Diisopropylethylamine → 4-({7-[(3-fluoro-4-methoxybenzoyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl}oxy)-N-methylpyridine-2-carboxamide

HRID 1640223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1640223
[NH2:1][CH:2]1[CH2:11][C:10]2[CH:9]=[C:8]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:27](O)=[O:28].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CC(N(C)C)=O.CC(N(C)C)=O.CN1C(=O)CCC1.O>[F:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:27]([NH:1][CH:2]1[CH2:11][C:10]2[CH:9]=[C:8]([O:12][C:13]3[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH:21][CH3:22])=[O:20])[CH:14]=3)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1)=[O:28]

Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27334013-Fluoro-4-methoxybenzoic acidHCID 589024394-[(7-amino-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]-N-methylpyridine-2-carboxamide

Produkt 1

HCID 589024604-({7-[(3-fluoro-4-methoxybenzoyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl}oxy)-N-methylpyridine-2-carboxamideAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittelHCID 22717425N,N-dimethylacetamide 1-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-[(7-amino-5,6,7,8-tetrahydronaphthalen-2-yl)oxy]-N-methylpyridine-2-carboxamide (25 mg) in DMA (1 mL) were added 3-fluoro-4-methoxybenzoic acid (16 mg, 0.094 mmol), DIPEA (26 μL), and a solution of TBTU (41 mg, 0.128 mmol) in DMA:NMP (1:1 v/v, 1 mL). The reaction mixture was allowed to stir at rt for 24 h. Water was added and the mixture was extracted with DCM. The organic solution was concentrated and purified by reverse phase HPLC to give 4-({7-[(3-fluoro-4-methoxybenzoyl)amino]-5,6,7,8-tetrahydronaphthalen-2-yl}oxy)-N-methylpyridine-2-carboxamide (26.5 mg, 70%). LCMS: (AA) ES+450.5.

Aufarbeitung

  1. extractionthe mixture was extracted with DCM
  2. concentrationThe organic solution was concentrated
  3. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-bd9c7fa1a4ca48d8972d5e2531e847b6
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110687B2

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