3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → HCID 51030975, compound

HRID 1037224Notes

Reaction equation

HRID 1037224 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:56](=[O:57])[C:55]4[C:50](=[CH:51][C:52]([C:60]5[NH:61][N:62]=[CH:63][CH:64]=5)=[C:53]([O:58][CH3:59])[CH:54]=4)[O:49][C:48]=3[C:65]3[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=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:42]=[CH:43][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[CH:51][C:52]([C:60]5[NH:61][N:62]=[CH:63][CH:64]=5)=[C:53]([O:58][CH3:59])[CH:54]=4)[O:49][C:48]=3[C:65]3[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=3)=[CH:45][CH:46]=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 68227221(1-{4-[6-Methoxy-4-oxo-2-phenyl-7-(2H-pyrazol-3-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 51030975HCID 51030975, compoundYield 75%

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{4-[6-methoxy-4-oxo-2-phenyl-7-(2H-pyrazol-3-yl)-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester was reacted to give the title compound as a pale yellow solid (34 mg, 75%). 1H NMR (400 MHz, DMSO-d6): δ 13.32-13.18 (br s, 1H), 8.21 (s, 1H), 7.88-7.72 (br s, 1H), 7.60-7.56 (br s, 1H), 7.44-7.30 (m, 7H), 7.19-7.14 (m, 2H), 6.97 (s, 1H), 4.01 (s, 3H), 2.45-2.36 (m, 2H), 2.20-2.10 (m, 2H), 2.08-1.97 (m, 1H), 1.72-1.61 (m, 1H). LCMS (Method E): RT=3.39 min, [M+H]+=464.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-bf0d1dcbc6ce45678d2e1f3e474f0e93
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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