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-carboxylic acid amide

HRID 1037180Notes

Reaction equation

HRID 1037180 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:61][CH3:62])=[C:53]([C:58](=[O:60])[NH2:59])[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]([O:61][CH3:62])=[C:53]([C:58]([NH2:59])=[O:60])[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 67067752{1-[4-(6-Carbamoyl-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butylester

Product 1

HCID 510306933-[4-(1-Amino-cyclobutyl)-phenyl]-7-methoxy-4-oxo-2-phenyl-4H-chromene-6-carboxylic acid amideYield 58.3%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(6-carbamoyl-7-methoxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butylester (40 mg, 0.074 mmol) was reacted to give the title compound (19 mg, 58%). LCMS (Method E): RT=3.15 min, [M+H]+=441. 1H NMR (400 MHz, DMSO-d6): δ 8.44 (s, 1H), 7.68 (d, J=7.7 Hz, 2H), 7.41-7.26 (m, 8H), 7.10 (d, J=8.3 Hz, 2H), 3.98 (s, 3H), 3.27 (s, 2H), 2.39-2.29 (m, 2H), 2.11-2.02 (m, 2H), 2.00-1.89 (m, 1H), 1.67-1.55 (m, 1H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-37d85d6860b547a9995815c690d7db4b
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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