1-Methyl-2-imidazolecarboxaldehyde → 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyl-3-[(1-methyl-1H-imidazol-2-yl)methyl]dihydro-2H-pyran-2,4(3H)-dione
Reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH:7]=O.CC1C=C(C)N2N=C(C=O)N=C2N=1.[Cl:22][C:23]1[CH:24]=[C:25]([CH2:31][CH2:32][C:33]2([CH:41]3[CH2:45][CH2:44][CH2:43][CH2:42]3)[O:38][C:37](=[O:39])[CH2:36][C:35](=[O:40])[CH2:34]2)[CH:26]=[CH:27][C:28]=1[O:29][CH3:30].ClC1C=C(CCC2(C3CCCC3)OC(=O)CC(=O)C2)C=CC=1OC(C)C>>[Cl:22][C:23]1[CH:24]=[C:25]([CH2:31][CH2:32][C:33]2([CH:41]3[CH2:45][CH2:44][CH2:43][CH2:42]3)[O:38][C:37](=[O:39])[CH:36]([CH2:7][C:3]3[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=3)[C:35](=[O:40])[CH2:34]2)[CH:26]=[CH:27][C:28]=1[O:29][CH3:30]Participants
Reactant 4
Product 1
Procedure
The title compound was prepared analogously to Example B(31), where 1-methyl-1H-imidazole-2-carbaldehyde was substituted in place of 5,7-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine-2-carbaldehyde and 6-[2-(3-chloro-4-methoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione was substituted in place of 6-[2-(3-chloro-4-isopropoxyphenyl)ethyl]-6-cyclopentyldihydro-2H-pyran-2,4(3H)-dione in that example. 1H NMR (CDCl3): δ 1.44-1.70 (bm, 8H), 2.0 (m, 2H), 2.20 (m, 3H), 2.30 (m, 2H), 2.99 (m, 2H), 3.01 (M. 2H), 3.46 (s, 3H) 3.78 (m, 1H), 3.89 (s, 3H), 6.72 (d, J=2.15 Hz, 1H), 6.83, (d, J=2.15 Hz, 1H), 6.90 (s, 1H), 7.14, (d, J=3.07 Hz, 1H), 7.24 (d, J=3.06 Hz, 1H). Anal. Calcd. For C25H31O3N2Cl: C, 67.78; H, 7.05; N, 6.32. Found: C, 67.48; H, 7.25; N, 6.37.
Sources & evidence
- ORD record
- ord-30f953e0e608457db405b05e591509e3
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07473790B2
Reaction notes
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