Reaktion #2134697

ord-e1498c660c5245f197fd0955aa34de71

Reaktionsgleichung

C[C@@H]1CCCN1[C@H]1C[C@H](c2nc3ccc(Br)cc3s2)C1
product
C[C@@H]1CCCN1[C@H]1C[C@H](c2nc3ccc(Br)cc3s2)C1
Trans-6-bromo-2-{3-[(2R)-2-methylpyrrolidin-1-yl]cyclobutyl}-1,3-benzothiazole
CC1(C)OB(c2cnc3ccccc3c2)OC1(C)C
3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline
OB(O)c1cncnc1
pyrimidine-5-boronic acid
C[C@H]1CCCN1[C@H]1C[C@H](c2nc3ccc(-c4cnc5ccccc5c4)cc3s2)C1
title compound
C[C@H]1CCCN1[C@H]1C[C@H](c2nc3ccc(-c4cnc5ccccc5c4)cc3s2)C1
Trans-3-(2-{3-[(2S)-2-methylpyrrolidin-1-yl]cyclobutyl}-1,3-benzothiazol-6-yl)quinoline

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The title compound was prepared according to the procedure described in Example 1F, substituting the product of Example 11A for the product of Example 1E and substituting 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-quinoline for pyrimidine-5-boronic acid. 1H NMR (500 MHz, CDCl3) δ ppm 9.24 (d, J=2.50 Hz, 1H) 8.37 (d, J=2.50 Hz, 1H) 8.09-8.21 (m, 3H) 7.90 (d, J=8.11 Hz, 1H) 7.81 (dd, J=8.42, 1.87 Hz, 1H) 7.71-7.78 (m, 1H) 7.54-7.66 (m, 1H) 3.82-3.99 (m, 1H) 3.46-3.64 (m, 1H) 2.98-3.16 (m, 1H) 2.65-2.86 (m, 2H) 2.42-2.64 (m, 2H) 2.28-2.41 (m, 1H) 1.92-2.05 (m, 1H) 1.81-1.89 (m, 1H) 1.69-1.78 (m, 1H) 1.44-1.63 (m, 2H) 1.16 (s, 3H). MS: (M+H)+=400.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08592467B2uspto-grants-2013_11