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Methyl iodide → (R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate

HRID 877747
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 877747
[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]([NH:15][NH2:16])=[O:14])[CH:12]=[C:6]2[C:5]=1[NH:17][C@@H:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C:19]1([CH3:32])[CH3:31])(=[O:3])[NH2:2].N1([C:38](N2C=CN=C2)=[S:39])C=CN=C1.[CH2:45](N(CC)CC)C.IC>O1CCCC1>[C:1]([C:4]1[CH:9]=[N:8][N:7]2[CH:10]=[C:11]([C:13]3[O:14][C:45]([S:39][CH3:38])=[N:16][N:15]=3)[CH:12]=[C:6]2[C:5]=1[NH:17][C@@H:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C:19]1([CH3:32])[CH3:31])(=[O:3])[NH2:2]
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Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 68291130(R)-tert-butyl 4-((3-carbamoyl-6-(hydrazinecarbonyl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate

Produkt 1

HCID 68350378(R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate
Ausbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (R)-tert-butyl 4-((3-carbamoyl-6-(hydrazinecarbonyl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate (380 mg, 0.853 mmol) and di(1H-imidazol-1-yl)methanethione (175 mg, 0.981 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 10 min then heated to reflux for 100 min. After cooling to room temperature, triethylamine (0.357 mL, 2.56 mmol) and iodomethane (0.107 mL, 1.706 mmol) were added. The resulting mixture was stirred at room temperature for 5 h. The tetrahydrofuran solvent was evaporated in vacuo. The residue was triturated with water. The solid product was collected by filtration to give (R)-tert-butyl 4-((3-carbamoyl-6-(5-(methylthio)-1,3,4-oxadiazol-2-yl)pyrrolo[1,2-b]pyridazin-4-yl)amino)-3,3-dimethylpiperidine-1-carboxylate as white solid (0.404 g, 94% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 10.78 (d, J=8.4 Hz, 1H), 8.10 (d, J=1.8 Hz, 1H), 7.94 (s, 1H), 5.50 (br. s., 2H), 4.01 (dd, J=9.4, 5.8 Hz, 2H), 3.72 (br. s., 1H), 3.18 (br. s., 1H), 2.91 (br. s., 1H), 2.80 (s, 3H), 2.06 (d, J=14.3 Hz, 1H), 1.89-1.75 (m, 1H), 1.49 (s, 9H), 1.12 (s, 3H), 1.05 (s, 3H); MS (ES+) m/z: 502.3 (M+H); LC retention time: 4.241 min (analytical HPLC Method H).

Aufarbeitung

  1. temperaturethen heated
  2. temperatureto reflux for 100 min
  3. customThe tetrahydrofuran solvent was evaporated in vacuo
  4. customThe residue was triturated with water
  5. filtrationThe solid product was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d0e01d80e9544b11ae645ae579867b4d
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08987268B2

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