3-Methyl-2-furoic acid → methyl 5-[4-({3-[(3-methyl-2-furoyl)amino]phenyl}amino)pyridin-2-yl]-1H-pyrrole-3-carboxylate

HRID 1915050

Reaktionsgleichung

Reaktionsgleichung von HRID 1915050
[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[NH2:43][C:44]1[CH:45]=[C:46]([NH:50][C:51]2[CH:56]=[CH:55][N:54]=[C:53]([C:57]3[NH:61][CH:60]=[C:59]([C:62]([O:64][CH3:65])=[O:63])[CH:58]=3)[CH:52]=2)[CH:47]=[CH:48][CH:49]=1>CN(C=O)C.O>[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([NH:43][C:44]1[CH:45]=[C:46]([NH:50][C:51]2[CH:56]=[CH:55][N:54]=[C:53]([C:57]3[NH:61][CH:60]=[C:59]([C:62]([O:64][CH3:65])=[O:63])[CH:58]=3)[CH:52]=2)[CH:47]=[CH:48][CH:49]=1)=[O:9]

Komponenten

7

Edukt 4

HCID 781273-Methyl-2-furoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67042564methyl 5-(4-((3-aminophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate

Produkt 1

HCID 58167905methyl 5-[4-({3-[(3-methyl-2-furoyl)amino]phenyl}amino)pyridin-2-yl]-1H-pyrrole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-methyl-2-furoic acid (22 mg, 0.18 mmol), HATU (73 mg, 0.19 mmol) and N,N-diisopropylethylamine (45 mg, 0.35 mmol) in anhydrous DMF (10 ml) was stirred at room temperature for 10 minutes, followed by addition of methyl 5-(4-((3-aminophenyl)amino)pyridin-2-yl)-1H-pyrrole-3-carboxylate (50 mg, 0.16 mmol). The mixture was stirred at room temperature for 3 hours and poured into 100 ml of water. The precipitates were filtered, washed with water and dried in vacuo to give methyl 5-[4-({3-[(3-methyl-2-furoyl)amino]phenyl}amino)pyridin-2-yl]-1H-pyrrole-3-carboxylate as off-white solid. Yield: 10 mg, 15%.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. filtrationThe precipitates were filtered
  3. washwashed with water
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-60620a1da99244e8934bf72220e59ce1
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08614234B2

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