3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(3-Amino-oxetan-3-yl)-phenyl]-8-bromo-2-phenyl-chromen-4-one

HRID 1037325Notes

Reaction equation

HRID 1037325 reaction equation
NC1(C2C=CC(C3C(=O)C4C(=CC=C(F)C=4)OC=3C3C=CC=CC=3)=CC=2)CCC1.[Br:30][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:40]=1[O:39][C:38]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[C:37]([C:47]1[CH:52]=[CH:51][C:50]([C:53]3([NH:57]S(C(C)(C)C)=O)[CH2:56][O:55][CH2:54]3)=[CH:49][CH:48]=1)[C:36]2=[O:64]>>[NH2:57][C:53]1([C:50]2[CH:51]=[CH:52][C:47]([C:37]3[C:36](=[O:64])[C:35]4[C:40](=[C:31]([Br:30])[CH:32]=[CH:33][CH:34]=4)[O:39][C:38]=3[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)=[CH:48][CH:49]=2)[CH2:56][O:55][CH2:54]1

Participants

3

Reactant 2

HCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 670677152-Methyl-propane-2-sulfinic acid {3-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-oxetan-3-yl}-amide

Product 1

HCID 510300443-[4-(3-Amino-oxetan-3-yl)-phenyl]-8-bromo-2-phenyl-chromen-4-oneYield 34%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, 2-methyl-propane-2-sulfinic acid {3-[4-(8-bromo-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-oxetan-3-yl}-amide was reacted to give the title compound as a white solid (16 mg, 34%). 1H NMR (400 MHz, DMSO-d6): δ 8.18 (dd, J=7.8 and 1.6 Hz, 1H), 8.11 (dd, J=8.2 and 1.9 Hz, 1H), 7.54 (d, J=8.7 Hz, 2H), 7.50-7.34 (m, 6H), 7.23 (d, J=8.5, 2H), 4.71 (d, J=6.1 Hz, 2H), 4.67 (d, J=6.1 Hz, 2H), 3.32 (s, 2H). LCMS (Method E): RT=3.67 min, [M+H]+=448/450.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-ab7ba469aa3440b4933dc0ce7ffb38bf
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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