Hydrochloric Acid → 1-{4-[2-Cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-piperidine-4-carboxylic acid

HRID 1712995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712995
[OH-].[Na+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([CH:23]([C:30](=[O:43])[NH:31][C:32]3[S:33][C:34]4[C:39]([N:40]=3)=[CH:38][CH:37]=[C:36]([O:41][CH3:42])[N:35]=4)[CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])C.Cl>O.CO>[CH:25]1([CH2:24][CH:23]([C:20]2[CH:19]=[CH:18][C:17]([S:14]([N:11]3[CH2:12][CH2:13][CH:8]([C:6]([OH:7])=[O:5])[CH2:9][CH2:10]3)(=[O:16])=[O:15])=[CH:22][CH:21]=2)[C:30](=[O:43])[NH:31][C:32]2[S:33][C:34]3[C:39]([N:40]=2)=[CH:38][CH:37]=[C:36]([O:41][CH3:42])[N:35]=3)[CH2:29][CH2:28][CH2:27][CH2:26]1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 866257401-{4-[2-Cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-piperidine-4-carboxylic acid ethyl ester

Produkt 1

HCID 594634831-{4-[2-Cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-piperidine-4-carboxylic acidAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Sodium hydroxide (12 mg, 0.2996 mmol) was dissolved in a minimum amount of water and added to a solution of title compound F, 1-{4-[2-Cyclopentyl-1-(5-methoxy-thiazolo[5,4-b]pyridin-2-ylcarbamoyl)-ethyl]-benzenesulfonyl}-piperidine-4-carboxylic acid ethyl ester (90 mg, 0.1498 mmol) in methanol. The reaction was stirred at room temperature overnight, poured into 1N hydrochloric acid, and extracted with ethyl acetate. Extracts were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated to afford the title compound as a yellow foam (63 mg, 73%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.05-1.16 (m, 2 H) 1.36-1.47 (m, 2 H) 1.49-1.61 (m, 5 H) 1.66-1.72 (m, 3 H) 1.75 (s, 1 H) 1.78-1.80 (m, 1 H) 1.92-2.02 (m, 1 H) 2.08-2.18 (m, 1 H) 2.40 (t, J=9.85 Hz, 2 H) 3.35 (d, J=11.37 Hz, 2 H) 3.82-3.92 (m, 4 H) 6.74 (d, J=8.59 Hz, 1 H) 7.59-7.67 (m, 4 H) 7.79 (d, J=8.84 Hz, 1 H) LC/MS 573.1 (M+1) 571.4 (M−1) EC50 in primary enzyme assay 7.1 μM

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a984d662b1124a57a9bba4809440b3ab
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795257B2

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