Diisopropylethylamine → 3,5-dichloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-2-fluoro-N-(1-methyl-4-piperidyl)benzamide

HRID 2234312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234312
[Cl:1][C:2]1[C:3]([F:31])=[C:4]([CH:8]=[C:9]([Cl:30])[C:10]=1[NH:11][C:12]1[N:22]=[C:21]2[C:15]([N:16]([CH3:29])[C:17](=[O:28])[CH2:18][CH2:19][N:20]2[CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:14][N:13]=1)[C:5](O)=[O:6].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:56][CH:57]1[CH2:62][CH2:61][N:60]([CH3:63])[CH2:59][CH2:58]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:1][C:2]1[C:3]([F:31])=[C:4]([CH:8]=[C:9]([Cl:30])[C:10]=1[NH:11][C:12]1[N:22]=[C:21]2[C:15]([N:16]([CH3:29])[C:17](=[O:28])[CH2:18][CH2:19][N:20]2[CH:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:14][N:13]=1)[C:5]([NH:56][CH:57]1[CH2:62][CH2:61][N:60]([CH3:63])[CH2:59][CH2:58]1)=[O:6]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866175623,5-Dichloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-2-fluoro-benzoic acid2×

Produkt 1

HCID 866175613,5-dichloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-2-fluoro-N-(1-methyl-4-piperidyl)benzamideAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3,5-dichloro-4-[(2-cyclopentyl-6-methyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-2-fluoro-benzoic acid (Intermediate 221; 85 mg, 0.18 mmol), HATU (104 mg, 0.27 mmol) and 4-amino-1-methylpiperidine (32 mg, 0.27 mmol) were stirred in DMF (3 mL) and diisopropylethylamine (95 μl, 0.54 mmol) added. The mixture was stirred for 2 hours and absorbed on to an SCX column, which was subsequently washed with methanol and eluted with ammonia in methanol. Product containing fractions were combined and evaporated and the residue purified by column chromatography (4% ammonia in methanol/DCM) to yield the title compound as a white solid (67 mg, 66%).

Aufarbeitung

  1. customabsorbed on to an SCX column, which
  2. washwas subsequently washed with methanol
  3. washeluted with ammonia in methanol
  4. additionProduct containing fractions
  5. customevaporated
  6. customthe residue purified by column chromatography (4% ammonia in methanol/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-27fcd5d0ea5841b9847fde6b9d12cb75
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709471B2

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