3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(1-Amino-cyclobutyl)-phenyl]-7-(2-methoxy-ethyl)-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione

HRID 1037231Notes

Reaction equation

HRID 1037231 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:68])[C:49]4[CH:54]=[CH:53][N:52]([CH2:55][CH2:56][O:57][CH3:58])[C:51](=[O:59])[C:50]=4[O:60][C:61]=3[C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=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:68])[C:49]4[CH:54]=[CH:53][N:52]([CH2:55][CH2:56][O:57][CH3:58])[C:51](=[O:59])[C:50]=4[O:60][C:61]=3[C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=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 86671020(1-{4-[7-(2-methoxy-ethyl)-4,8-dioxo-2-phenyl-7,8-dihydro-4H-pyrano[2,3-c]pyridin-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510295893-[4-(1-Amino-cyclobutyl)-phenyl]-7-(2-methoxy-ethyl)-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dioneYield 72%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{4-[7-(2-methoxy-ethyl)-4,8-dioxo-2-phenyl-7,8-dihydro-4H-pyrano[2,3-c]pyridin-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester was reacted to give the title compound as an off-white solid (48 mg, 72%). 1H NMR (400 MHz, DMSO-d6): δ 7.64 (d, J=7 Hz, 1H), 7.42-7.32 (m, 7H), 7.16-7.12 (m, 2H), 6.67 (d, J=7 Hz, 1H), 4.22 (t, J=5 Hz, 2H), 3.65 (t, J=5 Hz, 2H), 3.26 (s, 3H), 2.42-2.35 (m, 2H), 2.18-2.10 (m, 2H), 2.06-1.96 (m, 2H). LCMS (Method E): RT=2.93 min, [M+H]+=443.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-52af84a5a8d9440187aef70a47eadcb6
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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