3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(1-Amino-cyclobutyl)-phenyl]-5-fluoro-2-phenyl-chromen-4-one

HRID 1037161Notes

Reaction equation

HRID 1037161 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:56](=[O:57])[C:55]4[C:50](=[CH:51][CH:52]=[CH:53][C:54]=4[F:58])[O:49][C:48]=3[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C>>[NH2:36][C:37]1([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[CH:51][CH:52]=[CH:53][C:54]=4[F:58])[O:49][C:48]=3[C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)=[CH:45][CH:46]=2)[CH2:38][CH2:39][CH2:40]1

Participants

3

Reactant 2

HCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067716(1-[4-(5-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510306003-[4-(1-Amino-cyclobutyl)-phenyl]-5-fluoro-2-phenyl-chromen-4-oneYield 73.2%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(5-fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (19 mg, 0.039 mmol) was reacted to give the title compound (11 mg, 73%). LCMS (Method F): RT=8.60 min, [M+H]+=386. 1H NMR (400 MHz, CDCl3): δ 7.63-7.54 (m, 1H), 7.38-7.27 (m, 6H), 7.27-7.20 (m, 2H), 7.15 (d, J=8.6 Hz, 2H), 7.03 (t, J=8.6 Hz, 1H), 2.57-2.47 (m, 2H), 2.24-2.12 (m, 2H), 2.12-1.99 (m, 1H), 1.78-1.66 (m, 1H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-56d67697c3d9419888c2b571812db638
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…