3-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-7H-pyrano[2,3-e]indazol-4-one → 7-[4-(1-Amino-cyclobutyl)-phenyl]-8-phenyl-3H-chromeno[7,8-d]oxazole-2,6-dione

HRID 1037374Notes

Reaction equation

HRID 1037374 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:54](=[O:55])[C:53]4[CH:56]=[CH:57][C:58]5[NH:59][C:60](=[O:63])[O:61][C:62]=5[C:52]=4[O:51][C:50]=3[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=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:54](=[O:55])[C:53]4[CH:56]=[CH:57][C:58]5[NH:59][C:60](=[O:63])[O:61][C:62]=5[C:52]=4[O:51][C:50]=3[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=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 67067764(1-[4-(2,6-Dioxo-8-phenyl-3,6-dihydro-2H-chromeno[7,8-d]oxazol-7-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510305137-[4-(1-Amino-cyclobutyl)-phenyl]-8-phenyl-3H-chromeno[7,8-d]oxazole-2,6-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-(2,6-dioxo-8-phenyl-3,6-dihydro-2H-chromeno[7,8-d]oxazol-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 7.64 (d, J=8.2 Hz, 1H), 7.43-7.38 (m, 5H), 7.37-7.31 (m, 2H), 7.26-7.22 (m, 2H), 7.02 (d, J=8.2 Hz, 1H), 2.58-2.49 (m, 2H), 2.42-2.32 (m, 2H), 2.16-2.05 (m, 1H), 1.82-1.71 (m, 1H). LCMS (Method E): RT=3.08 min, [M+H]+=425.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-ffc8e7b6660e454facc0e186c5d089e1
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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