Methanol → 3-[4-(1-Amino-cyclobutyl)-phenyl]-8-(3-fluoro-azetidin-1-ylmethyl)-2-phenyl-chromen-4-one

HRID 1037411Notes

Reaction equation

HRID 1037411 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](=[C:51]([CH2:58][N:59]5[CH2:62][CH:61]([F:63])[CH2:60]5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[NH2:36][C:37]1([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:56](=[O:57])[C:55]4[C:50](=[C:51]([CH2:58][N:59]5[CH2:62][CH:61]([F:63])[CH2:60]5)[CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)=[CH:43][CH:42]=2)[CH2:38][CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067892(1-{4-[8-(3-fluoro-azetidin-1-ylmethyl)-4-oxo-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester

Product 1

HCID 670680573-[4-(1-Amino-cyclobutyl)-phenyl]-8-(3-fluoro-azetidin-1-ylmethyl)-2-phenyl-chromen-4-oneYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{4-[8-(3-fluoro-azetidin-1-ylmethyl)-4-oxo-2-phenyl-4H-chromen-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was subjected to flash chromatography (SiO2, gradient 0 to 15% MeOH in DCM) to afford the title compound as a white solid (13 mg, 57%). 1H NMR (400 MHz, DMSO-d6): δ 7.97 (dd, J=8.0 and 1.7 Hz, 1H), 7.74 (dd, J=7.1 and 1.4 Hz, 1H), 7.47-7.28 (m, 8H), 7.08 (d, J=8.2 Hz, 2H), 5.27-5.06 (m, 1H), 3.94 (s, 2H), 3.65-3.56 (m, 2H), 3.29-3.16 (m, 2H), 2.36-2.27 (m, 2H), 2.11-1.87 (m, 5H), 1.65-1.54 (m, 1H). LCMS (Method E): RT=2.31 min, [M+H]+=455.

Sources & evidence

ORD record
ord-b4122f030b2c48efbe4a06477156a704
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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