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113994-41-5

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Basic Information

Molecular Structure:
CAS No.:	113994-41-5
Name:	Dehydro Amlodipine (Amlodipine Impurity D)
Article Data:	13

Formula:	C20H23 Cl N2 O5
Molecular Weight:	406.866
Synonyms:	2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl Ester;3-Ethyl 5-Methyl Ester 2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methylpyridine-3,5-dicarboxylate;Amlodipine Impurity D;Dehydro Amlodipine (Amlodipine Impurity D);2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl Ester Oxalate;Dehydro Amlodipine Oxalate
Density:	1.241±0.06 g/cm3(Predicted)
Melting Point:	106-108°C
Boiling Point:	517.9±50.0 °C(Predicted)
PSA:	100.74000
LogP:	3.84930

Synthetic route

: 2-[2-(phthalimido)ethoxymethyl]-3-ethoxycarbonyl-4-(o-chlorophenyl)-5-methoxycarbonyl-6-methylpyridine

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

Conditions	Yield
With hydrazine hydrate In ethanol at 20℃; for 20h;	98%
With hydrazine In methanol; toluene at 20℃; for 4h;	61%

: 103129-81-3
(R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

Conditions	Yield
With calcium hypochlorite In water; ethyl acetate at 20 - 30℃; Reagent/catalyst; Temperature; Solvent;	93.4%

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

Conditions	Yield
Stage #1: 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine With hydrogenchloride In water Stage #2: With nickel In water at 20℃; for 6h;	73.2%
With potassium permanganate In 1,4-dioxane; water for 16h; Ambient temperature;
With potassium superoxide In dimethyl sulfoxide at 37℃; for 5h; Kinetics;

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

: C4H9N2O2*ClH

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

Conditions	Yield
With Britton-Robinson buffer In water; N,N-dimethyl-formamide at 37℃; pH=7.4; Kinetics;

: 88150-62-3
4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-2-[2-phthalimidoethoxymethyl]-1,4-dihydropyridine

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / Pb(OAc)4 / CH2Cl2; acetic acid / 19 h / 20 °C 2: 98 percent / hydrazine monohydrate / aq. ethanol / 20 h / 20 °C View Scheme

: 103129-82-4
amlodipine

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

Conditions	Yield
With human P450 enzyme CYP3A4; NADPH In aq. phosphate buffer for 0.216667h; pH=7.4; Enzymatic reaction;

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

A: 4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-2-(carboxymethoxy)methyl-6-methylpyridine

B: 4-(2-chlorophenyl)-5-carboxy-2-(carboxymethoxy)methyl-3-ethoxycarbonyl-6-methylpyridine

C: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

Conditions	Yield
With sodium hypochlorite; octabromotetrakis(2,6-dichlorophenyl)porphyrin Fe(III)Cl; water In acetonitrile at 80℃; for 0.166667h; Microwave irradiation;

: 88150-42-9
2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

A: C16H13NO4

B: C17H16N2O5

C: C20H22N2O5

D: C19H20N2O5

E: C18H19NO5

F: C19H18N2O4

G: C18H18N2O5

H: C17H15NO4

I: 130161-00-1
4-(2-Chloro-phenyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

J: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

Conditions	Yield
In water at 10℃; Irradiation;

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

: 98-79-3
L-Pyroglutamic acid

: amlodipine (S)-(-)-pyroglutamate

Conditions	Yield
In ethyl acetate at 25℃; for 1h;	95.3%
In ethyl acetate at 25℃; for 1h;	95.3%

: 113994-41-5
2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

: 149-87-1
Pyroglutamic acid

: amlodipine pyroglutamate (racemate)

Conditions	Yield
	95.2%

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