Ro3280 → 4-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide

HRID 914139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 914139
[CH:1]1([N:6]2[CH2:12][C:11](F)([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:37]=[CH:36][C:25]([C:26]([NH:28][CH:29]5[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]5)=[O:27])=[CH:24][C:23]=4[O:38][CH3:39])=[N:20][C:7]2=3)[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(C([O-])=O)CN>>[CH:1]1([N:6]2[CH2:12][CH:11]([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:37]=[CH:36][C:25]([C:26]([NH:28][CH:29]5[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]5)=[O:27])=[CH:24][C:23]=4[O:38][CH3:39])=[N:20][C:7]2=3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

3

Edukt 2

HCID 25015677Ro3280HCID 866358932-Fluoro-beta-alaninate

Produkt 1

HCID 252551064-(9-cyclopentyl-7-fluoro-5-methyl-6-oxo-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,4]diazepin-2-ylamino)-3-methoxy-N-(1-methylpiperidin-4-yl)benzamide

Versuchsvorschrift

The title compound was synthesized using an analogous procedure to that described in connection with Compound 3 except that 2-fluoro-beta-alaninate was used as the starting material. The final product was purified on reversed phase HPLC as TFA salt. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.55-1.87 (m, 11H) 1.91-2.08 (m, 3H) 2.18 (s, 3H) 2.79 (d, J=11.4 Hz, 2H) 3.24 (s, 3H) 3.61-3.83 (m, 3H) 3.94 (s, 3H) 4.77 (quin., J=8.3 Hz, 1H) 5.52 (qd, 1H) 7.47 (dd, J=1.8 Hz, 1H) 7.49 (s, 1H) 7.86 (s, 1H) 8.11 (d, J=7.8 Hz, 1H) 8.16 (s, 1H) 8.33 (d, J=8.34 Hz, 1H). [M+H] calc'd for C27H36FN7O3 526. found 526.

Aufarbeitung

  1. customThe final product was purified on reversed phase HPLC as TFA salt

Quellen und Nachweise

ORD-Eintrag
ord-4270a0ff8c7744eba0a53641e6392fc5
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08026234B2

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