2-Dimethylaminopyridine → Methyl 5-chloro-1-((4-((dimethylamino)methyl)thiazol-2-yl)carbamoyl)spiro[indoline-3,3'-pyrrolidine]-1'-carboxylate

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[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][NH:8][C:5]2=[CH:6][CH:7]=1.[CH3:19][N:20]([CH2:22][C:23]1[N:24]=[C:25]([NH2:28])[S:26][CH:27]=1)[CH3:21].[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30].CN(C1C=CC=CN=1)C>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][CH3:18])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:29](=[O:30])[NH:28][C:25]3[S:26][CH:27]=[C:23]([CH2:22][N:20]([CH3:21])[CH3:19])[N:24]=3)[C:5]2=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 45 °C

Versuchsvorschrift

The methyl 5-chlorospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (20 mg, 0.076 mmol) obtained in Step 1 of Example 89 was dissolved in tetrahydrofuran (1.0 mL). Thereafter, the 4-((dimethylamino)methyl)thiazole-2-amine (12 mg, 0.076 mmol) synthesized by a method described in the known methods (International Publication WO2008/086047 etc.) or a method similar thereto, carbonyldiimidazole (24 mg, 0.152 mmol), and dimethylaminopyridine (1.0 mg, 0.008 mmol) were added to the above obtained solution, and the thus obtained mixture was then stirred at 45° C. for 12 hours. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by silica gel column chromatography (chloroform:methanol=10:1) to obtain the captioned compound (12 mg, 34%) in the form of a white solid.

Aufarbeitung

concentrationThereafter, the reaction solution was concentrated in vacuo
customthe obtained residue was then purified by silica gel column chromatography (chloroform:methanol=10:1)

Quellen und Nachweise

ORD-Eintrag: ord-986309b8482c457dabb3eccf3f790fae
Quelldatensatz: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08921576B2

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