3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 7-[4-(1-Amino-cyclobutyl)-phenyl]-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-one

HRID 1037291Notes

Reaction equation

HRID 1037291 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:48](=[O:72])[C:49]4[C:54]([O:55][C:56]=3[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[C:53]3[N:63](S(=O)(=O)N(C)C)[N:64]=[CH:65][C:52]3=[CH:51][CH:50]=4)=[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:48](=[O:72])[C:49]4[C:54]([O:55][C:56]=3[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[C:53]3[NH:63][N:64]=[CH:65][C:52]3=[CH:51][CH:50]=4)=[CH:45][CH:46]=2)[CH2:40][CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067771{1-[4-(1-Dimethylsulfamoyl-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510299497-[4-(1-Amino-cyclobutyl)-phenyl]-8-phenyl-1H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-oneYield 71%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(1-dimethylsulfamoyl-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a white solid (31 mg, 71%). 1H NMR (400 MHz, DMSO-d6): δ 14.26 (bs, 1H), 8.32 (s, 1H), 7.77 (d, J=8.5 Hz, 1H), 7.68 (d, J=8.5 Hz, 1H), 7.53-7.49 (m, 2H), 7.41-7.30 (m, 5H), 7.14 (d, J=8.5 Hz, 2H), 3.28 (bs, 2H), 2.40-2.32 (m, 2H), 2.12-2.03 (m, 2H), 2.02-1.91 (m, 1H), 1.68-1.57 (m, 1H). LCMS (Method E): RT=3.05 min, [M+H]+=408.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-58938bed95ea45698fdf979daf01bbfb
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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