(S)-3-(2-dimethylaminoethyl)-5-[2-oxo-1,3-oxazolidin-4-ylmethyl]-1H-indol-2-carboxylic acid
zolmitriptan
Conditions | Yield |
---|---|
copper(II) oxide In quinoline at 200℃; for 0.333333h; | 90% |
With hydrogenchloride In water at 15 - 18℃; Reflux; Industrial scale; | 1.75 kg |
ethyl (S)-3-(2-(dimethylamino)ethyl)-5-((2-oxazolidin-4-yl)methyl)-1H-indolecarboxylate hydrochloride
zolmitriptan
Conditions | Yield |
---|---|
Stage #1: ethyl (S)-3-(2-(dimethylamino)ethyl)-5-((2-oxazolidin-4-yl)methyl)-1H-indolecarboxylate hydrochloride With water; sodium carbonate for 2 - 2.5h; Heating / reflux; Stage #2: With hydrogenchloride In water at 15 - 18℃; for 3h; Heating / reflux; Stage #3: With sodium hydroxide In water at 15 - 20℃; pH=9.75 - 10; Product distribution / selectivity; | 77% |
formaldehyd
(S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine
zolmitriptan
Conditions | Yield |
---|---|
Stage #1: formaldehyd; (S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine With sodium cyanoborohydride; acetic acid In methanol; water at 5 - 20℃; for 2h; Stage #2: With potassium carbonate In methanol; water pH=10 - 11; Product distribution / selectivity; | 74% |
With sodium cyanoborohydride; acetic acid In methanol Ambient temperature; | 31% |
ethyl 3-(2-dimethylaminoethyl)-5-[(4S)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate
zolmitriptan
Conditions | Yield |
---|---|
Stage #1: ethyl 3-(2-dimethylaminoethyl)-5-[(4S)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate With water; sodium carbonate for 2 - 2.5h; Heating / reflux; Stage #2: With hydrogenchloride In water for 4h; Heating / reflux; Stage #3: With sodium hydroxide In water at 15 - 20℃; pH=9.75 - 10; Product distribution / selectivity; | 45% |
Multi-step reaction with 2 steps 1: sodium carbonate / water / Reflux; Industrial scale 2: hydrogenchloride / water / 15 - 18 °C / Reflux; Industrial scale View Scheme |
4,4-diethoxy-N,N-dimethyl-1-butanamine
zolmitriptan
Conditions | Yield |
---|---|
In water at 90℃; for 3h; Fischer Indole Synthesis; Heating / reflux; | |
With hydrogenchloride In water Reflux; | 62 g |
With hydrogenchloride In water Reflux; Large scale; | 8.2 kg |
4,4-diethoxy-N,N-dimethyl-1-butanamine
(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one
zolmitriptan
Conditions | Yield |
---|---|
Stage #1: (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium metabisulfite; sodium hydroxide In water at 2 - 60℃; for 1.25h; Heating / reflux; Stage #3: 4,4-diethoxy-N,N-dimethyl-1-butanamine With hydrogenchloride; sodium hydroxide more than 3 stages; | |
Stage #1: (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one With hydrogenchloride; sodium nitrite In water at 0℃; for 1.5h; Stage #2: With sodium sulfite In water at 0 - 60℃; Stage #3: 4,4-diethoxy-N,N-dimethyl-1-butanamine | |
Stage #1: (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 0.5h; Stage #2: With sodium sulfite In water at 10℃; for 0.25h; Stage #3: 4,4-diethoxy-N,N-dimethyl-1-butanamine With hydrogenchloride Product distribution / selectivity; more than 3 stages; |
4,4-diethoxy-N,N-dimethyl-1-butanamine
(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one
zolmitriptan
Conditions | Yield |
---|---|
at 90 - 98℃; for 2.5h; Product distribution / selectivity; Heating / reflux; |
Zolmitriptan hydrochloride
zolmitriptan
Conditions | Yield |
---|---|
With potassium carbonate In ethanol; water at 10 - 25℃; for 1.5h; Product distribution / selectivity; |
4-(N,N-dimethylamino)butyraldehyde dimethyl acetal
(S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one
zolmitriptan
Conditions | Yield |
---|---|
Stage #1: 4-(N,N-dimethylamino)butyraldehyde dimethyl acetal; (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one With hydrogenchloride In water at 25 - 90℃; for 5 - 6h; pH=2 - 9; Stage #2: With sodium carbonate In water pH=~ 8 - 9; | |
Stage #1: 4-(N,N-dimethylamino)butyraldehyde dimethyl acetal; (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one In water at 25 - 30℃; pH=9; Stage #2: With hydrogenchloride In water at 85 - 90℃; pH=2; Stage #3: With sodium carbonate In water pH=8 - 9; |
bis(trichloromethyl) carbonate
zolmitriptan
Conditions | Yield |
---|---|
With sodium hydroxide In dichloromethane; water at -15 - 20℃; pH=9 - 11; |
(S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one
zolmitriptan
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / water / -10 - 30 °C 2.1: hydrogenchloride; tin(ll) chloride / water / 4 h / -10 - 5 °C 2.2: pH 8 - 9 3.1: water / 25 - 30 °C / pH 9 3.2: 85 - 90 °C / pH 2 3.3: pH 8 - 9 View Scheme | |
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / water / -5 - 10 °C 1.2: -15 - 10 °C 2.1: hydrogenchloride / isopropyl alcohol / 75 - 90 °C 3.1: hydrogenchloride / water / Reflux View Scheme |
zolmitriptan
zolmitriptan
Conditions | Yield |
---|---|
With sodium tungstate (VI) dihydrate; methanesulfonic acid; dihydrogen peroxide In methanol; water at 50 - 55℃; | 90% |
zolmitriptan
2-(S)-amino-3-[3-(2-dimethylaminoethyl)-1H-indol-5-yl]propan-1-ol
Conditions | Yield |
---|---|
With sodium hydroxide In water | 83% |
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane; 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,4-dioxane at 60℃; Inert atmosphere; Sealed tube; | 45% |
zolmitriptan
Conditions | Yield |
---|---|
With trimethylsilyl bromide; dimethyl sulfoxide for 0.833333h; Ambient temperature; | 35% |
zolmitriptan
Zolmitriptan hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In water at 10℃; for 0.75h; Product distribution / selectivity; NaCl; | |
With hydrogenchloride In water Product distribution / selectivity; NaCl; |
chloroformic acid ethyl ester
zolmitriptan
4-(S)-[3-(2-chloroethyl)-1H-indol-5-ylmethyl]oxazolidin-2-one
Conditions | Yield |
---|---|
In toluene for 8h; Reflux; | 5 g |
oxalic acid
zolmitriptan
Conditions | Yield |
---|---|
In methanol; water |
(1S)-10-camphorsulfonic acid
zolmitriptan
Conditions | Yield |
---|---|
In methanol |
4-chlorobenzaldehyde
zolmitriptan
Conditions | Yield |
---|---|
With triethylsilane; trifluoroacetic acid In dichloromethane at 0 - 23℃; Inert atmosphere; |
Molecular Structure of Zolmitriptan (CAS NO.139264-17-8):
IUPAC Name: (4R)-4-[[3-(2-dimethylaminoethyl)-1H-indol-5-yl]methyl]-1,3-oxazolidin-2-one
Molecular formula: C16H21N3O2
Molecular Weight: 287.36
H bond acceptors: 5
H bond donors: 2
Freely Rotating Bonds: 5
Polar Surface Area: 37.71Å2
Index of Refraction: 1.619
Molar Refractivity: 82.89 cm3
Molar Volume: 236.1 cm3
Surface Tension: 53 dyne/cm
Density: 1.217 g/cm3
Flash Point: 294.5 °C
Enthalpy of Vaporization: 84.66 kJ/mol
Boiling Point: 563.3 °C at 760 mmHg
Vapour Pressure: 1.03E-12 mmHg at 25°C
Melting point: 136-141°C
Appearance: White Crystalline Powder
InChI
InChI=1/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1
Smiles
c12c([nH]cc1CCN(C)C)ccc(c2)C[C@@H]1NC(=O)OC1
Product Categories: Antimigraine; All Inhibitors; Inhibitors; Intermediates & Fine Chemicals; Pharmaceuticals; Zolmitriptan
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
women | TDLo | oral | 6mg/kg/43W-I (6mg/kg) | BEHAVIORAL: HEADACHE | Lancet. Vol. 353, Pg. 378, 1999. |
Hazard Codes: Xi
The Risk Statements information of Zolmitriptan:
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements information of Zolmitriptan:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
Zolmitriptan , with CAS number of 139264-17-8, can be called (S)-4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone ; (S)-4-((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)-2-oxazolidinone ; 2-Oxazolidinone, 4-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)-, (S)- ; 4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinone . The usage of Zolmitriptan is as an serotonin 5HTID-receptor agonist.
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