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CAS No.: | 133099-07-7 |
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Name: | Darifenacin hydrobromide |
Molecular Structure: | |
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Formula: | C28H30N2O2.HBr |
Molecular Weight: | 507.47 |
Synonyms: | 2-[(3S)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenyl-acetamide hydrobromide;Enablex (TN);3-Pyrrolidineacetamide, 1-(2-(2,3-dihydro-5-benzofuranyl)ethyl)-alpha,alpha-diphenyl-, monohydrobromide, (S)-;Enablex;Darifenacin HBr; |
EINECS: | 603-705-7 |
Melting Point: | 228-230 °C |
Boiling Point: | 614.3 °C at 760 mmHg |
Flash Point: | 325.3 °C |
PSA: | 41.57000 |
LogP: | 5.94630 |
2,3-dihydro-5-(2-bromoethyl)benzofuran
(S)-darifenacin hydrobromide
Conditions | Yield |
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Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium hydroxide; triethylmethylammonium chloride In water; toluene at 100℃; for 15.25h; Stage #2: With hydrogen bromide In water; toluene Product distribution / selectivity; | 93.2% |
Stage #1: (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium hydroxide; triethylmethylammonium chloride In 2-methyltetrahydrofuran; water at 60 - 70℃; Stage #2: 2,3-dihydro-5-(2-bromoethyl)benzofuran In 2-methyltetrahydrofuran; water for 16h; Heating / reflux; Stage #3: With hydrogen bromide In 2-methyltetrahydrofuran; water at 0 - 20℃; for 2h; Product distribution / selectivity; | 90.67% |
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium hydroxide; triethylmethylammonium chloride In water; butanone at 75℃; for 6h; Stage #2: With hydrogen bromide In water; butanone at 0 - 5℃; for 2h; Product distribution / selectivity; | 84.92% |
(S)-2-{1-[2-(benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide
(S)-darifenacin hydrobromide
Conditions | Yield |
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Stage #1: (S)-2-{1-[2-(benzofuran-5-yl)ethyl]-3-pyrrolidinyl}-2,2-diphenylacetamide With hydrogen; acetic acid; palladium 10% on activated carbon at 45 - 50℃; for 6 - 7h; Stage #2: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity; | 85% |
2,3-dihydro-5-(2-bromoethyl)benzofuran
2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide
(S)-darifenacin hydrobromide
Conditions | Yield |
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Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium hydroxide; triethylmethylammonium chloride In water; butanone at 75℃; for 6h; Heating / reflux; Stage #2: With hydrogen bromide In water; butanone | 84.92% |
Stage #1: 2,3-dihydro-5-(2-bromoethyl)benzofuran; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium carbonate In acetonitrile at 70 - 75℃; for 2h; Stage #2: With hydrogen bromide In water; acetone at 0 - 25℃; Product distribution / selectivity; | |
With potassium carbonate In acetonitrile |
2-(2,3-dihydrobenzofuran-5-yl)ethylchloride
(S)-darifenacin hydrobromide
Conditions | Yield |
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Stage #1: 2-(2,3-dihydrobenzofuran-5-yl)ethylchloride; (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate With potassium carbonate In water at 101 - 103℃; for 2.5 - 5h; Stage #2: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity; | 77.2% |
darifenacin
(S)-darifenacin hydrobromide
Conditions | Yield |
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With hydrogen bromide In water; acetone at 0 - 20℃; for 7h; | 75% |
With hydrogen bromide In water; acetone | 65% |
With hydrogen bromide In water; acetone for 1.25 - 2.33333h; Product distribution / selectivity; |
(S)-darifenacin hydrobromide
Conditions | Yield |
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Stage #1: (-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide With potassium hydroxide; tert-Amyl alcohol at 60℃; for 22 - 23h; Heating / reflux; Stage #2: With hydrogen bromide In water; butanone Product distribution / selectivity; | 72% |
Stage #1: (-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide With potassium hydroxide In tert-Amyl alcohol at 60 - 108℃; Stage #2: With water Stage #3: With hydrogen bromide In acetic acid; acetone at 20℃; | 72% |
Stage #1: (-)-3S-(1-carbonitrile-1,1-diphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl)ethyl]pyrrolidine hydrobromide With potassium hydroxide In iso-butanol at 105 - 110℃; for 50h; Stage #2: With hydrogen bromide; acetic acid In acetone for 1h; Stage #3: With sodium hydroxide; water; hydrogen bromide; acetic acid Product distribution / selectivity; more than 3 stages; | 27.5% |
2-(2,3-dihydrobenzofuran-5-yl)ethylchloride
2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide
(S)-darifenacin hydrobromide
Conditions | Yield |
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Stage #1: 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With sodium hydroxide; water In ethyl acetate at 25 - 35℃; for 0.25h; Stage #2: 2-(2,3-dihydrobenzofuran-5-yl)ethylchloride With triethylamine at 95℃; for 15h; Stage #3: With hydrogen bromide In water; acetone for 1h; Product distribution / selectivity; | 70% |
Stage #1: 2-(2,3-dihydrobenzofuran-5-yl)ethylchloride; 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide With potassium carbonate In water at 101 - 103℃; for 2 - 5h; Stage #2: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity; |
2,3-dihydro-5-(2-bromoethyl)benzofuran
(S)-darifenacin hydrobromide
Conditions | Yield |
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Multi-step reaction with 2 steps 1: potassium hydroxide / acetonitrile / 18 h / 40 - 50 °C 2: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile 2: ammonia / methanol / 5 - 7 h / 28 - 45 °C 3: hydrogen bromide / water; acetone / 2.25 - 12 h / 0 - 30 °C View Scheme |
(S)-darifenacin hydrobromide
Conditions | Yield |
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Stage #1: (S)-darifenamine With sodium tetrahydroborate In ethanol at 20℃; for 3h; Stage #2: With water In ethanol Stage #3: With hydrogen bromide In water; butan-1-ol Product distribution / selectivity; |
A
(S)-darifenacin hydrobromide
B
(3R)-2-{1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl}-2,2-diphenylacetamide hydrobromide
Conditions | Yield |
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Purification / work up; Resolution of enanthiomeric mixture; | A 50.8 - 51.8 %Chromat. B 48.0 - 49.0 %Chromat. |
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Product Name: Darifenacin hydrobromide (CAS NO.133099-07-7)
Molecular Formula: C28H30N2O2.HBr
Molecular Weight: 507.47g/mol
Mol File: 133099-07-7.mol
Boiling point: 614.3 °C at 760 mmHg
Flash Point: 325.3 °C
Enthalpy of Vaporization: 91.16 kJ/mol
Vapour Pressure: 5E-15 mmHg at 25°C
H-Bond Donor: 1
H-Bond Acceptor: 3
Structure Descriptors of Darifenacin hydrobromide (CAS NO.133099-07-7):
IUPAC Name: 2-[(3S)-1-[2-(2,3-dihydro-1-benzofuran-5-yl)ethyl]pyrrolidin-3-yl]-2,2-diphenylacetamide hydrobromide
Canonical SMILES: C1CN(CC1C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N)CCC4=CC5=C(C=C4)OCC5.Br
Isomeric SMILES: C1CN(C[C@@H]1C(C2=CC=CC=C2)(C3=CC=CC=C3)C(=O)N)CCC4=CC5=C(C=C4)OCC5.Br
InChI: InChI=1S/C28H30N2O2.BrH/c29-27(31)28(23-7-3-1-4-8-23,24-9-5-2-6-10-24)25-14-17-30(20-25)16-13-21-11-12-26-22(19-21)15-18-32-26;/h1-12,19,25H,13-18,20H2,(H2,29,31);1H/t25-;/m1./s1
InChIKey: UQAVIASOPREUIT-VQIWEWKSSA-N
Product Categories: APIs; Intermediates & Fine Chemicals; Pharmaceuticals
Darifenacin hydrobromide , its CAS NO. is 133099-07-7, the synonyms are (S)-2-{1-(2-(2,3-Dihydrobenzofuran-5-yl)ethyl)-3-pyrrolidnyl}-2,2-diphenylacetamide hydrobromide ; 3-Pyrrolidineacetamide, 1-(2-(2,3-dihydro-5-benzofuranyl)ethyl)-alpha,alpha-diphenyl-, monohydrobromide, (3S)- .