3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → 3-[4-(1-Amino-cyclobutyl)-phenyl]-7-methyl-2-phenyl-7H-pyrano[2,3-e]indazol-4-one

HRID 1037300Notes

Reaction equation

HRID 1037300 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[C:50]([O:59][C:60]=3[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)=[C:51]3[C:55](=[CH:56][CH:57]=4)[N:54]([CH3:58])[N:53]=[CH:52]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[C:50]([O:59][C:60]=3[C:61]3[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=3)=[C:51]3[C:55](=[CH:56][CH:57]=4)[N:54]([CH3:58])[N:53]=[CH:52]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 67067793(1-[4-(7-Methyl-4-oxo-2-phenyl-4,7-dihydro-pyrano[2,3-e]indazol-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 510299523-[4-(1-Amino-cyclobutyl)-phenyl]-7-methyl-2-phenyl-7H-pyrano[2,3-e]indazol-4-oneYield 84%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(7-methyl-4-oxo-2-phenyl-4,7-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 (28 mg, 84%). 1H NMR (400 MHz, DMSO-d6): δ 8.51 (d, J=1.0 Hz, 1H), 8.02 (d, J=8.8 Hz, 1H), 7.76 (dd, J=1.0 and 8.8 Hz, 1H), 7.52-7.48 (m, 2H), 7.45-7.34 (m, 5H), 7.20-7.16 (m, 2H), 4.17 (s, 3H), 2.45-2.36 (m, 2H), 2.20-2.11 (m, 2H), 2.07-1.96 (m, 1H), 1.73-1.61 (m, 1H). LCMS (Method E): RT=3.33 min, [M+H]+=422.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-8ce13141e4324612b671b621121dfbe4
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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