Trifluoroacetic acid → HCID 24898137, compound

HRID 555350Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:40])/[C:10](/[CH2:28][O:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)=[CH:11]/[C:12]2[CH:27]=[CH:26][C:15]([C:16]([NH:18][O:19]C3CCCCO3)=[O:17])=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O>CO>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH:8][C:9](=[O:40])/[C:10](/[CH2:28][O:29][C:30]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32][CH:31]=2)=[CH:11]/[C:12]2[CH:13]=[CH:14][C:15]([C:16]([NH:18][OH:19])=[O:17])=[CH:26][CH:27]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 0 °C

Procedure

(E)-4-(3-(1-Methylpiperidin-4-ylamino)-2-((naphthalen-1-yloxy)-methyl)-3-oxoprop-1-enyl)-N-(tetrahydro-2H-pyran-2-yloxy)benzamide obtained in Example (1-1-3) (333 mg, 0.61 mM) was dissolved in methanol (5 ml) and the resulting solution was cooled to 0° C. To the resulting solution, trifluoroacetic acid (0.23 ml, 5 eq.) was slowly added, and the resultant was reacted at room temperature for 18 hrs. After the completion of reaction, the solvent was removed under reduced pressure. The residue thus obtained was purified with a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/1) to obtain 250 mg of the title compound as a white solid (yield 89%).

Workup

customthe resultant was reacted at room temperature for 18 hrs
customAfter the completion of reaction
customthe solvent was removed under reduced pressure
customThe residue thus obtained
customwas purified with a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/1)

Sources & evidence

ORD record: ord-bfd5543709f349e6a10f4a7df039a774
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08053435B2

Reaction notes

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