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

HRID 1037204Notes

Reaction equation

HRID 1037204 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]=[C:53]([N:58]5[CH2:63][CH2:62][N:61]([CH3:64])[CH2:60][CH2:59]5)[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](=[CH:51][CH:52]=[C:53]([N:58]5[CH2:63][CH2:62][N:61]([CH3:64])[CH2:60][CH2:59]5)[CH:54]=4)[O:49][C:48]=3[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=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 67067974(1-{4-[6-(4-methyl-piperazin-1-yl)-4-oxo-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510308803-[4-(1-Amino-cyclobutyl)-phenyl]-6-(4-methyl-piperazin-1-yl)-2-phenyl-chromen-4-oneYield 96%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{4-[6-(4-methyl-piperazin-1-yl)-4-oxo-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester was reacted to give the title compound as a yellow solid (12 mg, 96%). 1H NMR (400 MHz, DMSO-d6): as 7.63-7.56 (m, 2H), 7.41-7.29 (m, 8H), 7.13-7.09 (m, 2H), 3.25-3.20 (m, 4H), 2.52-2.47 (m, 4H), 2.41-2.32 (m, 2H), 2.24 (s, 3H), 2.12-2.04 (m, 2H), 2.04-1.94 (m, 1H), 1.69-1.60 (m, 1H). LCMS (Method F): RT=6.39 min, [M+H]+=466.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-79d460d24cb748aa80ff57c5e875fd17
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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