Hydrochloric Acid → HCID 67067984, compound

HRID 1037357Notes

Reaction equation

HRID 1037357 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]([CH2:66][CH2:67][OH:68])[N:64]=[CH:65][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]([CH2:66][CH2:67][OH:68])[N:64]=[CH:65][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 67067733HCID 67067733, compound

Product 1

HCID 67067984HCID 67067984, compoundYield 74%

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-[1-(2-hydroxy-ethyl)-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 (8 mL) and 1 M HCl (0.2 mL) and chromatographed on a 5 g C18 cartridge {gradient 20 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound (33.5 mg, 74%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.60 (br s, 3H), 8.33 (s, 1H), 7.81 (d, J=8.6 Hz, 1H), 7.75 (d, J=8.5 Hz, 1H), 7.57-7.55 (m, 2H), 7.51-7.37 (m, 5H), 7.32 (d, J=8.4 Hz, 2H), 4.95 (t, J=5.1 Hz, 1H), 4.80 (t, J=5.6 Hz, 2H), 3.89 (q, J=5.5 Hz, 2H), 2.63-2.52 (m, 4H), 2.24-2.13 (m, 1H), 1.87-1.76 (m, 1H). LCMS (Method E): RT=3.00 min, [M+H]+=452.

Workup

  1. customchromatographed on a 5 g C18 cartridge {gradient 20 to 60% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)}

Sources & evidence

ORD record
ord-2757e1cf4bb34124883d6e4819cd91d8
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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