Triethylamine → 1-Methyl-1H-pyrrole-2-carboxylic acid N'-(1-{2-[3-((E)-2-pyridin-2-yl-vinyl)-1H-indazol4-ylamino]-phenyl}-methanoyl)-hydrazide

HRID 1827471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1827471
N1C=CC=CC=1[CH:7]=[CH:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([NH:18][C:19]3[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=3[C:21]([OH:23])=O)=[CH:15][CH:16]=2)[NH:11][N:10]=1.[CH3:28][N:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([NH:36][NH2:37])=[O:35].C(N(CC)CC)C.CN(C(ON1N=N[C:55]2[CH:56]=[CH:57][CH:58]=[N:59][C:54]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[N:59]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1/[CH:7]=[CH:8]/[C:9]1[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][C:14]=2[NH:18][C:19]2[CH:27]=[CH:26][CH:25]=[CH:24][C:20]=2[C:21]([NH:37][NH:36][C:34]([C:30]2[N:29]([CH3:28])[CH:33]=[CH:32][CH:31]=2)=[O:35])=[O:23])[NH:11][N:10]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 27636101-methyl-1H-pyrrole-2-carbohydrazideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 693529632-[3-(2-Pyridin-2-yl-vinyl)-1H-indazol-6-ylamino]-benzoic acid

Produkt 1

HCID 696528951-Methyl-1H-pyrrole-2-carboxylic acid N'-(1-{2-[3-((E)-2-pyridin-2-yl-vinyl)-1H-indazol4-ylamino]-phenyl}-methanoyl)-hydrazideAusbeute 40,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-[3-(2-Pyridin-2-yl-vinyl)-1H-indazol-6-ylamino]-benzoic acid (50.0 mg, 0.084 mmol), 1-methyl-1H-pyrrole-2-carboxylic acid hydrazide (23.3 mg, 0.17 mmol), triethylamine(58 μl, 0.42 mmol), dissolved in DMF (0.8 mL), was treated with HATU (48 mg, 0.13 mmol). The mixture was stirred overnight, then purified by reverse phase HPLC yielding 16.1 mg (40%) of the title compound as a yellow solid. 1H NMR (DMSO-d6): δ 10.39 (1H, s), 10.00 (1H, s), 9.52 (1H, s), 8.67 (1H, d, J=2.4), 8.07 (4H, m), 7.77 (1H, d, J=5.2), 7.51 (4H, m), 7.32 (1H, s), 7.09 (1H, d, J=6.3), 6.98 (3H, m), 6.13 (1H, m), 3.87 (3H, s). ESIMS (M+H+):478.1.

Aufarbeitung

  1. custompurified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-12d9c302ed5c412ab8d0e528d1720e00
Quelldatensatz
uspto-grants-2006_05
Patentnummer
US07053107B2

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