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-6-carbonitrile

HRID 1037182Notes

Reaction equation

HRID 1037182 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][C:52]([O:60][CH3:61])=[C:53]([C:58]#[N:59])[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](=[CH:51][C:52]([O:60][CH3:61])=[C:53]([C:58]#[N:59])[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 67067795{1-[4-(6-Cyano-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510306943-[4-(1-Amino-cyclobutyl)-phenyl]-7-methoxy-4-oxo-2-phenyl-4H-chromene-6-carbonitrileYield 60%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(6-cyano-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (81 mg, 0.155 mmol) was reacted to give the title compound (39 mg, 60%). LCMS (Method E): RT=3.57 min, [M+H]+=423. 1H NMR (400 MHz, DMSO-d6): δ 8.36 (s, 1H), 7.53 (s, 1H), 7.41-7.26 (m, 7H), 7.09 (d, J=8.1 Hz, 2H), 4.01 (s, 3H), 2.85 (bs, 2H), 2.37-2.27 (m, 2H), 2.10-1.88 (m, 3H), 1.66-1.54 (m, 1H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-b52477a02398422ea8fcc973898a7e15
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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