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Sodium Hydroxide → (R)-4-((1-(tert-butoxycarbonyl)-3,3-dimethylpiperidin-4-yl)amino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylic acid

HRID 877745
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Reaktionsgleichung

Reaktionsgleichung von HRID 877745
[OH-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C@@H:13]([NH:16][C:17]2[C:18]3[N:19]([CH:26]=[C:27]([C:29]([O:31]CC)=[O:30])[CH:28]=3)[N:20]=[CH:21][C:22]=2[C:23](=[O:25])[NH2:24])[C:12]([CH3:35])([CH3:34])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO.O1CCCC1>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][C@@H:13]([NH:16][C:17]2[C:18]3[N:19]([CH:26]=[C:27]([C:29]([OH:31])=[O:30])[CH:28]=3)[N:20]=[CH:21][C:22]=2[C:23](=[O:25])[NH2:24])[C:12]([CH3:35])([CH3:34])[CH2:11]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]
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Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 68350368(R)-ethyl 4-((1-(tert-butoxycarbonyl)-3,3-dimethylpiperidin-4-yl)amino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylate

Produkt 1

HCID 68291940(R)-4-((1-(tert-butoxycarbonyl)-3,3-dimethylpiperidin-4-yl)amino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylic acidAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 2 M aqueous solution of sodium hydroxide (6 mL, 12.00 mmol) was added to a solution of (R)-ethyl 4-((1-(tert-butoxycarbonyl)-3,3-dimethylpiperidin-4-yl)amino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylate (1.187 g, 2.58 mmol) in methanol (11 mL) and tetrahydrofuran (11 mL) at room temperature. The resulting mixture was heated at reflux for 40 min and cooled to room temperature. The organic solvents were evaporated in vacuo. The residue was neutralized to pH 5 with 1 N HCl. The resulting precipitate was collected by filtration to give (R)-4-((1-(tert-butoxycarbonyl)-3,3-dimethylpiperidin-4-yl)amino)-3-carbamoylpyrrolo[1,2-b]pyridazine-6-carboxylic acid as brown solid (1.13 g, 97% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.57 (br. s., 1H), 11.16 (d, J=8.8 Hz, 1H), 8.31 (s, 1H), 8.05 (d, J=1.3 Hz, 1H), 7.23 (s, 1H), 4.12-4.00 (m, 1H), 3.87 (br. s., 1H), 3.56 (d, J=12.8 Hz, 1H), 3.01 (br. s., 2H), 1.91 (dd, J=13.5, 3.2 Hz, 1H), 1.56 (d, J=8.1 Hz, 1H), 1.41 (s, 9H), 0.98 (s, 3H), 0.92 (s, 3H); MS (ES+) m/z: 432.2 (M+H); LC retention time: 3.795 min (analytical HPLC Method H).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 40 min
  3. customThe organic solvents were evaporated in vacuo
  4. filtrationThe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-eb0a972e77bf47dcac7d2685a08e766d
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987268B2

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