Hydrochloric Acid → 7-[4-(1-Amino-cyclobutyl)-phenyl]-2-methyl-8-phenyl-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione hydrochloride

HRID 1037318Notes

Reaction equation

HRID 1037318 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[CH:50]=[CH:51][N:52]5[C:65](=[O:66])[N:64]([CH3:67])[N:63]=[C:53]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:77]>CO.O>[ClH:77].[NH2:36][C:37]1([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[C:48](=[O:68])[C:49]4[CH:50]=[CH:51][N:52]5[C:65](=[O:66])[N:64]([CH3:67])[N:63]=[C:53]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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 86671043{1-[4-(2-Methyl-3,6-dioxo-8-phenyl-2,6-dihydro-3H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalen-7-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 866710447-[4-(1-Amino-cyclobutyl)-phenyl]-2-methyl-8-phenyl-2H-9-oxa-1,2,3a-triaza-cyclopenta[a]naphthalene-3,6-dione hydrochlorideYield 77%

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-methyl-3,6-dioxo-8-phenyl-2,6-dihydro-3H-9-oxa-1,2,3a-triaza-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 (1.5 mL), water (3.5 mL) and 1 M HCl (0.1 mL) and chromatographed on a 5 g C18 cartridge {30 to 70% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (13.5 mg, 77%). 1H NMR (400 MHz, DMSO-d6): δ 8.62 (br s, 3H), 7.86 (d, J=7.2 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.47-7.37 (m, 5H), 7.30 (d, J=8.3 Hz, 2H), 7.00 (d, J=7.2 Hz, 1H), 3.65 (s, 3H), 2.61-2.49 (m, 4H), 2.23-2.12 (m, 1H), 1.85-1.74 (m, 1H). LCMS (Method E): RT=2.95 min, [M+H]+=439.

Workup

  1. customchromatographed on a 5 g C18 cartridge

Sources & evidence

ORD record
ord-83462eb0d2d84f289edbf0b06062d45a
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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