Hydrochloric Acid → HCID 68227506, compound

HRID 1037391Notes

Reaction equation

HRID 1037391 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:69])[C:49]4[C:54]([O:55][C:56]=3[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[C:53]3[N:63]([CH3:68])[N:64]=[C:65]([CH2:66][CH3:67])[C:52]3=[CH:51][CH:50]=4)=[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:48](=[O:69])[C:49]4[C:54]([O:55][C:56]=3[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[C:53]3[N:63]([CH3:68])[N:64]=[C:65]([CH2:66][CH3:67])[C:52]3=[CH:51][CH:50]=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 67067952HCID 67067952, compound

Product 1

HCID 68227506HCID 68227506, compoundYield 43%

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-(3-ethyl-1-methyl-6-oxo-8-phenyl-1,6-dihydro-9-oxa-1,2-diaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester was treated with TFA. The resultant free base was dissolved in a mixture of MeOH (2 mL), water (3 mL) and 1 M HCl (0.1 mL) and chromatographed on a 2 g C18 cartridge {gradient 40 to 65% MeOH in water+1 M HCl (60 μL in each 5 mL of eluent)} to give the title compound (9 mg, 43%, 3 steps) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.38 (br s, 3H), 7.80 (d, J=8.6 Hz, 1H), 7.70 (d, J=8.6 Hz, 1H), 7.55-7.53 (m, 2H), 7.50-7.43 (m, 3H), 7.41-7.37 (m, 2H), 7.32 (d, J=8.3 Hz, 2H), 4.34 (s, 3H), 2.99 (q, J=7.6 Hz, 2H), 2.63-2.52 (m, 4H), 2.22-2.11 (m, 1H), 1.87-1.76 (m, 1H), 1.35 (t, J=7.6 Hz, 3H). LCMS (Method E): RT=3.79 min, [M+H]+=450.

Workup

  1. customchromatographed on a 2 g C18 cartridge {gradient 40 to 65% MeOH in water+1 M HCl (60 μL in each 5 mL of eluent)}

Sources & evidence

ORD record
ord-c3924fad95884342aaf61536d1e6567d
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

Loading…