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

HRID 1037228Notes

Reaction equation

HRID 1037228 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]([C:60]#[N:61])=[C:53]([O:58][CH3:59])[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]([C:60]#[N:61])=[C:53]([O:58][CH3:59])[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 67067736(1-[4-(7-Cyano-6-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510295883-[4-(1-Amino-cyclobutyl)-phenyl]-6-methoxy-4-oxo-2-phenyl-4H-chromene-7-carbonitrileYield 71%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(7-cyano-6-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a pale yellow solid (23 mg, 71%). 1H NMR (400 MHz, DMSO-d6): δ 8.41 (s, 1H), 7.65 (s, 1H), 7.43-7.32 (m, 7H), 7.16-7.12 (m, 2H), 4.02 (s, 3H), 2.42-2.35 (m, 2H), 2.17-2.09 (m, 2H), 2.06-1.96 (m, 1H), 1.72-1.62 (m, 1H). LCMS (Method E): RT=3.67 min, [M+H]+=423.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-03763a75951343ce9754d2d448901e7a
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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