Hydrochloric Acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-8-morpholin-4-yl-2-phenyl-chromen-4-one hydrochloride

HRID 1037335Notes

Reaction equation

HRID 1037335 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]([N:58]5[CH2:63][CH2:62][O:61][CH2:60][CH2:59]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.[ClH:78]>CO.O>[ClH:78].[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](=[C:51]([N:58]5[CH2:63][CH2:62][O:61][CH2:60][CH2:59]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:45][CH:46]=2)[CH2:40][CH2:39][CH2:38]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067829{1-[4-(8-Morpholin-4-yl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 670677533-[4-(1-Amino-cyclobutyl)-phenyl]-8-morpholin-4-yl-2-phenyl-chromen-4-one hydrochlorideYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Following the procedure of 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, {1-[4-(8-morpholin-4-yl-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was dissolved in a mixture of MeOH (7 mL), water (7 mL) and 1 M HCl (0.6 mL) and chromatographed on a 5 g C18 cartridge {gradient 10 to 50% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (23 mg, 75%). 1H NMR (400 MHz, DMSO-d6): δ 8.47 (bs, 3H), 7.67 (dd, J=7.5 and 2.1 Hz, 1H), 7.45-7.29 (m, 9H), 7.25 (d, J=8.3 Hz, 2H), 3.74 (t, J=4.1 Hz, 4H), 3.13 (t, J=3.6 Hz, 4H), 2.58-2.44 (m, 4H), 2.19-2.06 (m, 1H), 1.82-1.70 (m, 1H). LCMS (Method E): RT=3.44 min, [M+H]+=453.

Workup

  1. customchromatographed on a 5 g C18 cartridge {gradient 10 to 50% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)}

Sources & evidence

ORD record
ord-08614ae231334f4e85ebca906c13e4ee
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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