3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(1-Amino-cyclobutyl)-phenyl]-8-methyl-2-phenyl-8H-pyrano[2,3-e]indazol-4-one

HRID 1037302Notes

Reaction equation

HRID 1037302 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:57]=[CH:56][C:55]5[C:51](=[CH:52][N:53]([CH3:58])[N:54]=5)[C:50]=4[O:59][C:60]=3[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=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:46]=[CH:45][C:44]([C:47]3[C:48](=[O:67])[C:49]4[CH:57]=[CH:56][C:55]5[C:51](=[CH:52][N:53]([CH3:58])[N:54]=5)[C:50]=4[O:59][C:60]=3[C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)=[CH:43][CH:42]=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 67067704{1-[4-(8-Methyl-4-oxo-2-phenyl-4,8-dihydro-pyrano[2,3-e]indazol-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510299533-[4-(1-Amino-cyclobutyl)-phenyl]-8-methyl-2-phenyl-8H-pyrano[2,3-e]indazol-4-oneYield 89%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(8-methyl-4-oxo-2-phenyl-4,8-dihydro-pyrano[2,3-e]indazol-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a white solid (15 mg, 89%). 1H NMR (400 MHz, DMSO-d6): δ 8.96 (s, 1H), 7.82 (d, J=9.4 Hz, 1H), 7.62 (d, J=9.4 Hz, 1H), 7.49-7.40 (m, 5H), 7.39-7.33 (m, 2H), 7.25-7.21 (m, 2H), 4.23 (s, 3H), 2.51-2.42 (m, 2H), 2.37-2.28 (m, 2H), 2.13-2.03 (m, 1H), 1.77-1.64 (m, 1H). LCMS (Method E): RT=3.13 min, [M+H]+=422.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-1a8cd93b3e33464b96cc9e9804eef85d
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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