49773-20-8

Basic information

• Product Name: 2-Aminoethylmethyl sulfone
• Synonyms: 2-(Methylsulfonyl)ethaneamine;3-Aminopropane-1-sulfinate;2-Aminoethylmethyl sulfone;2-(methylsulfonyl)ethanamine(SALTDATA: 0.95HCl);2-(methylsulfonyl)ethanamine 0.95HCl;Ethanamine, 2-(methylsulfonyl)- HCL
• CAS NO: 49773-20-8
• Molecular Formula: C₃H₉NO₂S
• Molecular Weight: 180.27
• Product Categories: API intermediates
• Mol File: 49773-20-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 368.5°Cat760mmHg
• Flash Point: 176.7°C
• Appearance: /
• Density: 1.223g/cm³
• Vapor Pressure: 1.27E-05mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 7.02±0.10(Predicted)
• CAS DataBase Reference: 2-Aminoethylmethyl sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Aminoethylmethyl sulfone(49773-20-8)
• EPA Substance Registry System: 2-Aminoethylmethyl sulfone(49773-20-8)

Safety Data

• Hazardous Substances Data: 49773-20-8(Hazardous Substances Data)

Usage

Uses

2-(Methylsulfonyl)ethanamine is useful for the synthesis of potent and selective PI3Kδ inhibitors.

InChI:InChI=1/C8H11NO2S/c9-6-7-12(10,11)8-4-2-1-3-5-8/h1-5H,6-7,9H2

Synthetic route

methanesulfonyl-acetonitrile (2274-42-2) → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
Stage #1: methanesulfonyl-acetonitrile With dimethylsulfide borane complex In tetrahydrofuran at 20 - 40℃; for 14h; Stage #2: With methanol In tetrahydrofuran at 0 - 80℃; for 2h; Reflux;	90%
With dimethylsulfide borane complex In tetrahydrofuran

2-<2-(methylsulfonyl)ethyl>-1H-isoindole-1,3(2H)dione → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
With hydrazine In ethanol; chloroform at 0 - 20℃;	80%

BH3·THF + methanesulfonyl-acetonitrile (2274-42-2) → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
With hydrogenchloride; sodium methylate In tetrahydrofuran; methanol; dichloromethane	77.89%

2-methylsulfonylethyl methanesulfonate (191604-52-1) → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
With ammonia In dichloromethane at 45℃; under 1500.15 Torr; for 3h; Pressure; Temperature; Inert atmosphere;	66.9%

2-chloroethyl methyl sulfone (50890-51-2) → 2-Methanesulfonyl-ethylamine (49773-20-8) + bis-(2-methanesulfonyl-ethyl)-amine

Conditions	Yield
With ammonia

methyl-(2-nitro-ethyl)-sulfone → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
With methanol; nickel Hydrogenation;

(2-aminoethyl)methylsulfide (18542-42-2) + KMnO4 → 2-Methanesulfonyl-ethylamine (49773-20-8)

2-chloroethyl methyl sulfone (50890-51-2) → 2-Methanesulfonyl-ethylamine (49773-20-8) + β.β'-bis-methanesulfonyl-diethylamine

Conditions	Yield
With ammonia

[2-(methylsulfonyl)ethyl]trifluoroacetamide (202197-68-0) → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
Alkaline hydrolysis;

(2-methanesulfonyl-ethyl)-carbamic acid benzyl ester (146698-94-4) → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol

C10H15NO3S → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
With ammonium formate; palladium 10% on activated carbon In methanol

2-(methylsulfonyl)ethyl 4-methylbenzenesulfonate (103275-86-1) → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
With ammonia In diethyl ether at 50℃; for 1h;
With ammonia

N,N-dibenzyl-2-(methylsulfonyl)ethylamine (824938-65-0) → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
With hydrogen; Raney nickel In ethanol

2-(methylsulfonyl)ethylamine hydrochloride (104458-24-4) → 2-Methanesulfonyl-ethylamine (49773-20-8)

Conditions	Yield
With sodium hydroxide In ethanol at 20℃; for 0.5h; Product distribution / selectivity;
With sodium methylate In methanol at 20℃; for 0.25h;

2-Methanesulfonyl-ethylamine (49773-20-8) + C32H37N5O15 → C30H38N2O16S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane for 0.166667h;	98%

2-Methanesulfonyl-ethylamine (49773-20-8) + 6-(thiazol-5-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-4-carboxylic acid → N-(2-(methylsulfonyl)ethyl)-6-(thiazol-5-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-4-carboxamide

Conditions

Yield

Stage #1: 6-(thiazol-5-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-Methanesulfonyl-ethylamine In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;

98%

1-(5-(methoxycarbonyl)-4-{[2-(trifluoromethyl)benzyl]oxy}thien-2-yl)-1H-benzimidazole-5-carboxylic acid (660870-46-2) + 2-Methanesulfonyl-ethylamine (49773-20-8) → methyl 5-[5-({[2-(methylsulfonyl)ethyl]amino}carbonyl)-1H-benzimidazol-1-yl]-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In DMF (N,N-dimethyl-formamide) for 12h;	95%

2-Methanesulfonyl-ethylamine (49773-20-8) + toluene-4-sulfonic acid (104-15-4) + 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5) → lapatinib ditosylate (388082-78-8)

Conditions	Yield
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde In methanol; dichloromethane at 20℃; Stage #2: With hydrogen In methanol; dichloromethane Inert atmosphere; Stage #3: toluene-4-sulfonic acid In methanol; dichloromethane	93%

2-Methanesulfonyl-ethylamine (49773-20-8) + toluene-4-sulfonic acid (104-15-4) + 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5) → ({5-[4-({3-chloro-4-[(3-fluorophenyl)methoxy]phenyl}amino)quinazolin-6-yl]furan-2-yl}methyl) [2-(methylsulfonyl)ethyl]azanium 4-methylbenzenesulfonate

Conditions	Yield
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde In methanol; dichloromethane at 20℃; Stage #2: With hydrogen In methanol; dichloromethane Inert atmosphere; Stage #3: toluene-4-sulfonic acid In methanol; dichloromethane; toluene Product distribution / selectivity;	93%

6-(2,4-difluorophenoxy)-8-methyl-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one (449808-50-8) + 2-Methanesulfonyl-ethylamine (49773-20-8) → 2-(2'-methylsulfonylethylamino)-6-(2,4-difluorophenoxy)-8-methylpyrido[2,3-d]pyrimidin-7(8H)-one (1280218-18-9)

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 65℃; for 0.5h;	92%

2-Methanesulfonyl-ethylamine (49773-20-8) + C23H24N4O14 → C24H30N2O16S

Conditions	Yield
for 0.0833333h;	92%

[(4-{[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]amino}quinazolin-5-yl)oxy]acetic acid sodium salt (871018-54-1) + 2-Methanesulfonyl-ethylamine (49773-20-8) → 2-{4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-quinazolin-5-yloxy}-N-(2-methanesulfonyl-ethyl)-acetamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In DMF (N,N-dimethyl-formamide) at 65℃; for 18h;	89%

2-Methanesulfonyl-ethylamine (49773-20-8) + 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde tosylate + toluene-4-sulfonic acid (104-15-4) → lapatinib ditosylate (388082-78-8)

Conditions

Yield

Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-[3-chloro-4-(3-fluorobenzyloxy)-anilino]-6-quinazolinyl)-furan-2-carbaldehyde tosylate With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; isopropyl alcohol for 1h; Industrial scale; Stage #2: With sodium tris(acetoxy)borohydride; isopropyl alcohol In tetrahydrofuran at 20℃; for 1.66667h; Industrial scale; Stage #3: toluene-4-sulfonic acid Industrial scale; Further stages;

88%

2-Methanesulfonyl-ethylamine (49773-20-8) + (S)-phenyl-N-(4-((3-chloro-4-fluorophenyl)amino)-7-((tetrahydrofuran-3-yl)oxy)quinazolin-6-yl)carbamate → (S)-1-(4-(3-chloro-4-fluorophenylamino)-7-(tetrahydrofuran-3-yloxy)quinazolin-6-yl)-3-(2-(methylsulfonyl)ethyl)urea

Conditions	Yield
In tetrahydrofuran at 70℃; for 4h;	86%

2-Methanesulfonyl-ethylamine (49773-20-8) + 2-(3,4,5-trimethoxyphenyl)-5-methyloxazole-4-carboxylic acid (1198279-82-1) → 2-(3,4,5-dimethoxyphenyl)-5-methyl-N-(2-(methylsulfonyl)ethyl)oxazole-4-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;	86%

2-Methanesulfonyl-ethylamine (49773-20-8) + (3aR,4R,5R,7S,8S,9R,9aS,12R)-8-hydroxy-4,7,9,12-tetramethyl-3-oxo-7-vinyldecahydro-4,9a-propanocyclopenta[8]annulen-5-yl 2-iodoacetate (31716-03-7) → 14-O-(hexadecyl)aminoacetylmutilin

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 75℃; for 4h;	85.31%

2-Methanesulfonyl-ethylamine (49773-20-8) + 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde (231278-84-5) → lapatanib (231277-92-2)

Conditions	Yield
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde In methanol; dichloromethane at 20℃; Stage #2: With hydrogen In methanol; dichloromethane Inert atmosphere;	85%
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine Stage #2: With toluene-4-sulfonic acid	80%
Stage #1: 2-Methanesulfonyl-ethylamine; 5-(4-(3-chloro-4-(3-fluorobenzyloxy)phenylamino)quinazolin-6-yl)furan-2-carbaldehyde With triethylamine In tetrahydrofuran; methanol for 3h; Stage #2: With methanol; sodium tetrahydroborate In tetrahydrofuran at 20℃; Cooling with ice;	70%

2-Methanesulfonyl-ethylamine (49773-20-8) + 2-(3,4-dimethoxyphenyl)-5-methyloxazole-4-carboxylic acid → 2-(3,4-dimethoxyphenyl)-5-methyl-N-(2-(methylsulfonyl)ethyl)oxazole-4-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃;	84%

Upstream product

• 50890-51-2 2-chloroethyl methyl sulfone 
• 2274-42-2 methanesulfonyl-acetonitrile 
• 191604-52-1 2-methylsulfonylethyl methanesulfonate 
• 104458-24-4 2-(methylsulfonyl)ethylamine hydrochloride 
• 824938-65-0 N,N-dibenzyl-2-(methylsulfonyl)ethylamine 
• 103275-86-1 2-(methylsulfonyl)ethyl 4-methylbenzenesulfonate 
• 146698-94-4 (2-methanesulfonyl-ethyl)-carbamic acid benzyl ester 
• 202197-68-0 [2-(methylsulfonyl)ethyl]trifluoroacetamide 
• 18542-42-2 (2-aminoethyl)methylsulfide 

Downstream Products

• 1135150-68-3 C₂₇H₂₄ClFN₄O₄S₂ 
• 1135150-80-9 C₂₇H₂₄ClFN₄O₃S₃ 
• 1135150-78-5 C₂₇H₂₄ClFN₄O₄S₂ 
• 1135150-75-2 C₂₇H₂₅ClFN₅O₃S₂ 
• 1135150-85-4 C₂₇H₂₅ClFN₅O₃S₂ 
• 1135150-69-4 C₂₇H₂₄ClFN₄O₄S₂ 
• 1135150-71-8 C₂₇H₂₄ClFN₄O₃S₃ 
• 1135150-81-0 C₂₇H₂₄ClFN₄O₃S₃ 
• 104458-24-4 2-(methylsulfonyl)ethylamine hydrochloride 
• 1255501-25-7 2-aminoethyl methyl sulfone-p-toluenesulfonate 
• 1595285-81-6 (E)-N-(4-((3-chloro-4-fluorophenyl)amino)thieno[2,3-d]pyrimidin-6-yl)-4-((2-(methylsulfonyl)ethyl)amino)but-2-enamide 
• 231277-94-4 (4-phenoxyphenyl)-(7-((4-(2-methanesulphonyl)ethylaminomethyl)thiazol-5-yl)-quinolin-4-yl)amine 

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