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

HRID 2234303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2234303
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14]1[N:24]=[C:23]2[C:17]([N:18]([CH3:29])[C:19](=[O:28])[CH2:20][CH2:21][N:22]2[CH:25]([CH3:27])[CH3:26])=[CH:16][N:15]=1)[C:7](O)=[O:8])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:54][CH:55]1[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14]1[N:24]=[C:23]2[C:17]([N:18]([CH3:29])[C:19](=[O:28])[CH2:20][CH2:21][N:22]2[CH:25]([CH3:26])[CH3:27])=[CH:16][N:15]=1)[C:7]([NH:54][CH:55]1[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]1)=[O:8])[CH3:2]

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 686853493-Ethoxy-4-[(6-methyl-5-oxo-2-propan-2-yl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]benzoic acid2×

Produkt 1

HCID 686838133-ethoxy-4-[(6-methyl-5-oxo-2-propan-2-yl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-N-(1-methyl-4-piperidyl)benzamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-ethoxy-4-[(6-methyl-5-oxo-2-propan-2-yl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]benzoic acid (Intermediate 163; 80 mg, 0.20 mmol), HATU (115 mg, 0.30 mmol) and 4-amino-1-methylpiperidine (Fluorochem; 35 mg, 0.30 mmol) in DMF (5 mL) was added diisopropylethylamine (105 μl, 0.60 mmol). The mixture was stirred for 2 hours at room temperature and then absorbed on to an SCX column, washed with methanol and eluted with ammonia in methanol. Product containing fractions were concentrated and purified by column chromatography (5% ammonia in methanol/DCM) to yield the title compound as a white foam (87 mg, 88%).

Aufarbeitung

  1. customabsorbed on to an SCX column
  2. washwashed with methanol
  3. washeluted with ammonia in methanol
  4. additionProduct containing fractions
  5. concentrationwere concentrated
  6. custompurified by column chromatography (5% ammonia in methanol/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-92f0bf975dd14e2f98ed911f071872ae
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07709471B2

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