimidine (1482520-18-2)

Conditions	Yield
In acetonitrile at 85℃; for 24h;	76%

acetylguanidine (5699-40-1) + 1,1,1-trifluoro-4-methoxy-4-(4-methylphenyl)-3-buten-2-one → 4-trifluoromethyl-6-(4-methylphenyl)-2-acetylaminopyrimidine (1020540-99-1)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	72%

acetylguanidine (5699-40-1) + (R,E)-6-(2-bromo-4-fluorophenyl)-3-(1-hydroxyethylidene)piperidine-2,4-dione (1177369-31-1) → (R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one (934344-61-3)

Conditions	Yield
With pyrrolidine In ethanol at 160℃; for 0.166667h; microwave irradiation;	72%

4-(4-biphenyl)-1,1,1-trifluoro-4-methoxybut-3-en-2-one (868662-39-9) + acetylguanidine (5699-40-1) → 4-trifluoromethyl-6-biphenyl-2-acetylaminopyrimidine (1020541-07-4)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	70%

acetylguanidine (5699-40-1) + 2-(4-bromo-3-oxobutyl)isoindoline-1,3-dione (51132-00-4) → N-<5-<2-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)ethyl>-1H-imidazol-2-yl>acetamide (160072-65-1)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 100h;	70%

acetylguanidine (5699-40-1) + α-bromoacetophenone (70-11-1) → 2-amino-4-phenyl-1H-imidazole hemisulfate

Conditions	Yield
Stage #1: acetylguanidine; α-bromoacetophenone Stage #2: With sulfuric acid; water	68%
Stage #1: acetylguanidine; α-bromoacetophenone In acetonitrile at 80℃; for 9h; Stage #2: With sulfuric acid In acetonitrile for 4h; pH=2; Temperature;	16%

acetylguanidine (5699-40-1) + 1,1,1-trifluoro-4-methoxypent-3-en-2-one (135351-20-1, 102145-82-4) → 4-trifluoromethyl-6-methyl-2-acetylaminopyrimidine (1020540-97-9)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	67%

acetylguanidine (5699-40-1) + C19H23BrF2O (1223104-88-8) → C22H28BrF2N3O (1223105-02-9)

Conditions	Yield
With sodium carbonate In acetonitrile for 4h; Reflux;	67%

acetylguanidine (5699-40-1) + 1-[1-(benzenesulfonyl)-1H-indol-3-yl]-2-bromobutan-1-one → N-{5-[1-(benzenesulfonyl)-1H-indol-3-yl]-4-ethyl-1H-imidazol-2-yl}acetamide

Conditions	Yield
In N,N-dimethyl-formamide at 40℃; for 96h;	67%

acetylguanidine (5699-40-1) + α-bromoacetophenone (70-11-1) → N-[1-(2-oxo-2-phenylethyl)-4-phenyl-1H-imidazol-2-yl]acetamide

Conditions	Yield
In acetonitrile at 80℃; for 8h; Temperature; Time; Solvent; Concentration;	65.9%

acetylguanidine (5699-40-1) + α-bromoacetophenone (70-11-1) → N-<4(5)-Phenyl-1H-imidazol-2-yl>acetamide (160041-64-5)

Conditions	Yield
In acetonitrile at 100℃; for 3h;	64%
In acetonitrile at 100℃; for 3h;	64%
In N,N-dimethyl-formamide at 20℃; for 3.5h; Time; Temperature; Solvent; Concentration;	60%
In N,N-dimethyl-formamide at 0 - 20℃; for 15h;	54%

tert-butyl 4-((dimethylamino)methylene)-3,5-dioxopiperidine-1-carboxylate (478623-90-4) + acetylguanidine (5699-40-1) → C9H10N4O2 + 1,1-dimethylethyl 2-(acetylamino)-5,8-dihydro-5-oxo-pyrido[3,4-d]pyrimidine-7(6H)-carboxylate (478628-60-3)

Conditions	Yield
In toluene for 1.5h; Heating / reflux;	A 63% B 11%

2-trifluoroacetyl-1-methoxycycloheptene (881020-28-6) + acetylguanidine (5699-40-1) → 4-trifluoromethyl-6,7,8,9-tetrahydro-5H-cyclohepta[d]-2-acetylaminopyrimidine (1020541-12-1)

Conditions	Yield
With boron trifluoride diethyl etherate In methanol; isopropyl alcohol at 80 - 85℃; for 20h;	62%

acetylguanidine (5699-40-1) + 2-Bromo-1-[(1S,3R)-3-(3-chloro-phenyl)-2,2-dimethyl-cyclopropyl]-propan-1-one → C17H20ClN3O

Conditions	Yield
In DMF (N,N-dimethyl-formamide) for 72h;	61%

C38H52BrN4O10P (877069-01-7) + acetylguanidine (5699-40-1) → C41H56N7O10P

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 120h;	57%

2-ethoxythiocarbonyl-pyrrolidine-1-carboxylic acid benzyl ester (888314-27-0) + acetylguanidine (5699-40-1) → 2-(N'-acetyl-guanidinocarbothioyl)-pyrrolidine-1-carboxylic acid benzyl ester (888314-29-2)

Conditions	Yield
Stage #1: acetylguanidine With sodium hydride In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: 2-ethoxythiocarbonyl-pyrrolidine-1-carboxylic acid benzyl ester In tetrahydrofuran at 0 - 20℃; for 12.5h; Stage #3: With acetic acid In water pH=3;	56%

acetylguanidine (5699-40-1) + 1,1,1-trifluoro-4-(4-fluorophenyl)-4-methoxybut-3-en-2-one → 4-trifluoromethyl-6-(4-fluorophenyl)-2-acetylaminopyrimidine (1020541-00-7)

Conditions	Yield
In acetonitrile at 80 - 85℃; for 24h;	55%

Upstream product

• 64-17-5 ethanol 
• 81256-27-1 N,N'-diacetyl-guanidine 
• 113-00-8 guanidine nitrate 
• 141-78-6 ethyl acetate 
• 81256-27-1 diacetylguanidine 
• 1610517-96-8 C₁₉H₁₉N₃O₅ 

Downstream Products

• 27182-54-3 5-phenyl-1,2,4-thiadiazol-3-amine 
• 57083-86-0 3-Amino-5-pentyl-1,2,4-thiadiazol 
• 189131-47-3 N-(acetylamidino)-N'-(2,3,5-tri-O-benzoyl-β-D-ribosyl)urea 
• 1016543-82-0 N-(4-(3-(1H-1,2,4-triazol-1-yl)-4-(3,4,5-trimethoxybenzoyl)phenyl)-1H-imidazol-2-yl)acetamide 
• 848949-80-4 N-[4-(2-Azido-ethyl)-5-(4-methoxy-phenyl)-1H-imidazol-2-yl]-acetamide 
• 910443-44-6 N-(4-(4-fluorophenyl)-1H-imidazol-2-yl)acetamide 
• 897934-57-5 C₁₂H₁₂BrN₃O 
• 897934-55-3 C₁₂H₁₁N₃O₂ 
• 1020541-01-8 4-trifluoromethyl-6-(4-chlorophenyl)-2-acetylaminopyrimidine 
• 1020540-98-0 4-trifluoromethyl-6-phenyl-2-acetylaminopyrimidine 
• 1020541-04-1 4-trifluoromethyl-6-(4-nitrophenyl)-2-acetylaminopyrimidine 
• 1160587-14-3 N-(4-(4-bromophenyl)-6-(difluoromethyl)pyrimidin-2-yl)acetamide 
• 1160587-01-8 N-(4-(4-bromophenyl)-6-(1-fluoroethyl)pyrimidin-2-yl)acetamide 
• 1189810-38-5 4-(6,7-dihydropyrido[3,2-b]thieno[2,3-d]oxepin-9-yl)-(2-chlorophenyl)-2-acetamino-1H-imidazole 

Relevant academic research and scientific papers

Triophamine, a Unique Diacylguanidine from the Dorid Nudibranch Triopha catalinae (Cooper)

Triophamine (1), a symmetrical diacylguanidine, has been isolated from skin extracts of the dorid nudibranch Triopha catalinae.The proposed structure of 1 was based on interpretation of the mass, IR, UV, 1H NMR, and 13C NMR spectra.It was verified by comparison with diacetylguanidine (3) and by base-catalyzed hydrolysis to guanidine and 2,4-diethyl-4-hexenoic acid (6).

2-Aminoimidazole-based antagonists of the 5-HT6 receptor – A new concept in aminergic GPCR ligand design

A new strategy in the design of aminergic GPCR ligands is proposed – the use of aromatic, heterocyclic basic moieties in place of the evergreen piperazine or alicyclic and aliphatic amines. This hypothesis has been tested using a benchmark series of 5-HT6R antagonists obtained by coupling variously substituted 2-aminoimidazole moieties to the well established 1-benzenesulfonyl-1H-indoles, which served as the ligands cores. The crystallographic studies revealed that upon protonation, the 2-aminoimidazole fragment triggers a resonance driven conformational change leading to a form of higher affinity. This molecular switch may be responsible for the observed differences in 5-HT6R activity of the studied chemotypes with different amine-like fragments. Considering the multiple functionalization sites of the embedded guanidine fragment, diverse libraries were constructed, and the relationships between the structure and activity, metabolic stability, and solubility were established. Compounds from the N-(1H-imidazol-2-yl)acylamide chemotype (10a–z) exhibited high affinity for 5-HT6R and very high selectivity over 5-HT1A, 5-HT2A, 5-HT7 and D2 receptors (negligible binding), which was attributed to their very weak basicity. The lead compound in the series 4-methyl-5-[1-(naphthalene-1-sulfonyl)-1H-indol-3-yl]-1H-imidazol-2-amine (9i) was shown to reverse the cognitive impairment caused by the administration of scopolamine in rats indicating procognitive potential.

Discovery of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine inhibitors of Erk2

The discovery and optimization of a series of tetrahydropyridopyrimidine based extracellular signal-regulated kinase (Erks) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent and selective inhibition of Erk2 and knockdown of phospho-RSK levels in HepG2 cells and tumor xenografts.

Discovery of 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine inhibitors of Erk2

The discovery and optimization of a series of tetrahydropyridopyrimidine based extracellular signal-regulated kinase (Erks) inhibitors discovered via HTS and structure based drug design is reported. The compounds demonstrate potent and selective inhibition of Erk2 and knockdown of phospho-RSK levels in HepG2 cells and tumor xenografts.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.

POLYHYDROXY BENZOIC ACID DERIVATIVES AND THEIR USE AS NEURAMINIDASE INHIBITORS

The present invention is directed to compositions of the formula: wherein: R2 is H, or an alkyl group having 1 to 3 carbon atoms and 0 to 2 hydroxyls; R3 is H, or hydroxyl; R4 is H, or forms a hydrolyzable ester or amide with -C02-; R5 are H, or are taken together to form =NH; and R6 comprises an amine, or a group having 1 to 12 carbon atoms and 1 to 3 amine groups. The invention is also directed to methods of inhibiting the activity of neuraminidase using the compounds of the invention

1-Pyridylmethyl-3-acyl guanidines

1-Acyl-3-pyridyl guanidine and 1-acyl-3-pyridylalkyl guanidine compounds, methods for the treatment of blood pressure disorders, including hypertension, in humans and other mammals.