4-Amino-1-methylpiperidine → 3-Chloro-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)-N-(1-methylpiperidin-4-yl)benzamide

HRID 914078

Reaktionsgleichung

Reaktionsgleichung von HRID 914078
[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[Cl: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>>[Cl:31][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:22]=1[NH:21][C:19]1[N:18]=[CH:17][C:8]2[N:9]([CH3:16])[C:10](=[O:15])[C:11]([F:13])([F:14])[CH2:12][N:6]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)[C:7]=2[N:20]=1)[C:26]([NH:63][CH:60]1[CH2:61][CH2:62][N:57]([CH3:56])[CH2:58][CH2:59]1)=[O:28]

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 671178444-(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-chlorobenzoic acid

Produkt 1

HCID 252535263-Chloro-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)-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-chlorobenzoic 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 1.44-1.77 (m, 15H) 2.23 (s, 3H) 2.84 (m, 2H) 3.96-4.07 (t, J=12 Hz, 2H) 4.66 (m, 1H) 7.80 (dd, J=8.5, 1.9 Hz, 1H) 8.00 (d, J=1.8 Hz, 1H) 8.08 (d, J=8.6 Hz, 1H) 8.19-8.33 (m, 2H) 8.58 (s, 1H). [M+H] calc'd for C26H32ClF2N7O2, 548. found 548.

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 1.44-1.77 (m, 15H) 2.23 (s, 3H) 2.84 (m, 2H) 3.96-4.07 (t, J=12 Hz, 2H) 4.66 (m, 1H) 7.80 (dd, J=8.5, 1.9 Hz, 1H) 8.00 (d, J=1.8 Hz, 1H) 8.08 (d, J=8.6 Hz, 1H) 8.19-8.33 (m, 2H) 8.58 (s, 1H)

Quellen und Nachweise

ORD-Eintrag
ord-4353c63fc31c4d5b9d1d134395e5c846
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026234B2

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