HCID 10774463, compound → HCID 86752555, compound

HRID 1289983Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([N:10]=[N+]=[N-])[CH:6]1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[O:4].[O:20]1[CH:24]=[CH:23][C:22]([C:25]2[CH:26]=[CH:27][C:28]([O:33][CH3:34])=[C:29]([CH:32]=2)[CH:30]=O)=[CH:21]1>>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([NH:10][CH2:30][C:29]2[CH:32]=[C:25]([C:22]3[CH:23]=[CH:24][O:20][CH:21]=3)[CH:26]=[CH:27][C:28]=2[O:33][CH3:34])[CH:6]1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[O:4]

Participants

Reactant 2

HCID 10774463HCID 10774463, compound

HCID 18922366HCID 18922366, compound

Product 1

HCID 86752555HCID 86752555, compound

Procedure

The title compound was prepared by employing the method described in Example 91, Step D with (1RS,2RS,3RS)-2-(4-fluorophenyl)-3-azidocyclopentanecarboxylic acid methyl ester (from Example 89, Step A) and the known 5-(furan-3-yl)-2-methoxybenzaldehyde (P. J. Ward, et al., J. Med. Chem. 1995, 38, 4985-92). NMR (400 MHz, CDCl3): δ 7.63-7.61 (m, 1H), 7.46 (t, 1H, J=2 Hz), 7.31 (dd, 1H, J=9,2 Hz), 7.18 (dd, 2H, J=9,5 Hz), 7.12 (d, 1H, J=2 Hz), 7.01 (t, 2H, J=9 Hz), 6.75 (d, 1H, J=9 Hz), 6.62 (dd, 1H, J=2,1 Hz), 3.73 (d, 1H, J=13 Hz), 3.61 (s, 3H), 3.54 (s, 3H), 3.53-3.38 (m, 2H), 3.45 (d, 1H, J=13 Hz), 3.27-3.22 (m, 1H), 2.41-2.29 (m, 1H), 2.02-1.87 (m, 3H), 1.69 (br, 1H). Mass spectrum (NH3 /CI): 424 (M+1).

Sources & evidence

ORD record: ord-02225dd4c8004b78aacd6052353f50d5
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750549

Reaction notes

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