Hydrochloric Acid → HCID 67067981, compound

HRID 1037355Notes

Reaction equation

HRID 1037355 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[CH:50]=[CH:51][C:52]5[C:53](=[N:63][N:64]([CH:66]([CH3:68])[CH3:67])[CH:65]=5)[C:54]=4[O:55][C:56]=3[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=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:48](=[O:69])[C:49]4[CH:50]=[CH:51][C:52]5[C:53](=[N:63][N:64]([CH:66]([CH3:67])[CH3:68])[CH:65]=5)[C:54]=4[O:55][C:56]=3[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=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 67068027HCID 67068027, compound

Product 1

HCID 67067981HCID 67067981, compoundYield 71%

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-(2-isopropyl-6-oxo-8-phenyl-2,6-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 (3 mL), water (7 mL) and 1 M HCl (0.2 mL) and chromatographed on a 5 g C18 cartridge {gradient 30 to 70% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound (30.2 mg, 71%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.70 (s, 1H), 8.54 (br s, 3H), 7.74 (d, J=8.8 Hz, 1H), 7.63 (d, J=8.8 Hz, 1H), 7.50-7.38 (m, 7H), 7.32 (d, J=8.3 Hz, 2H), 4.96 (septet, J=6.7 Hz, 1H), 2.61-2.49 (m, 4H), 2.23-2.12 (m, 1H), 1.86-1.75 (m, 1H), 1.60 (d, J=6.7 Hz, 6H). LCMS (Method E): RT=3.58 min, [M+H]+=450.

Workup

  1. customchromatographed on a 5 g C18 cartridge {gradient 30 to 70% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)}

Sources & evidence

ORD record
ord-f2160d538f8b4010815b4b840b939f11
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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