3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(1-Amino-cyclobutyl)-phenyl]-7-chloro-2-phenyl-pyrano[2,3-b]pyridin-4-one hydrochloride
Reaction equation
NC1(C2C=CC(C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=CC=2)CCC1.C(OC(=O)[NH:36][C:37]1([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:48](=[O:64])[C:49]4[C:50]([O:56][C:57]=3[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[N:51][C:52]([Cl:55])=[CH:53][CH:54]=4)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C>>[ClH:55].[NH2:36][C:37]1([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[C:48](=[O:64])[C:49]4[C:50]([O:56][C:57]=3[C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)=[N:51][C:52]([Cl:55])=[CH:53][CH:54]=4)=[CH:45][CH:46]=2)[CH2:40][CH2:39][CH2:38]1Participants
Reactant 2
Product 1
Procedure
Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(7-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-b]pyridin-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as the free base. The residue was dissolved in a mixture of MeOH (1 mL), water (4 mL) and 1 M HCl (0.15 mL) and chromatographed on a 2 g C18 cartridge {gradient 30 to 90% MeOH in water+1 M HCl (60 μL in each 5 mL of eluent)} to give the title compound (3.7 mg, 50%) as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.61 (d, J=8.3 Hz, 1H), 7.67 (d, J=8.0 Hz, 1H), 7.49-7.47 (m, 4H), 7.43-7.30 (m, 5H), 2.81-2.74 (m, 2H), 2.63-2.56 (m, 2H), 2.29-2.19 (m, 1H), 2.02-1.91 (m, 1H). LCMS (Method F): RT=8.90 min, [M+Na]+=418/420.
Workup
- customwas reacted
Sources & evidence
- ORD record
- ord-3b1db51166e245eb978b478349d9ab7e
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546376B2
Reaction notes
Loading…