3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 4-{3-[4-(1-Amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromen-8-yl}-piperazin-2-one

HRID 1037343Notes

Reaction equation

HRID 1037343 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](=[C:51]([N:58]5[CH2:63][CH2:62][NH:61][C:60](=[O:64])[CH2:59]5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=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](=[C:51]([N:58]5[CH2:63][CH2:62][NH:61][C:60](=[O:64])[CH2:59]5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)=[CH:45][CH:46]=2)[CH2:40][CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067777(1-{4-[4-oxo-8-(3-oxo-piperazin-1-yl)-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510302324-{3-[4-(1-Amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromen-8-yl}-piperazin-2-oneYield 28%

Procedure

Following the procedure of 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{-4-[4-oxo-8-(3-oxo-piperazin-1-yl)-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester was reacted to give the title compound as a white solid (8 mg, 28%). 1H NMR (400 MHz, CDCl3): δ 7.92 (s, 1H), 7.69 (dd, J=7.4, 1.7 Hz, 1H), 7.41-7.26 (m, 9H), 7.09 (d, J=8.0 Hz, 2H), 3.71 (s, 2H), 3.40 (t, J=5.4 Hz, 2H), 3.35-2.99 (m, 4H), 2.36-2.27 (m, 2H), 2.07-1.87 (m, 3H), 1.65-1.53 (m, 1H). LCMS (Method E): RT=2.79 min, [M+H]+=466.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-f598ad60a52f41678b0ed68097efb8a2
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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