3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(1-Amino-cyclobutyl)-phenyl]-7-methoxy-4-oxo-2-phenyl-4H-chromene-8-carbonitrile

HRID 1037184Notes

Reaction equation

HRID 1037184 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:60]#[N:61])[C:52]([O:58][CH3:59])=[CH:53][CH:54]=4)[O:49][C:48]=3[C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=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]([C:60]#[N:61])[C:52]([O:58][CH3:59])=[CH:53][CH:54]=4)[O:49][C:48]=3[C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=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 67067666(1-[4-(8-Cyano-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510306953-[4-(1-Amino-cyclobutyl)-phenyl]-7-methoxy-4-oxo-2-phenyl-4H-chromene-8-carbonitrileYield 43%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(8-cyano-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (15 mg, 0.0287 mmol) was reacted to give the title compound (5.2 mg, 43%). LCMS (Method E): RT=3.47 min, M+H+=423. 1H NMR (400 MHz, CDCl3): δ 8.43 (d, J=9.3 Hz, 1H), 7.49-7.44 (m, 2H), 7.41-7.33 (m, 3H), 7.29 (d, J=7.4 Hz, 2H), 7.20 (d, J=7.4 Hz, 2H), 7.08 (d, J=9.0 Hz, 2H), 4.11 (s, 3H), 2.61-2.51 (m, 2H), 2.23-2.02 (m, 3H), 1.83-1.64 (m, 1H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-179bf9e9fa7a4e26aacfbe9c6f6fbb52
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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