Hydrochloric Acid → HCID 67067844, compound

HRID 1037339Notes

Reaction equation

HRID 1037339 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]([C:58]5[CH:59]=[N:60][N:61]([CH3:64])[C:62]=5[CH3:63])[CH:52]=[CH:53][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.C(O)(C(F)(F)F)=O.[ClH:79]>CO.O>[ClH:79].[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]([C:58]5[CH:59]=[N:60][N:61]([CH3:64])[C:62]=5[CH3:63])[CH:52]=[CH:53][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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 67067748HCID 67067748, compound

Product 1

HCID 67067844HCID 67067844, compoundYield 65%

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-(1,5-dimethyl-1H-pyrazol-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, 65%). 1H NMR (400 MHz, DMSO-d6): δ 8.61 (s, 3H), 8.01 (dd, J=7.9 and 1.7 Hz, 1H), 7.71 (dd, J=7.3 and 1.6 Hz, 1H), 7.67 (s, 1H), 7.53 (t, J=7.6 Hz, 1H), 7.42 (d, J=8.4 Hz, 2H), 7.37-7.22 (m, 7H), 3.74 (s, 3H), 2.57-2.43 (m, 4H), 2.22 (s, 3H), 2.19-2.05 (m, 1H), 1.81-1.69 (m, 1H). LCMS (Method E): RT=3.29 min, [M+H]+=462.

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-6c0c4493c7e34761ba139e29e4599500
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…