3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → HCID 178507111, compound

HRID 1037341Notes

Reaction equation

HRID 1037341 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]([C:58]5[C:59]([C:63]([F:66])([F:65])[F:64])=[N:60][NH:61][CH:62]=5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=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:46]=[CH:45][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[C:51]([C:58]5[C:59]([C:63]([F:66])([F:65])[F:64])=[N:60][NH:61][CH:62]=5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:67]3[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=3)=[CH:43][CH:42]=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 178452579HCID 178452579, compound

Product 1

HCID 178507111HCID 178507111, compoundYield 28%

Procedure

Following the procedure of 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{4-[4-oxo-2-phenyl-8-(3-trifluoromethyl-1H-pyrazol-4-yl)-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 8.31 (s, 1H), 8.11 (dd, J=8.1 and 1.8 Hz, 1H), 7.74 (dd, J=7.4 and 1.6 Hz, 1H), 7.54 (t, J=7.9 Hz, 1H), 7.36-7.27 (m, 3H), 7.26-7.18 (m, 4H), 7.08 (d, J=8.4 Hz, 2H), 3.27 (bs, 3H), 2.36-2.26 (m, 2H), 2.08-1.87 (m, 3H), 1.65-1.53 (m, 1H). LCMS (Method E): RT=3.41 min, [M+H]+=502.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-98c5ce9e58274912b03a039c0bf4c1e8
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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