3-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-one → 7-Amino-3-[4-(1-amino-cyclobutyl)-phenyl]-8-hydroxy-2-phenyl-chromen-4-one

HRID 1037380Notes

Reaction equation

HRID 1037380 reaction equation
NC1(C2C=CC(C3C(=O)C4C(OC=3C3C=CC=CC=3)=C3C(=CC=4)NN=C3)=CC=2)CCC1.C(OC(=O)[NH:38][C:39]1([C:43]2[CH:48]=[CH:47][C:46]([C:49]3[C:58](=[O:59])[C:57]4[C:52](=[C:53]([OH:61])[C:54]([NH2:60])=[CH:55][CH:56]=4)[O:51][C:50]=3[C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)=[CH:45][CH:44]=2)[CH2:42][CH2:41][CH2:40]1)(C)(C)C>>[NH2:60][C:54]1[C:53]([OH:61])=[C:52]2[C:57]([C:58](=[O:59])[C:49]([C:46]3[CH:47]=[CH:48][C:43]([C:39]4([NH2:38])[CH2:40][CH2:41][CH2:42]4)=[CH:44][CH:45]=3)=[C:50]([C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=3)[O:51]2)=[CH:56][CH:55]=1

Participants

3

Reactant 2

HCID 510295913-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-oneHCID 67067987{1-[4-(7-Amino-8-hydroxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 510305147-Amino-3-[4-(1-amino-cyclobutyl)-phenyl]-8-hydroxy-2-phenyl-chromen-4-oneYield 45%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-one, {1-[4-(7-amino-8-hydroxy-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a yellow solid (9 mg, 45%). 1H NMR (400 MHz, DMSO-d6): δ 7.48 (m, 2H), 7.39 (d, J=8.6 Hz, 1H), 7.37-7.27 (m, 5H), 7.09-7.05 (m, 2H), 6.78 (d, J=8.6 Hz, 1H), 5.76-5.69 (br s, 2H), 2.39-2.32 (m, 2H), 2.10-2.02 (m, 2H), 2.02-1.93 (m, 1H), 1.68-1.60 (m, 1H). LCMS (Method E): RT=2.81 min, [M+H]+=399.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-6e5cd2bf86624a02b79578ec21b062b2
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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