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116649-85-5

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Basic Information
CAS No.: 116649-85-5
Name: Ramatroban
Article Data: 2
Molecular Structure:
Molecular Structure of 116649-85-5 (Ramatroban)
Formula: C21H21FN2O4S
Molecular Weight: 416.473
Synonyms: 9H-Carbazole-9-propanoicacid, 3-[[(4-fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-, (R)-;BAY-u3405;Baynas;9H-Carbazole-9-propanoicacid, 3-[[(4-fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-, (3R)-;
Density: 1.43 g/cm3
Melting Point: 134-135°
Boiling Point: 654.7 °C at 760 mmHg
Flash Point: 349.7 °C
Appearance: Crystalline solid.
Hazard Symbols: Xi
Risk Codes: 36/37/38
Safety: 26-36/37/39-45
PSA: 96.78000
LogP: 4.56260
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Synthetic route
118699-38-0

(R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide

116649-85-5

ramatroban

Conditions
ConditionsYield
Stage #1: (R)-N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide With water; sodium hydroxide In isopropyl alcohol at 100℃; for 24h;
Stage #2: With hydrogenchloride In water		79%
107-13-1

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116650-36-3

(R)-4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide

116649-85-5

ramatroban

Conditions
ConditionsYield
With potassium hydroxide; sodium hydride 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h; Yield given. Multistep reaction;
51145-61-0

1,2,3,4-tetrahydrocarbazol-3-one

116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 2.) tetrabutylammonium borohydride, 3.) 2N sulfuric acid / 1.) benzene, reflux, 1 h, 2.) CH2Cl2, -50 deg C to room temperature, 3.) methanol, room temperature, 1 h
2: 1.) 2N NaOH, conc. HCl, 2.) ammonium formiate / 2.) 10percent Pd/C / 1.) methanol, ethyl acetate, 2.) dimethylformamide, reflux, 20 min
3: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature
4: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h
View Scheme
Multi-step reaction with 6 steps
1.1: D-glucose / water / 24 h / 30 °C / Enzymatic reaction
2.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
2.2: 10 h / -25 - -15 °C
3.1: water; triphenylphosphine / 15 h / 65 °C
4.1: triethylamine / dichloromethane / 1 h / 20 °C
5.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
5.2: 1 h / 20 °C
6.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
2.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction
3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 0.5 h / -20 °C / Inert atmosphere
3.2: 10 h / -25 - -15 °C
4.1: water; triphenylphosphine / 15 h / 65 °C
5.1: triethylamine / dichloromethane / 1 h / 20 °C
6.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
6.2: 1 h / 20 °C
7.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme

(3R)-3-(1S-phenylethylamino)-1,2,3,4-tetrahydrocarbazole hydrogensulfate

116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) 2N NaOH, conc. HCl, 2.) ammonium formiate / 2.) 10percent Pd/C / 1.) methanol, ethyl acetate, 2.) dimethylformamide, reflux, 20 min
2: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature
3: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h
View Scheme
116650-33-0

(3R)-2,3,4,9-tetrahydro-1H-carbazol-3-amine

116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature
2: 1.) 80percent sodium hydride (in mineral oil), 2.) 10percent potassium hydroxide / 1.) dimethylformamide, 2 h, room temperature, 2.) isopropanol, reflux, 16 h
View Scheme
Multi-step reaction with 3 steps
1.1: triethylamine / dichloromethane / 1 h / 20 °C
2.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
2.2: 1 h / 20 °C
3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
4746-97-8

cyclohexanedione monoethylene ketal

116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: Candida antarctica Lipase A / tetrahydrofuran / 5 h / 30 °C / Enzymatic reaction
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
7.1: water; triphenylphosphine / 15 h / 65 °C
8.1: triethylamine / dichloromethane / 1 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
9.2: 1 h / 20 °C
10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 10 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: Pseudomonas cepacia lipase / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
7.1: water; triphenylphosphine / 15 h / 65 °C
8.1: triethylamine / dichloromethane / 1 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
9.2: 1 h / 20 °C
10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 10 steps
1.1: magnesium sulfate / dichloromethane / 2 h / 20 °C
1.2: 4 h / 110 °C
2.1: trifluoroacetic acid / acetone / 24 h / 65 °C
3.1: sodium tetrahydroborate / methanol / 1.5 h / 0 - 20 °C / Inert atmosphere
4.1: Candida antarctica lipase B / tetrahydrofuran / 8 h / 30 °C / Enzymatic reaction
5.1: dmap; triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
6.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
7.1: water; triphenylphosphine / 15 h / 65 °C
8.1: triethylamine / dichloromethane / 1 h / 20 °C
9.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
9.2: 1 h / 20 °C
10.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
1374648-17-5

(S)-2,3,4,9-tetrahydro-1H-carbazol-3-yl methanesulfonate

116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium azide / dimethyl sulfoxide / 24 h / 20 °C
2.1: water; triphenylphosphine / 15 h / 65 °C
3.1: triethylamine / dichloromethane / 1 h / 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
4.2: 1 h / 20 °C
5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 5 steps
1.1: sodium azide / N,N-dimethyl-formamide / 24 h / 70 °C
2.1: water; triphenylphosphine / 15 h / 65 °C
3.1: triethylamine / dichloromethane / 1 h / 20 °C
4.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
4.2: 1 h / 20 °C
5.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
1374648-18-6

(R)-3-azido-2,3,4,9-tetrahydro-1H-carbazole

116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: water; triphenylphosphine / 15 h / 65 °C
2.1: triethylamine / dichloromethane / 1 h / 20 °C
3.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
3.2: 1 h / 20 °C
4.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
116650-12-5

4-fluoro-N-(2,3,4,9-tetrahydro-1H-carbazol-3-yl)benzenesulfonamide

116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydride / N,N-dimethyl-formamide / 20 °C
1.2: 20 °C
2.1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate
3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1.1: chiralpak IC / hexane; isopropyl alcohol / 30 °C / Resolution of racemate
2.1: sodium hydride / N,N-dimethyl-formamide / 0.08 h / 20 °C
2.2: 1 h / 20 °C
3.1: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme

N-[9-(2-cyanoethyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-4-fluorobenzenesulfonamide

116649-85-5

ramatroban

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chiralpak IC / hexane; isopropyl alcohol / 40 °C / Resolution of racemate
2: water; sodium hydroxide / isopropyl alcohol / 24 h / 100 °C
View Scheme
Raw Materials
54621-12-4
349-88-2
4746-97-8
61894-99-3
116650-33-0
100-63-0
51145-61-0
107-13-1
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Specification

1. Introduction of Ramatroban
Ramatroban is an approved human medication for the treatment of allergic rhinitis that has documented activity as an antagonist. The IUPAC Name of it is 3-[(3R)-3-[(4-fluorophenyl)sulfonylamino]-1,2,3,4-tetrahydrocarbazol-9-yl]propanoic acid. What's more, Ramatroban is therefore a useful tool for the elucidation of PGD2/DP2 function in eosinophils, basophils, and other cells of the TH2 cell-type.

2. Properties of Ramatroban
Boiling point: 654.7 °C at 760 mmHg
Flash Point: 349.7 °C
Density: 1.43 g/cm3
Surface Tension: 56 dyne/cm
Enthalpy of Vaporization: 101.32 kJ/mol
Vapour Pressure: 4.94E-18 mmHg at 25°C
XLogP3-AA: 2.9
H-Bond Donor: 2
H-Bond Acceptor: 6

3. Structure Descriptors of Ramatroban
Canonical SMILES: C1CC2=C(CC1NS(=O)(=O)C3=CC=C(C=C3)F)C4=CC=CC=C4N2CCC(=O)O
Isomeric SMILES: C1CC2=C(C[C@@H]1NS(=O)(=O)C3=CC=C(C=C3)F)C4=CC=CC=C4N2CCC(=O)O
InChI: InChI=1S/C21H21FN2O4S/c22-14-5-8-16(9-6-14)29(27,28)23-15-7-10-20-18(13-15)17-3-1-2-4-19(17)24(20)12-11-21(25)26/h1-6,8-9,15,23H,7,10-13H2,(H,25,26)/t15-/m1/s1  
InChIKey: LDXDSHIEDAPSSA-OAHLLOKOSA-N

4. Use of Ramatroban
Ramatroban is used for the treatment of allergic rhinitis as an antagonist of the thromboxane receptor. It is also an antagonist of the DP2 receptor with IC50 values of 100-170 nM. It is more potent at the DP2 receptor than the TP receptor by 4-5 fold. It is therefore a useful tool for the elucidation of PGD2/DP2 function in eosinophils, basophils, and other cells of the TH2 cell-type.