6638-79-5

Basic information

• Product Name: N,O-Dimethylhydroxylamine hydrochloride
• Synonyms: n-methoxymethylamine hydrochloride;N-METHOXY-N-METHYLAMINE HYDROCHLORIDE;N,O-DIMETHYLHYDROXYAMINE HYDROCHLORIDE;N,O-DIMETHYLHYDROXYLAMINE HCL;N,O-DIMETHYLHYDROXYLAMINE HYDROCHLORID;N,O-DIMETHYLHYDROXYLAMINE HYDROCHLORIDE;O,N-DIMETHYLHYDROXYLAMINE HCL;O,N-DIMETHYLHYDROXYLAMINE HYDROCHLORIDE
• CAS NO: 6638-79-5
• Molecular Formula: C₂H₈NO*Cl
• Molecular Weight: 97.54
• EINECS: 229-642-1
• Product Categories: API intermediates;Amination;Hydroxylamines;Hydroxylamines (N-Substituted);Hydroxylamines (O-Substituted);Synthetic Organic Chemistry;Active Esters/Additives;Coupling;Synthetic Reagents;Aliphatics;Amines
• Mol File: 6638-79-5.mol

Chemical Properties

• Melting Point: 112-115 °C
• Boiling Point: 2.9 °C at 760 mmHg
• Appearance: White to off-white/Crystalline Powder or Crystals
• Density: 1 g/cm3
• Vapor Pressure: 1710mmHg at 25°C
• Storage Temp.: Store at RT.
• Solubility: DMSO, Methanol
• Water Solubility: SOLUBLE
• Sensitive: Hygroscopic
• BRN: 3650353
• CAS DataBase Reference: N,O-Dimethylhydroxylamine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N,O-Dimethylhydroxylamine hydrochloride(6638-79-5)
• EPA Substance Registry System: N,O-Dimethylhydroxylamine hydrochloride(6638-79-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38-36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 6638-79-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N,O-Dimethylhydroxylamine hydrochloride is used as a reagent for the preparation of an inhibitor of the NLS-derived BC peptides, which have potential applications in the development of drugs targeting specific protein-protein interactions.
Used in Organic Synthesis:
N,O-Dimethylhydroxylamine hydrochloride is used as a reagent in the synthesis of 2-acyloxazoles from 2-oxazolemagnesium chloride. This reaction is important for the preparation of various heterocyclic compounds with potential applications in pharmaceuticals and materials science.
Used in Amide Coupling Reactions:
N,O-Dimethylhydroxylamine hydrochloride is used in amide coupling reactions to form Weinreb amides, which are useful intermediates in the synthesis of Weinreb酮. Weinreb酮 is a valuable reagent for the preparation of esters, amides, and other carbonyl compounds in organic synthesis.
Used in the Preparation of N-Methoxy-N-Methyl-3-Oxo-Butyramide:
N,O-Dimethylhydroxylamine hydrochloride is used as a reagent in the preparation of N-methoxy-N-methyl-3-oxo-butyramide from diketene. N,O-Dimethylhydroxylamine hydrochloride can be used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals.

InChI:InChI=1/C2H7NO.ClH/c1-3-4-2;/h3H,1-2H3;1H

Synthetic route

N,0-dimethylhydroxylamine (1117-97-1) → N,O-dimethylhydroxylamine*hydrochloride (6638-79-5)

Conditions	Yield
With hydrogenchloride	37.1 g

4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide (741712-36-7) + 1-bromo-4,5-difluoro-2-methoxybenzene (202865-58-5) → (4-amino-2-ethylsulfanylpyrimidin-5-yl)(2,3-difluoro-6-methoxyphenyl)methanone (741713-37-1) + (4-amino-2-ethylsulfanylpyrimidin-5-yl)(4,5-difluoro-2-methoxyphenyl)methanone (741713-33-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5)

Conditions	Yield
Stage #1: 1-bromo-4,5-difluoro-2-methoxybenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Stage #2: 4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide In tetrahydrofuran; hexane at -78 - -35℃; for 2h;

trimethylaluminum (75-24-1) → N,O-dimethylhydroxylamine*hydrochloride (6638-79-5)

Conditions	Yield
With hydroxylamine hydrochloride In tetrahydrofuran; toluene at 0℃; Inert atmosphere;

N-methoxy-N-methylbenzenesulfonamide → N,O-dimethylhydroxylamine*hydrochloride (6638-79-5)

Conditions	Yield
Stage #1: N-methoxy-N-methylbenzenesulfonamide With iodine; magnesium In methanol for 0.5h; Sonication; Stage #2: With hydrogenchloride In water pH=1;	46%

2-[3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-N-methoxy-N-methyl-acetamide → [3-(4-Bromo-phenyl)-benzo[d]isothiazol-6-yloxy]-acetic acid + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5)

phenylacetic acid (103-82-2) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-2-phenylacetamide (95092-10-7)

Conditions	Yield
With diethyl cyanophosphonate; triethylamine In N,N-dimethyl-formamide 1) -10 deg C, 0.5 h, 2) r.t., 2.5 h;	100%
With sodium hydroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran; water at 20℃; for 3.5h; pH=4.5;	100%
Stage #1: phenylacetic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran for 1h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With trimethylamine In tetrahydrofuran; acetonitrile for 20h;	97%

indole-3-acetic acid (87-51-4) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 2-(1H-indol-3-yl)-N-methoxy-N-methyl-acetamide (132922-37-3)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 1h;	100%
Stage #1: indole-3-acetic acid With 1,1'-carbonyldiimidazole In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	97%
With triethylamine; dicyclohexyl-carbodiimide In dichloromethane for 2h; Ambient temperature;	84%

t-Boc-L-valine (13734-41-3) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → tert-butyl (S)-1-(N-methoxy-N-methylcarbamoyl)-2-methylpropylcarbamate (87694-52-8)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 4℃;	100%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃;	100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	100%

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-(tert-butoxycarbonyl)-L-isoleucine N'-methoxy-N'-methylamide (87694-51-7)

Conditions	Yield
Stage #1: N-(tert-butyloxycarbonyl)-L-isoleucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 0 - 25℃; for 14h; Inert atmosphere;	100%
Stage #1: N-(tert-butyloxycarbonyl)-L-isoleucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 25℃; for 14h; Inert atmosphere;	100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 2h;	91%

N-tert-butoxycarbonyl-L-leucine (13139-15-6) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide (87694-50-6)

Conditions	Yield
Stage #1: N-tert-butoxycarbonyl-L-leucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 0 - 25℃; for 14h; Inert atmosphere;	100%
Stage #1: N-tert-butoxycarbonyl-L-leucine With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.25h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With 4-methyl-morpholine In dichloromethane at 25℃; for 14h; Inert atmosphere;	100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane	100%

L-N-Boc-Ala (15761-38-3) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate (146553-06-2, 87694-49-3)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane	100%
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	100%
With 1,1'-carbonyldiimidazole In dichloromethane for 16h;	99%

cyclohexanone-4-carboxylic acid ethyleneacetal (66500-55-8) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-Methoxy-N-methyl-1,4-dioxaspiro<4.5>decane-8-carboxamide

Conditions	Yield
Stage #1: cyclohexanone-4-carboxylic acid ethyleneacetal With 1,1'-carbonyldiimidazole In dichloromethane for 1.66667h; Large scale; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane for 24.25h; Large scale;	100%
With 1,1'-carbonyldiimidazole 1.) CHCl3, 2.) r.t., 18 h; Yield given. Multistep reaction;
Stage #1: cyclohexanone-4-carboxylic acid ethyleneacetal With 1,1'-carbonyldiimidazole In dichloromethane for 1.33333h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane for 24h;

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + Nα-(t-butyloxycarbonyl)-Nω-(4-methoxy-2,3,6-trimethylbenzenesulphonyl)-L-arginine (102185-38-6) → N-α-(t-butyloxycarbonyl)-N'-ω'-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-L-arginine-N,O-dimethylhydroxyamide (142801-55-6)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	100%
With N-ethyl-N,N-diisopropylamine; HATU In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	93%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 4.5h;	92%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid (128779-47-5) → (R)-α-<<(1,1-dimethylethoxy)carbonyl>amino>-N-methoxy-N-metyl<1,1'-biphenyl>-4-propanamide (162972-36-3)

Conditions	Yield
With 2-(6-chloro-1H-benzotriazole-1-yl)21,1,3,3-tetramethylaminiumhexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane	100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane for 16h; Ambient temperature;	97%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; (2R)-3-(biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]propanoic acid With 4-methyl-morpholine In dichloromethane at -15℃; for 0.0833333h; Inert atmosphere; Stage #2: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -15 - 20℃; for 5.5h; Inert atmosphere;	87%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; Inert atmosphere;	22.7 g

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (9H-fluoren-9-yl)methyl (2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (156939-65-0)

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	98%
Stage #1: N-(fluoren-9-ylmethoxycarbonyl)glycine With trichloroacetonitrile; triphenylphosphine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	89%

Boc-Nle-OH (6404-28-0) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-Methoxy-N-methyl 2(S)-(tert-butoxycarbonylamino) hexanamide (104062-69-3)

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane	100%
Stage #1: Boc-Nle-OH With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -15℃; for 0.5h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at -15 - 20℃; for 17h;	94%
Stage #1: Boc-Nle-OH With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.25h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃;	85%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + Fmoc-Lys(tert-butoxycarbonyl) (71989-26-9) → (S)-N-α-(fluorenylmethyloxycarbonyl)-N-ε-(tert-butyloxycarbonyl)-lysine N-methoxy-N-methylamide (151145-21-0)

Conditions	Yield
Stage #1: Fmoc-Lys(tert-butoxycarbonyl) With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-d6-formamide at 0℃; for 0.5h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 3.5h;	100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide	98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane	96%

2-furancarbonyl chloride (527-69-5) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-2-furancarboxamide (95091-92-2)

Conditions	Yield
With pyridine; sodium carbonate In tetrahydrofuran at 20℃; Inert atmosphere;	100%
With triethylamine In dichloromethane Ambient temperature;	92%
With potassium carbonate In 2-methyltetrahydrofuran; water at 0 - 20℃;	92%

3-methylthenoyl chloride (61341-26-2) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-3-methylthiophene-2-carboxamide (181868-50-8)

Conditions	Yield
With triethylamine In chloroform at 0 - 20℃; Inert atmosphere;	100%
With triethylamine In chloroform at 0 - 20℃;	100%
With pyridine In dichloromethane for 2h; Ambient temperature; Yield given;
With triethylamine In chloroform at 0 - 20℃;	28.8 g

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester (95514-03-7) → (S)-3-(tert-butyldiphenylsilyloxy)-N-methoxy-N,2-dimethylpropanamide (185996-35-4)

Conditions	Yield
With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;	100%
With isopropylmagnesium chloride In tetrahydrofuran at -20 - -5℃;	99%
With trimethylaluminum In dichloromethane; toluene for 4h; Heating;	60%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + 4-fluorobenzoyl chloride (403-43-0) → 4-fluoro-N-methoxy-N-methylbenzamide (116332-54-8)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h;	100%
With triethylamine In dichloromethane	100%
With triethylamine In dichloromethane at 0 - 18℃; for 16.5h; Inert atmosphere;	99%

3-(tert-butyloxycarbonylamino)propionic acid (3303-84-2) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → [2-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (142570-56-7)

Conditions	Yield
Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -15℃; for 0.25h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at -15 - 20℃; for 16h;	100%
Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane	99%
With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -15 - 20℃; Inert atmosphere;	95%

5-methyl-benzofuran-2-carbonyl chloride (90723-52-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → 5-Methyl-benzofuran-2-carboxylic acid methoxy-methyl-amide (194471-27-7)

Conditions	Yield
With triethylamine In dichloromethane for 0.5h; Ambient temperature;	100%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + Heptanoic acid chloride (2528-61-2) → heptanoic acid N,O-dimethylhydroxyamide (104863-66-3)

Conditions	Yield
With pyridine	100%
With pyridine In dichloromethane at 20℃; for 1h;	93%
With TEA In dichloromethane	92%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid (84358-13-4) → tert-butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate (139290-70-3)

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid With triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 0.166667h; Stage #2: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) Stage #3: With hydrogenchloride In water	100%
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 48h;	99%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	99%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + 3-(tert-butyldimethylsilanyloxy)-4,4-dimethyldihydro-2(3H)-furan-2-one (133094-78-7) → (R)-2-(tert-butyldimethylsilyloxy)-4-hydroxy-N-methoxy-N,3,3-trimethylbutanamide (218434-95-8)

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride; 3-(tert-butyldimethylsilanyloxy)-4,4-dimethyldihydro-2(3H)-furan-2-one With isopropylmagnesium chloride In tetrahydrofuran at 0℃; Stage #2: With water In tetrahydrofuran at 0℃; pH=7; aq. phosphate buffer;	100%
With trimethylaluminum In hexane; benzene for 1h; Ambient temperature;	98%

Upstream product

• 1117-97-1 N,0-dimethylhydroxylamine 
• 73850-31-4 C₅H₁₂NO⁽¹⁺⁾ 
• 3622-35-3 benzothiazole-6-carboxylic acid 
• 75-24-1 trimethylaluminum 
• 741712-36-7 4-amino-2-ethylsulfanylpyrimidine-5-carboxylic acid metoxymethylamide 
• 202865-58-5 1-bromo-4,5-difluoro-2-methoxybenzene 

Downstream Products

• 133146-85-7 N-methoxy-N-methyl-3-oxobutanamide 
• 128562-58-3 N-methyl-N-methoxy-3-bromopropionamide 
• 130250-61-2 2-methyl-N-methoxy-N-methylbenzamide 
• 123707-26-6 N,N'-dimethoxy-N,N'-dimethyl urea 
• 104863-67-4 N-methoxy-N-methyltrifluoroacetamide 
• 95092-10-7 N-methoxy-N-methyl-2-phenylacetamide 
• 133776-41-7 anthranilic acid N-methoxy-N-methylamide 
• 115186-37-3 tert-butyl (2S)-2-{[N-methoxy(N-methyl)amino]carbonyl}pyrrolidine-1-carboxylate 
• 87694-52-8 tert-butyl (S)-1-(N-methoxy-N-methylcarbamoyl)-2-methylpropylcarbamate 
• 87694-50-6 N-(tert-butoxycarbonyl)-L-leucine-N'-methoxy-N'-methylamide 
• 146553-06-2 tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate 
• 160238-48-2 (2R,3S,4R)-N-methoxy-5-(4-methoxybenzyl)oxy-N,2,4-trimethyl-3-(triethylsilyl)oxy-pentanamide 
• 102613-04-7 N-methyl-N-methoxyundec-10-enamide 
• 80783-99-9 N-methoxy-N-methylcinnamamide 

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A novel protocol for the deoxyalkoxyamination of alcohols has been developed, using N-alkoxybenzenesulfonimide (NOSI) as both a sulfonyl transfer reagent and an alkoxyamine source, accessing a diverse range of N-alkoxy-N-alkylbenzenesulfonamides with excellent isolated yields. This method is characterized by metal-free reaction, scalability, and waste-balance. Chiral substrates are converted with excellent levels of stereochemical inversion. NOSI could be generated in situ during the reaction as a stable reagent if a three-component one-pot reaction was designed. Exploiting this approach to run intramolecular reactions offered various N-protected isoxazolidines. In addition, valuable O-alkyl hydroxylamines (or isoxazolidines) were obtained through a neutral strategy of desulfonylation of the products.

HIV INTEGRASE INHIBITORS

The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.

Studies on transannulation reactions across a nine-membered ring: The synthesis of natural product-like structures

A series of diverse natural product-like structures have been synthesised by the use of a number of novel transannulation reactions across a cyclononene ring. Transannular cyclisations through oxygen functionality have generated a number of bicyclo[5.3.1]systems containing bridged cyclic ethers and bicyclo[5.2.2]lactones, as well as a tetrahydrofuran-containing bridged analogue of hexacyclinic acid. An unprecedented Bronsted acid mediated transannular cyclisation between proximal carbons generated bicyclo[4.3.0] nonanes which form the core of the pinguisane and austrodorane families of sesquiterpenoids. In all cases the key factor that determined the mode of reactivity was the conformation of the nine-membered ring and the distance between the reacting centres. The Royal Society of Chemistry 2011.

Discovery of [4-amino-2-(1-methanesulfonylpiperidin-4-ylamino)pyrimidin-5- yl](2,3-difluoro-6-methoxyphenyl)methanone (R547), a potent and selective cyclin-dependent kinase inhibitor with significant in vivo antitumor activity

The cyclin-dependent kinases (CDKs) and their cyclin partners are key regulators of the cell cycle. Since deregulation of CDKs is found with high frequency in many human cancer cells, pharmacological inhibition of CDKs with small molecules has the potential to provide an effective strategy for the treatment of cancer. The 2,4-diamino-5-ketopyrimidines 6 reported here represent a novel class of potent and ATP-competitive inhibitors that selectively target the cyclin-dependent kinase family. This diaminopyrimidine core with a substituted 4-piperidine moiety on the C2-amino position and 2-methoxybenzoyl at the C5 position has been identified as the critical structure responsible for the CDK inhibitory activity. Further optimization has led to a good number of analogues that show potent inhibitory activities against CDK1, CDK2, and CDK4 but are inactive against a large panel of serine/threonine and tyrosine kinases (Ki > 10 μM). As one of these representative analogues, compound 39 (R547) has the best CDK inhibitory activities (Ki = 0.001, 0.003, and 0.001 μM for CDK1, CDK2, and CDK4, respectively) and excellent in vitro cellular potency, inhibiting the growth of various human tumor cell lines including an HCT116 cell line (IC50 = 0.08 μM). An X-ray crystal structure of 39 bound to CDK2 has been determined in this study, revealing a binding mode that is consistent with our SAR. Compound 39 demonstrates significant in vivo efficacy in the HCT116 human colorectal tumor xenograft model in nude mice with up to 95% tumor growth inhibition. On the basis of its superior overall profile, 39 was chosen for further evaluation and has progressed into Phase I clinical trial for the treatment of cancer.

METHOD FOR TREATING CHRONIC PAIN USING MEK INHIBITORS

The invention features a method for treating chronic pain using a compound selected from formulae (I), (II)A, (I)B and (I)C.

Benzenesulfonamide derivatives and their use as MEK inhibitors

Benzenesulfonamides of formula (I), in which W is OR1, NR2OR1, NRARB, NR2NRARB, or NR2(CH2)2-4NRARBand the other variables as defined in the claims, are inhibitors of MEK and are effective in the treatment of proliferative diseases, cancer, stroke, heart failure, xenograft rejection, arthritis, cystic fibrosis, hepatomegaly, cardiomegaly, Alzheimer's disease, complications of diabetes, septic shock, and viral infection.

Heteroaromate OSC inhibitors

The present invention relates to heteroaromate OSC inhibitors. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with 2,3-oxidosqualene-lanosterol cyclase such as hypercholesterolemia, hyperlipemia, arteriosclerosis, vascular diseases, mycoses, gallstones, tumors and/or hyperproliferative disorders, and treatment and/or prophylaxis of impaired glucose tolerance and diabetes.

Multicatalytic protease inhibitors

Disclosed herein are inhibitors of the multicatalytic protease enzyme which are represented by the general formula: STR1 Constituent members and preferred constituent members are disclosed herein. Methodologies for making and using the disclosed compounds are also set forth herein.