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

HRID 1037206Notes

Reaction equation

HRID 1037206 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]([C:58]#[N:59])[CH:54]=4)[O:49][C:48]=3[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=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]([C:58]#[N:59])[CH:54]=4)[O:49][C:48]=3[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=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 67067657{1-[4-(6-cyano-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510308813-[4-(1-Amino-cyclobutyl)-phenyl]-4-oxo-2-phenyl-4H-chromene-6-carbonitrileYield 94%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(6-cyano-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 (33 mg, 94%). 1H NMR (400 MHz, DMSO-d6): δ 8.51 (d, J=2 Hz, 1H), 8.27 (dd, J=2 and 8 Hz, 1H), 7.95 (d, J=8 Hz, 1H), 7.46-7.33 (m, 7H), 7.18-7.14 (m, 2H), 2.44-2.36 (m, 2H), 2.20-2.12 (m, 2H), 2.07-1.97 (m, 1H), 1.73-1.63 (m, 1H). LCMS (Method F): RT=8.47 min, [M+H]+=393.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-bb487acd08fd40ffb1097b8ac241dac4
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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