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

HRID 1037298Notes

Reaction equation

HRID 1037298 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:67])[C:49]4[CH:50]=[CH:51][C:52]5[C:53](=[N:63][N:64]([CH3:66])[CH:65]=5)[C:54]=4[O:55][C:56]=3[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=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:48](=[O:67])[C:49]4[CH:50]=[CH:51][C:52]5[C:53](=[N:63][N:64]([CH3:66])[CH:65]=5)[C:54]=4[O:55][C:56]=3[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[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 68227371(1-[4-(2-Methyl-6-oxo-8-phenyl-2,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510299517-[4-(1-Amino-cyclobutyl)-phenyl]-2-methyl-8-phenyl-2H-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-6-oneYield 83%

Procedure

Following the procedure of 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(2-methyl-6-oxo-8-phenyl-2,6-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 (16 mg, 83%). 1H NMR (400 MHz, DMSO-d6): δ 8.55 (s, 1H), 7.69 (d, J=8.7 Hz, 1H), 7.58 (d, J=8.7 Hz, 1H), 7.45-7.31 (m, 7H), 7.18 (d, J=7.7 Hz, 2H), 4.89 (bs, 2H), 4.24 (s, 3H), 2.48-2.35 (m, 2H), 2.22-2.12 (m, 2H), 2.05-1.94 (m, 1H), 1.72-1.59 (m, 1H). LCMS (Method E): RT=3.16 min, [M+H]+=422.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-5e417f26910947c1b4ac1a1452ff1aaa
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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