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Diisopropylethylamine → 3-methoxy-4-[[5-methyl-6-oxidanylidene-9-(phenylmethyl)-7,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl]amino]-N-(1-methylpiperidin-4-yl)benzamide

HRID 2111313
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2111313
[CH2:1]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH3:16])[C:10]2[CH:17]=[N:18][C:19]([NH:21][C:22]3[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=3[O:31][CH3:32])=[N:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.C(N(C(C)C)C(C)C)C.[NH2:66][CH:67]1[CH2:72][CH2:71][N:70]([CH3:73])[CH2:69][CH2:68]1>O.C(=O)(O)[O-].[Na+].CN(C)C=O>[CH2:1]([N:8]1[CH2:14][CH2:13][C:12](=[O:15])[N:11]([CH3:16])[C:10]2[CH:17]=[N:18][C:19]([NH:21][C:22]3[CH:30]=[CH:29][C:25]([C:26]([NH:66][CH:67]4[CH2:72][CH2:71][N:70]([CH3:73])[CH2:69][CH2:68]4)=[O:27])=[CH:24][C:23]=3[O:31][CH3:32])=[N:20][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
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Komponenten

8

Edukt 4

HCID 81531DiisopropylethylamineHCID 27375314-Amino-1-methylpiperidineHCID 581539094-(9-benzyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl amino)-3-methoxy-benzoic acidHCID 178484293HCID 178484293, Verbindung

Produkt 1

HCID 42610360
3-methoxy-4-[[5-methyl-6-oxidanylidene-9-(phenylmethyl)-7,8-dihydropyrimido[4,5-b][1,4]diazepin-2-yl]amino]-N-(1-methylpiperidin-4-yl)benzamide
Ausbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of 0.056 g (0.00013 mole) of 4-(9-benzyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-yl amino)-3-methoxy-benzoic acid, 0.054 g (0.00014 mole) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide hexafluorophosphate, 0.079 mL (0.00046 mole) of ethyldiisopropyl amine and 2.0 mL of dimethylformamide was stirred for 5 minutes and then 0.022 g (0.0002 mole) of 4-amino-1-methyl-piperidine was added. The mixture was stirred for 3 hours, then diluted with 10 mL of water plus 2 mL of saturated sodium bicarbonate and then extracted 3 times with 10 mL of ethyl acetate. The combined extracts were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by C18 reverse phase silica gel chromatography, eluting with an acetonitrile-water gradient (20:80-100:0) to give 0.045 g of 4-(9-benzyl-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide (I-22) as a white solid.

Aufarbeitung

  1. stirringThe mixture was stirred for 3 hours
  2. extractionextracted 3 times with 10 mL of ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by C18 reverse phase silica gel chromatography
  8. washeluting with an acetonitrile-water gradient (20:80-100:0)

Quellen und Nachweise

ORD-Eintrag
ord-53e260a5206746439130a2cfe85be764
Quelldatensatz
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07517873B2

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