Potassium Carbonate → (3R)-N-(4'-[(Isopropylamino)sulfonyl]biphenyl-4-yl)quinuclidine-3-carboxamide hydrochloride

HRID 2362762Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2362762
C(=O)([O-])[O-].[K+].[K+].Cl.[N:8]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[C@@H:10]([C:16]([Cl:18])=[O:17])[CH2:9]2.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([S:32]([NH:35][CH:36]([CH3:38])[CH3:37])(=[O:34])=[O:33])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1.O1CCOCC1>CN(C=O)C>[ClH:18].[CH:36]([NH:35][S:32]([C:29]1[CH:30]=[CH:31][C:26]([C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:16]([C@@H:10]3[CH:11]4[CH2:14][CH2:15][N:8]([CH2:13][CH2:12]4)[CH2:9]3)=[O:17])=[CH:25][CH:24]=2)=[CH:27][CH:28]=1)(=[O:34])=[O:33])([CH3:38])[CH3:37]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 57462844(3R)-Quinuclidine-3-carbonyl chloride hydrochlorideHCID 596940904'-Amino-N-isopropylbiphenyl-4-sulfonamide

Produkt 1

HCID 11374690(3R)-N-(4'-[(Isopropylamino)sulfonyl]biphenyl-4-yl)quinuclidine-3-carboxamide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

64.3 mg (0.46 mmol) of potassium carbonate are added to a mixture, prepared under argon, of 65.1 mg (0.31 mmol) of (3R)-quinuclidine-3-carbonyl chloride hydrochloride (Example 5A) and 45.0 mg (0.15 mmol) of 4′-amino-N-isopropylbiphenyl-4-sulfonamide (Example 12A) in 2.2 ml of a 10:1 mixture of dioxane and DMF. After 18 h at 100° C., the reaction mixture is concentrated in vacuo. The residue is dissolved in water and acetonitrile and purified by preparative HPLC. The product fractions are concentrated, mixed with 5 ml of a 2:1 mixture of acetonitrile and 1 N hydrochloric acid, again concentrated and dried under high vacuum. 21 mg (29.2% of theory) of the title compound are obtained. HPLC (Method 1): Rt=3.93 min. MS (ESIpos): m/z=428 (M+H)+.

Aufarbeitung

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in water
  3. customacetonitrile and purified by preparative HPLC
  4. concentrationThe product fractions are concentrated
  5. additionmixed with 5 ml of a 2:1 mixture of acetonitrile and 1 N hydrochloric acid
  6. concentrationagain concentrated
  7. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-08c05077c8154d64a09518c02928c5e4
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691840B2

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