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-carboxylic acid amide

HRID 1037226Notes

Reaction equation

HRID 1037226 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](=[O:62])[NH2:61])=[C:53]([O:58][CH3:59])[CH:54]=4)[O:49][C:48]=3[C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=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]([NH2:61])=[O:62])=[C:53]([O:58][CH3:59])[CH:54]=4)[O:49][C:48]=3[C:63]3[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=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 67067954(1-[4-(7-Carbamoyl-6-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510309763-[4-(1-Amino-cyclobutyl)-phenyl]-6-methoxy-4-oxo-2-phenyl-4H-chromene-7-carboxylic acid amideYield 93%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(7-carbamoyl-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 (17 mg, 93%). 1H NMR (400 MHz, DMSO-d6): δ 7.99 (s, 1H), 7.91-7.88 (br s, 1H), 7.85-7.81 (br s, 1H), 7.59 (s, 1H), 7.45-7.31 (m, 7H), 7.16-7.11 (m, 2H), 3.98 (s, 3H), 2.41-2.33 (m, 2H), 2.13-2.04 (m, 2H), 2.04-1.94 (m, 1H), 1.70-1.60 (m, 1H). LCMS (Method E): RT=2.99 min, [M+H]+=441.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-de284cb6465f439693dc49ac7d33f520
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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