2-methoxy-5-(5-pyrimidinyl)Benzaldehyde → HCID 67668087, compound

HRID 1289985Notes

Reaction equation

HRID 1289985 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].[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[N:32][CH:33]=[N:34][CH:35]=2)=[CH:26][C:23]=1[CH:24]=O>>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([NH:10][CH2:24][C:23]2[CH:26]=[C:27]([C:30]3[CH:35]=[N:34][CH:33]=[N:32][CH:31]=3)[CH:28]=[CH:29][C:22]=2[O:21][CH3:20])[CH:6]1[C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)=[O:4]

Participants

3

Reactant 2

HCID 107273552-methoxy-5-(5-pyrimidinyl)BenzaldehydeHCID 18922366HCID 18922366, compound

Product 1

HCID 67668087HCID 67668087, 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 Ex. 89, Step A) and the known 2-methoxy-5-(pyrimidin-5-yl)benzaldehyde (P. J. Ward, et al., J. Med. Chem. 1995, 38, 4985-92). 1H NMR (400 MHz, CD3OD): δ 9.07 (s, 1H), 8.99 (s, 2H), 7.61 (dd, 1H, J=9,2 Hz), 7.45 (d, 1H, J=2 Hz), 7.22 (dd, 2H, J=9,5 Hz), 7.07 (t, 2H, J=9 Hz), 7.02 (d, 1H, J=9 Hz), 3.76 (d, 1H, J=13 Hz), 3.59 (s, 3H), 3.56 (s, 3H), 3.55-3.49 (m, 1H), 3.53 (d, 1H, J=13 Hz), 3.45-3.36 (m, 1H), 3.26 (td, 1H, J=6,2 Hz), 2.36-2.26 (m, 1H), 2.12-2.01 (m, 1H), 1.99-1.88 (m, 2H). Mass spectrum (NH3 /CI): 436 (M+1).

Sources & evidence

ORD record
ord-5deb7a1c60d4452cbddf2e41ae901230
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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