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-ethyl-N-(1-methylpiperidin-4-yl)benzamide

HRID 1880851

Reaktionsgleichung

Reaktionsgleichung von HRID 1880851
[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]([OH:28])=O)=[CH:24][C:23]=4[CH2:31][CH3:32])=[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.[CH3:57][N:58]1[CH2:63][CH2:62][CH:61]([NH2:64])[CH2:60][CH2:59]1>>[CH:1]1([N:6]2[CH2:12][C:11]([F:13])([F:14])[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:64][CH:61]5[CH2:62][CH2:63][N:58]([CH3:57])[CH2:59][CH2:60]5)=[O:28])=[CH:24][C:23]=4[CH2:31][CH3:32])=[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 580150654-(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-ethylbenzoic acid

Produkt 1

HCID 252535294-(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-ethyl-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-ethylbenzoic 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 1.14 (t, J=8.0 Hz, 3 H) 1.23-1.69 (m, 11 H) 1.77 (m, 4 H) 1.99 (m, 2 H) 2.20 (s, 3 H) 2.69 (q, J=7.3 Hz, 2 H) 3.75 (s, 1 H) 3.97 (t, J=14.2 Hz, 2 H) 4.54 (t, J=8.1 Hz, 1 H) 7.57-7.81 (m, 3 H) 8.12 (d, J=7.8 Hz, 1 H) 8.17 (s, 1 H) 8.61 (s, 1 H). [M+H] calc'd for C28H37F2N7O2, 542; found 542.

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 1.14 (t, J=8.0 Hz, 3 H) 1.23-1.69 (m, 11 H) 1.77 (m, 4 H) 1.99 (m, 2 H) 2.20 (s, 3 H) 2.69 (q, J=7.3 Hz, 2 H) 3.75 (s, 1 H) 3.97 (t, J=14.2 Hz, 2 H) 4.54 (t, J=8.1 Hz, 1 H) 7.57-7.81 (m, 3 H) 8.12 (d, J=7.8 Hz, 1 H) 8.17 (s, 1 H) 8.61 (s, 1 H)

Quellen und Nachweise

ORD-Eintrag
ord-537c68a3785b4574914aa6815b6cca84
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318727B2

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