3-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-one → 7-[4-(1-Amino-cyclobutyl)-phenyl]-6-phenyl-1H-4,5-dioxa-1-aza-phenanthrene-2,8-dione

HRID 1037377Notes

Reaction equation

HRID 1037377 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:62](=[O:63])[C:61]4[C:52](=[C:53]5[C:58](=[CH:59][CH:60]=4)[NH:57][C:56](=[O:64])[CH2:55][O:54]5)[O:51][C:50]=3[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:45][CH:44]=2)[CH2:42][CH2:41][CH2:40]1)(C)(C)C>>[NH2:38][C:39]1([C:43]2[CH:44]=[CH:45][C:46]([C:49]3[C:62](=[O:63])[C:61]4[C:52](=[C:53]5[C:58](=[CH:59][CH:60]=4)[NH:57][C:56](=[O:64])[CH2:55][O:54]5)[O:51][C:50]=3[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=3)=[CH:47][CH:48]=2)[CH2:42][CH2:41][CH2:40]1

Participants

3

Reactant 2

HCID 510295913-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-oneHCID 67067975{1-[4-(2,8-Dioxo-6-phenyl-1,2,3,8-tetrahydro-4,5-dioxa-1-aza-phenanthren-7-yl)-phenyl]cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 670676307-[4-(1-Amino-cyclobutyl)-phenyl]-6-phenyl-1H-4,5-dioxa-1-aza-phenanthrene-2,8-dioneYield 58%

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-(2,8-dioxo-6-phenyl-1,2,3,8-tetrahydro-4,5-dioxa-1-aza-phenanthren-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as a white solid (31 mg, 58%). 1H NMR (400 MHz, DMSO-d6): δ 7.69 (d, J=8.8 Hz, 1H), 7.42-7.30 (m, 7H), 7.12-7.09 (m, 2H), 7.04 (d, J=8.8 Hz, 1H), 4.80 (s, 2H), 2.39-2.31 (m, 2H), 2.10-2.01 (m, 2H), 2.01-1.93 (m, 1H), 1.69-1.57 (m, 1H). LCMS (Method E): RT=3.03 min, [M+H]+=439.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-a2830b3d66124c61bef72923b6745bb7
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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