4-(Chloromethyl)-2-(2-chlorophenyl)-5-methyloxazole → Rac-3-{1-[2-(2-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-1h-indol-5-yl}-2-phenoxy-propionic acid

HRID 2181242Notes

Reaction equation

HRID 2181242 reaction equation
C[O:2][C:3](=[O:22])[CH:4]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2.Cl[CH2:24][C:25]1[N:26]=[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[Cl:37])[O:28][C:29]=1[CH3:30]>>[Cl:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:27]1[O:28][C:29]([CH3:30])=[C:25]([CH2:24][N:11]2[C:12]3[C:8](=[CH:7][C:6]([CH2:5][CH:4]([O:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[C:3]([OH:2])=[O:22])=[CH:14][CH:13]=3)[CH:9]=[CH:10]2)[N:26]=1

Participants

3

Reactant 2

HCID 219742564-(Chloromethyl)-2-(2-chlorophenyl)-5-methyloxazoleHCID 69563280Rac-3-(1h-indol-5-yl)-2-phenoxy-propionic acid methyl ester

Product 1

HCID 10005663Rac-3-{1-[2-(2-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-1h-indol-5-yl}-2-phenoxy-propionic acid

Procedure

In analogy to the procedure described in example 44, rac-3-(1H-indol-5-yl)-2-phenoxy-propionic acid methyl ester (preparation 7) was reacted with 4-chloromethyl-2-(2-chloro-phenyl)-5-methyl-oxazole to give rac-3-{1-[2-(2-chloro-phenyl)-5-methyl-oxazol-4-ylmethyl]-1H-indol-5-yl}-2-phenoxy-propionic acid as off-white solid.

Sources & evidence

ORD record
ord-ff384bcf907d46ee896a4ca7425db9d4
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

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