4-Amino-1-Boc-piperidine → 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-methoxy-N-(piperidin-4-yl)benzamide

HRID 1880834

Reaktionsgleichung

Reaktionsgleichung von HRID 1880834
[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[O: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.[NH2:57][CH:58]1[CH2:63][CH2:62][N:61](C(OC(C)(C)C)=O)[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:57][CH:58]5[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]5)=[O:27])=[CH:24][C:23]=4[O:31][CH3:32])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 12682914-Amino-1-Boc-piperidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 252529054-(9-Cyclopentyl-7,7-difluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid

Produkt 1

HCID 252530654-(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-methoxy-N-(piperidin-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[5,4-b][1,4]diazepin-2-ylamino)-3-methoxybenzoic acid as described in the General procedure for amide bond synthesis using HATU and tert-butyl 4-aminopiperidine-1-carboxylate, where Boc was removed using TFA in DCM. The final compound was purified by reverse phase HPLC and basified to give the free base. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43 (qd, J=11.9, 3.8 Hz, 2 H) 1.54-1.66 (m, 5 H) 1.66-1.77 (m, 4 H) 1.98 (br. s, 2 H) 2.52 (d, J=1.8 Hz, 2 H) 2.98 (d, J=11.9 Hz, 2 H) 3.79-3.87 (m, 1 H) 3.93 (s, 3 H) 4.04 (t, J=14.2 Hz, 2 H) 4.76 (quin, J=8.1 Hz, 1 H) 7.48 (d, 1 H) 7.50 (s, 1 H) 7.96 (s, 1 H) 8.13 (d, J=8.1 Hz, 1 H) 8.26 (d, J=8.1 Hz, 1 H) 8.26 (s, 1 H). [M+H] calc'd for C26H33F2N7O3, 530; found 530.

Aufarbeitung

  1. customas described in the General procedure for amide bond synthesis
  2. customwas removed
  3. customThe final compound was purified by reverse phase HPLC
  4. customto give the free base

Quellen und Nachweise

ORD-Eintrag
ord-301774540e3f435b9c37042882b9a89b
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318727B2

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