3-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one → HCID 86671033, compound

HRID 1037260Notes

Reaction equation

HRID 1037260 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:64])[C:49]4[C:50]([O:56][C:57]=3[C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[C:51]([Cl:55])[N:52]=[CH:53][CH:54]=4)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C>>[ClH:55].[NH2:36][C:37]1([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[C:48](=[O:64])[C:49]4[C:50]([O:56][C:57]=3[C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)=[C:51]([Cl:55])[N:52]=[CH:53][CH:54]=4)=[CH:45][CH:46]=2)[CH2:40][CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 86671031tert-Butyl 1-(4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)phenyl)cyclobutylcarbamate

Product 1

HCID 86671033HCID 86671033, compound

Procedure

Following the procedure of 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(8-chloro-4-oxo-2-phenyl-4H-pyrano[2,3-c]pyridin-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was reacted to give the title compound as the free base. The residue was dissolved in a mixture of MeOH (2 mL), water (3 mL) and 1 M HCl (0.1 mL) and then chromatographed on a 5 g C18 cartridge {gradient 40 to 70% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound (12.5 mg, 75%) as a white solid. 1H NMR (400 MHz, CD3OD): δ 8.45 (d, J=5.1 Hz, 1H), 8.02 (d, J=5.1 Hz, 1H), 7.53-7.48 (m, 4H), 7.46-7.41 (m, 1H), 7.39-7.32 (m, 4H), 2.82-2.75 (m, 2H), 2.63-2.55 (m, 2H), 2.30-2.19 (m, 1H), 2.03-1.92 (m, 1H). LCMS (Method E): RT=3.54 min, [M−NH2]−=386/388.

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-262586b1ca3d4cc0b907c4f2d0cdcd24
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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