Hydrochloric Acid → 3-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-chromen-4-one O-methyl-oxime hydrochloride

HRID 1037323Notes

Reaction equation

HRID 1037323 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:56](=[N:57][O:58][CH3:59])[C:55]4[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=4)[O:49][C:48]=3[C:60]3[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=3)=[CH:43][CH:42]=2)[CH2:40][CH2:39][CH2:38]1)(C)(C)C.C(O)(C(F)(F)F)=O.[ClH:74]>CO.O>[ClH:74].[CH3:59][O:58][N:57]=[C:56]1[C:55]2[C:50](=[CH:51][CH:52]=[CH:53][CH:54]=2)[O:49][C:48]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[C:47]1[C:44]1[CH:43]=[CH:42][C:41]([C:37]2([NH2:36])[CH2:40][CH2:39][CH2:38]2)=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 510305983-[4-(1-Amino-cyclobutyl)-phenyl]-6-fluoro-2-phenyl-chromen-4-oneHCID 86671048{1-[4-(4-Methoxyimino-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 866710493-[4-(1-Amino-cyclobutyl)-phenyl]-2-phenyl-chromen-4-one O-methyl-oxime hydrochlorideYield 69%

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-methoxyimino-2-phenyl-4H-chromen-3-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 (6 mL) and 1 M HCl (0.1 mL) and chromatographed on a 5 g C18 cartridge {35 to 80% MeOH in water+1 M HCl (60 μL in each 10 mL of eluent)} to give the title compound as a white solid (13.3 mg, 69%). 1H NMR (400 MHz, CD3OD): δ 8.89 (dd, J=8.4 and 1.4 Hz, 1H), 7.54-7.50 (m, 1H), 7.39 (d, J=8.4 Hz, 2H), 7.33-7.16 (m, 9H), 3.77 (s, 3H), 2.80-2.73 (m, 2H), 2.60-2.52 (m, 2H), 2.28-2.17 (m, 1H), 2.01-1.90 (m, 1H). LCMS (Method E): RT=4.10 min, [M+H]+=397.

Workup

  1. customchromatographed on a 5 g C18 cartridge

Sources & evidence

ORD record
ord-a9c1fa7921ef4901a4f16d5988b3bc38
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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