Hydrochloric Acid → HCID 67067837, compound

HRID 1037347Notes

Reaction equation

HRID 1037347 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:68])[C:49]4[C:50]([O:60][C:61]=3[C:62]3[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=3)=[C:51]([C:55]3[CH:56]=[N:57][NH:58][CH:59]=3)[N:52]=[CH:53][CH:54]=4)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C.C(O)(C(F)(F)F)=O.[ClH:77]>CO.O>[ClH:77].[NH2:36][C:37]1([C:41]2[CH:42]=[CH:43][C:44]([C:47]3[C:48](=[O:68])[C:49]4[C:50]([O:60][C:61]=3[C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=3)=[C:51]([C:55]3[CH:56]=[N:57][NH:58][CH:59]=3)[N:52]=[CH:53][CH:54]=4)=[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 67067803HCID 67067803, compound

Product 1

HCID 67067837HCID 67067837, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Following the procedure used to prepare 3-[4-(1-amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-one, (1-{4-[4-oxo-2-phenyl-8-(1H-pyrazol-4-yl)-4H-pyrano[2,3-c]pyridin-3-yl]-phenyl}-cyclobutyl)-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was dissolved in a mixture of MeOH (0.75 mL), water (4.25 mL) and 1 M HCl (0.1 mL) and then chromatographed on a 2 g C18 cartridge {gradient 15 to 50% MeOH in water+1 M HCl (60 μL in each 5 mL of eluent)} to give the title compound as a white solid (12.1 mg, 81%, 2 steps). 1H NMR (400 MHz, DMSO-d6): δ 8.66 (d+br s, J=5.1 Hz, 4H), 8.29 (s, 2H), 7.80 (d, J=5.0 Hz, 1H), 7.55-7.41 (m, 7H), 7.30 (d, J=8.2 Hz, 2H), 2.59-2.51 (m, 4H), 2.23-2.12 (m, 1H), 1.85-1.74 (m, 1H). LCMS (Method E): RT=2.79 min, [M+H]+=435.

Workup

  1. customchromatographed on a 2 g C18 cartridge {gradient 15 to 50% MeOH in water+1 M HCl (60 μL in each 5 mL of eluent)}

Sources & evidence

ORD record
ord-e390ed84300347bfa19cf377967d40a5
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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