4-(1,2,3-Thiadiazol-4-yl)benzaldehyde → 6-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-3-(4-[1,2,3]thiadiazol-4-yl-benzyl)-5,6-dihydro-pyran-2-one

HRID 858711

Reaction equation

HRID 858711 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[S:25]1[CH:29]=[C:28]([C:30]2[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=2)[N:27]=[N:26]1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[C:15]([CH2:34][C:33]3[CH:36]=[CH:37][C:30]([C:28]4[N:27]=[N:26][S:25][CH:29]=4)=[CH:31][CH:32]=3)=[C:14]([OH:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

3

Reactant 2

HCID 27764534-(1,2,3-Thiadiazol-4-yl)benzaldehydeHCID 160761096-(3-chloro-4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dione

Product 1

HCID 587627156-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-4-hydroxy-3-(4-[1,2,3]thiadiazol-4-yl-benzyl)-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared by coupling the 6-[2-(3-Chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione to 4-[1,2,3]thiadiazol-4-yl-benzaldehyde using the Me2NHBH3 method described in the synthesis of Example B(31).

Sources & evidence

ORD record
ord-a80d626505434dfa8d1f9ad8d1cc3a92
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Linked notes

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