4-Amino-1-methylpiperidine → 4-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-fluoro-N-(1-methylpiperidin-4-yl)benzamide

HRID 1880847

Reaktionsgleichung

Reaktionsgleichung von HRID 1880847
[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][C:23]=4[F:31])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:56][N:57]1[CH2:62][CH2:61][CH:60]([NH2:63])[CH2:59][CH2:58]1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:14])([F:13])[C:10](=[O:15])[N:9]([CH3:16])[C:8]3[CH:17]=[N:18][C:19]([NH:21][C:22]4[CH:30]=[CH:29][C:25]([C:26]([NH:63][CH:60]5[CH2:61][CH2:62][N:57]([CH3:56])[CH2:58][CH2:59]5)=[O:27])=[CH:24][C:23]=4[F:31])=[N:20][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

4

Edukt 3

HCID 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 580150834-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-fluoro-benzoic acid

Produkt 1

HCID 252533734-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-fluoro-N-(1-methylpiperidin-4-yl)benzamide

Versuchsvorschrift

The title compound was synthesized from 4-(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-fluorobenzoic acid as described in the General procedure for amide bond synthesis using HATU and 1-methylpiperidin-4-amine. The final compound was purified by reverse phase HPLC and basified to give the free base 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50-1.75 (m, 12 H) 1.99 (m, 3 H) 2.19 (s, 3 H) 2.79 (m, 2 H) 3.74 (m, 1 H) 4.01 (t, J=14.0 Hz, 2 H) 4.68 (m, 1 H) 7.67 (d, J=8.6 Hz, 1 H) 7.72 (d, J=12.4 Hz, 1 H) 7.99 (t, J=8.2 Hz, 1 H) 8.20 (d, J=7.3 Hz, 1 H) 8.23 (s, 1 H) 9.08 (s, 1 H). [M+H] calc'd for C26H32F3N7O2, 532; found 532.

Aufarbeitung

  1. customas described in the General procedure for amide bond synthesis
  2. customThe final compound was purified by reverse phase HPLC
  3. customto give the free base 1H NMR (400 MHz, DMSO-d6) δ ppm 1.50-1.75 (m, 12 H) 1.99 (m, 3 H) 2.19 (s, 3 H) 2.79 (m, 2 H) 3.74 (m, 1 H) 4.01 (t, J=14.0 Hz, 2 H) 4.68 (m, 1 H) 7.67 (d, J=8.6 Hz, 1 H) 7.72 (d, J=12.4 Hz, 1 H) 7.99 (t, J=8.2 Hz, 1 H) 8.20 (d, J=7.3 Hz, 1 H) 8.23 (s, 1 H) 9.08 (s, 1 H)

Quellen und Nachweise

ORD-Eintrag
ord-de01ea094bf44b0cb179a61bd02391c4
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318727B2

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